The New Boss
By Suzi (Johnson) Thomas
We had been told that a person had been hired to fill the manager's opening we had, and we knew that she was starting today, but when she walked in the door, I think every guy in the place gave a collective gasp. Wendy was absolutely drop-dead gorgeous. She reminded me of Linda Carter, a tall brunette with a figure that even her very business-like suit couldn't really conceal. And no yuppie sneakers for her - her long, shapely legs were in sheer nylons and high-heeled pumps with at least a three-inch heel. Well, at least the scenery around here would improve, I thought to myself.
She said a collective, "Good morning" to us all, and went into her office. About a half-hour later, she had a group meeting, introducing herself, etc. I could tell from the reactions of the guys that they were entranced by her, and, while I wouldn't have kicked her out of bed by any means, I firmly believed that work and social life had to be kept entirely separate. Each was difficult enough, without mixing the two.
A couple of weeks passed, and she began having one-on-one sessions with each of us. She had learned the basics of what we did, she explained, and now she wanted to get to know each of us
better. I was pretty far down on the appointment schedule, so I had plenty of feedback from the other guys before my session. She had kept them mostly business, asking just a few questions about families and hobbies. So I was pretty surprised when she started my interview off with, "Bobby, I get the feeling that you don't particularly like me. I was wondering if it was something I've done?" Of course it was nothing of the kind, just that while the rest of the guys had been fawning over her like moon-struck calves, I had kept my distance and been, I had thought, very
professional. Without referring to the others directly, I explained my conviction to her, and she nodded that she understood. "Well, I just wanted to make sure, Bobby, but I certainly understand and can appreciate how you feel."
I must admit that it would have been easy for me to get interested in her, because once in a while I fantasized about her, and had even found myself dreaming about her once or twice. The rest of the session went along the same lines that the guys had told me about, though, and I put it out of my mind, or at least tried to. Maybe if I hadn't been between girlfriends at the time, things might have been different, but...
As the next month or so passed, I found my thoughts turning to her, and my fantasies increased in both number and intensity. Wendy never did anything to encourage them, but my imagination didn't need any reinforcement from her. There was a quarterly industry conference coming up, and I knew she'd be attending it, but one day she called me into her office, and asked if I would like to go as well. I hadn't expected this, but she told me that she had noticed my work was excellent, and felt I deserved a small break from routine. I told her that I appreciated it, and would be glad to go. Hey, a week in San Francisco was nothing to sneeze at, especially when the company was paying for it.
The following Sunday afternoon I met her at the airport, and we were soon airborne. We sat next to each other, and after a little while she asked if I minded if she picked up the armrest that was
between us, to give us a bit more room. I said, "sure", and became even more conscious of her presence beside me. We talked for a while, and then she said she was going to try to take a
nap. I was reading a book, and about an hour later, she shifted in her sleep, and her body was now resting against mine.
I got an erection almost immediately, as my mind went into fantasy mode. I pictured her naked lying next to me, but I kept myself very still, so I wouldn't cause her to shift away. She moved again, snuggling closer, and I could feel her breast against my arm. This sent waves of excitement through me, and I had to struggle to stay still, but I did. She slept almost all the way, turning away from me about fifteen minutes before she woke up, so that our bodies were no longer touching. I could still feel her there in my mind though, and my fantasies continued.
When the pilot announced that we were starting to descend, I got up and went to the restroom, carefully concealing my hard-on. I looked at myself in the mirror, and willed it to go away, but it
took quite a while as the thoughts of her firm breast against me kept coming back. When I returned to my seat, she smiled at me, and apologized for being such poor company. "Oh, don't worry about it," I said, "I was just reading my book anyway." We landed and went to the baggage claim area to wait for our bags. Hers appeared almost immediately, but mine took a long time to hit the conveyor belt. Finally they did, though, and we got our rental car, drove to the hotel and tried to check in. There had apparently been a mix-up in the reservations, and they had nothing showing for either of us.
Wendy was upset at the fact there were no single rooms left, but fortunately the manager intervened, and gave us a two-bedroom suite for the price of the rooms. As we went upstairs, Wendy apologized that we would be sharing the suite, sacrificing some privacy, but I assured her that we'd really be more comfortable anyway, since neither of us would have had the living room area, if we had had single rooms. We brought our bags in, and went into the bedrooms to unpack. A while later, she called out to me, asking if I wanted to go to dinner. I said, "sure," and we changed into more formal clothes from the casual clothes we had worn on the plane. I shaved, and then put on a suit, and when I went into the living room, she complimented me on how nice I
looked. I returned the compliment, which was easy, because she looked magnificent in a close fitting knit dress and heels.
The concierge downstairs recommended a restaurant to us, and we walked a few blocks and went in. He had apparently gotten the wrong impression, and thought that we were romantically involved, because the place was an intimate little room with booths for couple that gave the impression of privacy. We both had the same thought I guess, and laughed about it as we sat down. Wendy was an easy person to talk to, and we had a nice conversation as we ate. She asked if I wanted to order a second bottle of wine, because she felt like another glass, and we were soon deeply into the bottle. I felt a little high by then, and reaching for a new topic of conversation, I said, "You know, Wendy, I was a little worried out at the airport that my luggage had gotten lost. That would have been something, if the only thing I had to wear all week were the clothes I had on."
She laughed, and as we paid the check and were walking back, she said, "Bobby, that really would have been some problem, if your luggage had been lost. The conference starts first thing in the morning, and you wouldn't have been able to get anything to wear."
By this time we were back in the suite, and she went over to the mini-bar and took out a liqueur for a nightcap. "Want something, Bobby?" she offered. I accepted a Grand Marnier, even though I was still feeling high from the wine. We sat down on the couch, at opposite ends, though, and I brought up the luggage incident we'd been talking about before.
"I really don't know what I would have done," I said, and then jokingly continued, "if I was with one of the guys, I could probably have borrowed something from him, but I don't think I could borrow anything suitable from you."
"Why, Bobby," she teased back, "I'm hurt that you don't feel I'm one of the `guys', I would have lent you something to wear." We kept teasing back and forth, with me saying that that wouldn't
have worked, and her insisting that it would have. "We're really almost the same size, Bobby, I'm sure that I could have found some things that would have fit you."
"Don't be ridiculous," I said, "women's clothes wouldn't fit me, and I'd be willing to bet on it.
She looked at me a little strangely, and said, "I'm willing to put my money, or rather the company's money, where my mouth is. I know you're due for a raise next month, and I was getting ready to fill out the form for a $3,000 increase. But I'll bet you, two-to-one, that I'm right."
She outlined the terms of her proposed bet: She'd give me a $4,000 raise if I were right, and only $2,500 if she was wrong. To tell you the truth, I'd only been expecting about $2,000 or so, since I'd heard raises weren't going to be that great, and we were both pretty high, I guess, because I heard myself saying, "I'll take that bet." She giggled a little, and said she'd be right back. Before I had a chance to reconsider, she was back with an armful of her things, and she handed them to
me.
"Here you go," she said, "go in and change, while I think about the money I'll be saving the company."
"Better think about how you're going to explain that big a raise, Wendy," I responded, "because I still think I'm right." I went into my bedroom, and laid the bundle on the bed. I quickly stripped off my clothes, and picked up the lace-trimmed pink satin panties from the bed.
"Oh, boy," I thought to myself, "a $4,000 raise," fully expecting that I'd win the bet. I sat down and pulled the pink panties up over my legs, and my first thought was that I was in trouble - they were very stretchy. When I stood up, and pulled them all the way up, they easily covered me. But the feel of the satin against my cock, so unlike my regular jockey shorts, soon had my thoughts
going in a different direction, or rather erection. The smooth feeling, together with the realization that I was wearing Wendy's panties, and my fantasies from the plane mingled and merged.
"This is ridiculous," I thought, though I was less sure of winning the bet now. I put my arms through the bra straps, and struggled to hook it closed behind me. It, too, was very stretchy, and fit easily around me. I sat down again to put on the black pantyhose, remembering how my girlfriends had done it, hoping that this would be the thing that wouldn't fit. But unfortunately, they did, and I stood up in my matching bra and panties, with the pantyhose securely around my waist. All thoughts of the bet were nearly gone as I felt the sheer garments caressing my body. This was an economic-erotic nightmare!
The pantyhose were control top, and I felt them compressing my body. I slipped on the blouse over my flat, but bra-clad chest, and felt the silky feeling spread all over my upper body, matching the feelings that the panties and hose were giving my lower body. The buttons were on the 'wrong' side, of course, but they did fasten the blouse around my chest. All that was left was
the straight black skirt, which I slid over the pantyhose, and zipped up on the side, and the black patent leather high heels. I thought that the shoes would be too small, and they seemed to be,
when I heard Wendy enter the room.
"Well, was I right?" she asked. "I .. I don't think the shoes fit," I stammered, but she knelt down in front of me, and pushed them onto my feet. The smooth nylon of the hose slid my feet into them, and rising up, Wendy took my hand and helped me stand up. It was precarious, being perched on top of the heels, and even more so as she led me to the mirror, my steps small and mincing from the arch of the shoes and the tight fitting skirt.
"See, I was right!" she said, disappearing for a minute into the bathroom, and returning with a handful of tissues. "As a matter of fact, there's even room for these," she said, opening the front of my blouse and stuffing the tissues inside the cups of my bra. She rebuttoned my blouse, and we looked at my strange reflection in the mirror. From the neck down, I looked just like a woman. Except for the bulge at my groin, where my cock, I thought clearly showed its excited state. She either didn't notice it, though, or ignored it. Only my male face, and my man's haircut betrayed the fact that I wasn't a woman. "I just knew it," she said, gloating a bit over her victory. "I'm just sorry that I didn't make the bet I originally wanted to offer."
"And what was that?" I asked. She moved a little bit, and almost lost her balance, showing the effects of the wine and the drink.
"I almost was going to say that not only would my clothes fit, but that I would bet that I could totally make you pass as a woman," she replied. "In fact, to show you what a sport I am, I will make that bet, if you want - double or nothing again."
I quickly thought to myself, there's no way I would ever pass for a girl with my short hair, and without thinking of the consequences, I answered, "I'll take that bet. $3,500 if I win, and $2,000 if I lose."
"You've got it," she said, leading me into her bedroom, and sitting me down in front of the dressing table. She started applying a cream foundation on my face and for the next few
minutes, I could see and feel her concentrating on the rest of the makeup. She even glued false eyelashes and nails on me, and when she stepped away from the mirror, my heart sank for a
moment. So skillfully had she applied the makeup, including a bright red creamy lipstick, that the face that stared back at me was clearly feminine. Now only my short hair remained as testimony to my manhood - that and my now-raging hard-on which threatened to burst through my panties.
Wendy disappeared for a minute, and then returned holding something behind her back. "Thought that your hair would win the bet for you, Bobby?" she asked, taking a curly wig out of hiding, and placing it on my head. I had closed my eyes while she did this, and when I opened them again; a beautiful woman was staring back from the mirror. This was too much, I thought. She really did it, there was no way to tell there was a man underneath the clothes and makeup, and I realized that I had lost the second bet as well. She walked me over to the full-length mirror, and as she did, the feel of the soft silky clothes against my body, and my memory of the feminine face I now had inflamed me still further. My cock bulged against the tight skirt, now clearly visible. Wendy stood next to me, and focused her eyes on its reflected image. "You really are turned on by this, aren't you, Bobby?"
I felt color rushing to my face, and even though I couldn't explain why it was so, I shyly said, "Y...yes, Wendy, it does."
She grasped my cock through my skirt, and then, startling me, called out, "Come on in, he's ready!" Before I could react, I heard someone come into the room and say, "You've outdone
yourself this time, Wendy, she's gorgeous!" I turned quickly, almost falling because of my high heels. Standing in the doorway was a petite blonde, looking at me with an amused expression on
her face. She walked over toward me, and I could feel my face turning beet-red over the embarrassment of being seen like this.
I stuttered out, "W...Wendy, who is this - what are you doing to me?"
She said, "Bobbie, I'd like you to meet my friend Marsha. We go back a long way together, and one of the things we've always loved is to dress up guys in women's clothes." A sudden flash of light exploded in my face as Marsha took a picture of me with a camera she had concealed behind her back when she came into the room.
"Hi, Bobbie, so nice to meet you," the blonde said. "Don't be angry at our little game," she continued, "I think you'll find that there are substantial benefits to playing with us, right Wendy?" Wendy's hand had not moved from my cock, and Marsha walked over and placed her hand on my silken-covered buns. Instead of answering, Wendy turned to me and gave me a long passionate kiss, squeezing my cock in its satin prison. My mind was a jumble of thoughts, not knowing what was happening to me. While Wendy continued to kiss me, Marsha bent down in front of me, lifted my skirt, and freed my cock from under the pantyhose and panties. Another bright flash, and I knew that the sight of my cock, surrounded by satin and nylon, had been captured.
Before I could think about that though, I felt her lips kissing the head of my engorged cock, then sliding down the shaft, engulfing me. The excitement I had felt from the touch of satin was heightened by this, and in just a moment, I felt myself shooting cum deep down her throat.
Wendy began unbuttoning my blouse, and then unzipped my skirt. I stood there in lingerie and heels, recovering from my orgasm. Both of them began to strip off their clothes, and in another moment, I had my first look at their magnificent bodies. "Just let us do the work, Bobbie," Wendy said to me, as they each took a hand and led me to the bed. I had never been in a three-way orgy before, but clearly they had. My feminine-clad body became the sole focus of their attention, and they kissed and caressed me for a while, bringing me back to an excited state. Wendy climbed on top of me, and impaled herself on my again-erect cock. Marsha moved up on the bed, and then swung her leg across my head. Her pussy was hovering just above my lipstick
covered mouth, and not only couldn't I ignore it, I wanted to eat her until she screamed. I didn't care what was going to happen any time in the future, not right then; all I wanted was to experience the moment. She lowered herself onto my mouth, and I began to lick and suck on her clit, probing deep inside her with my tongue.
The two of them leaned together and kissed, while their hands were busy stroking each other and me. In no more than a minute or two, both of them began to gasp and shudder as they orgasmed together. I hadn't come again, and after pausing to savor their orgasms for a few seconds, they scrambled to switch positions on my body like a well-rehearsed team. I tasted the different, but delicious juices of Wendy's pussy while Marsha proceeded to milk me dry with her well-lubricated sweetness. I felt myself ready to cum again, and first Wendy, then Marsha, joined me in a near simultaneous explosion.
"Dear, sweet Bobbie," Wendy said to me a few minutes later, as I lay, still feminized between their two naked bodies, "I'm sorry I had to trick you like this. But I could just visualize how you
would look as a woman, and as I'm sure you've guessed, making love to feminized men is a special turn-on for Marsha and me. Somehow, though, I seem to think you didn't mind it all that
much, did you?"
I thought for a second, and then replied, "No, of course making love with the two of you was fantastic, but being dressed like this, I... I just don't know..."
"Come on, Bobbie," she said, "I saw how hard you were under your skirt, inside your pretty pink panties. Don't try to tell me that you didn't find wearing women's clothes a turn-on." I could feel
myself blushing beneath my makeup. She was absolutely right, of course; although my head had tried to deny it, from the first moment I felt her panties on my cock, I was hooked. "Do you really think I was, am, pretty?" I shyly asked, abandoning all pretenses that she was wrong in her judgment of my newly discovered TV inclinations.
"You really do make a pretty girl, Bobbie," Marsha chimed in, "I couldn't wait to suck on your she-male cock, or to feel it inside me. I'm sorry, too, for tricking you. But I hope that this won't
be the end of this for us?"
"N...no, I don't think so," I said immediately. "I...I can't explain why something I never even thought of before, wearing women's clothes turned me on so much, but no, its definitely something I think I want more of."
"How much more, Bobbie," asked Wendy, "have you given that any thought?"
"No, I haven't," I replied, "this has all been happening so fast, but I know that I want more experiences like tonight's. It was wonderful." With that, they both started kissing me again, and I
found myself getting excited again. In a few minutes, Marsha was laying down on the bed, being eaten by Wendy, who was on all fours between her legs. I was standing at the foot of the bed,
perched on my high heels, pumping my cock inside Wendy's exposed pussy. I was almost ready to cum, when Wendy reached back and gave my cock a hard squeeze, preventing my orgasm. They quickly switched positions, and I started to slide my cock inside Marsha's wet hole, when she repositioned me to enter her ass. My well-lubricated shaft hesitated at the tiny, puckered entrance, and then slid inside as she thrust her hips back toward me.
Her ass was tight around me, and when I picked up the rhythm, I came inside her with a final spasming thrust. I leaned forward on her body, and she lay on top of Wendy, her mouth bringing another giant orgasm to the tall brunette. We stayed in a layered heap for a few minutes, recovering, and then the girls helped me out of my things. I parted with them reluctantly, not wanting to lose the feeling of the panties and other silky things against me, but we then all crowded into the shower stall, in a warm, loving jumble of glistening naked bodies.
My mind was distracted as we dried each other off, thinking about the weird, but wonderful, events of the night. Practical considerations began to intrude on my thoughts, thoughts like the
fact that they had taken my picture, that Wendy was still my boss, and that my raise had been cut substantially as a result of losing the bets. Where was my newly discovered TV tendency going to lead? I didn't know any of the answers to these questions, as the girls helped me into a silky white peignoir set, then put on their own nightgowns. There didn't seem to be an appropriate time to raise these issues, as we crawled into the king-sized bed, the girls making sure that I was sandwiched between them. They each kissed me goodnight, and then kissed each other, when Wendy said, "Bobbie, there are a lot of things we have to talk about, but I think the morning would be best, don't you? I know I'm exhausted, and I'm sure you are also." I admitted I was, and we all said goodnight. But tired as I was, I found myself unable to fall asleep immediately; thrilled by the feeling the silky nightie was giving me. I lay there quietly, so I wouldn't disturb them, until my jumbled mind finally gave up and I fell into a deep, dreamless sleep.
Or at least I thought it was dreamless, until early the next morning I woke up to the gentle caresses of four hands roaming all over my silken-clad body. It seemed as though I was not the
only one who must have had some erotic dreams during the night. My cock was fully erect, and the girls were paying it particular attention. I was lost for a moment until the memories of last night's activities flooded back to me. When they saw I was awake, there was a moment or two of giggling, and a great flurry of activity as our three nightgowned bodies maneuvered around. Marsha's sweet pussy was again just above my lips, and her gown swirled around my head. This drove me wild as the sensation of the smooth silk around my face matched the feeling of the nightgown around the rest of me. Marsha took me into her mouth, and Wendy assisted with deft licks and sucks on my balls. When I had brought Marsha to orgasm with my tongue, the two of them again switched positions, and I tasted Wendy's different, but still delicious nether lips against my tongue. Wendy and I came at the same moment, and I felt a mouth, drink it every drop of my spurting essence.
After a while, Wendy called down for room service, and about fifteen minutes later, the three of us were sitting around the table, all still our nighties. The girls had slippers on, but I had slid back into the high heeled pumps I had worn last night. I felt a little strange, sitting there, in my short hair and unmade-up face, but I didn't say anything about it.
When we had had a cup of coffee and some juice, before we began to dig into the rest of the breakfast, Wendy began to speak. "Bobbie, I know how confusing all this seems to you, and I'd like to explain a little. As I told you last night, Marsha and I have been friends for a long time, and I guess you could tell, you're not the first man who we've shared our love with. It's surprisingly easy to get a man into a feminized state, as you found out last night." I could feel myself blushing at the realization of how easily I had been tricked. She continued, "Sometimes, there are regrets the next morning, and that's basically the end of it, just a one-night fling. But,
occasionally, there have been some men, and I think, and hope, that you're one of them, who have loved to have the feminine side of them exposed, and they've wanted to continue to explore the fantasy. I just want to tell you, though, that no matter what, you shouldn't feel under any pressure or obligation because we work together. I always keep my business life and my personal
life strictly separate. Oh, by the way, those picture that we took are for a private scrapbook we keep, not for any other purpose." We started to eat, while I considered the things she had said. The two of them chatted together about different things, giving me the opportunity to think for a while.
Finally, I thought I had sorted out my feelings a little, and I spoke, "While it was a kind of dirty trick you two played on me last night, I can't deny how fantastic I felt. And though I don't know where this may all be headed, I definitely know that you've turned me on to something I know I don't want to give up, at least for a while. I can't make any promises about the ultimate outcome, but I'd love to continue with it for a while."
They got up and came over and hugged me. "I'm glad you feel that way, Bobbie, and I know Marsha is, too," Wendy said. "I think we'll have a great time together on the journey. But, unfortunately, it's almost time to get downstairs for the opening session, and I don't think you want to go there dressed like that!" We all laughed, and we separated to being dressing for the
conference.
I went back into the other bedroom, and began to put on my things. The suit I was going to wear would be all right, I thought, but I hesitated when I had pulled my jockey shorts on. The feel of the cotton, which had always seemed so comfortable before, was rough against my well-used cock. Or maybe that was my imagination, and the problem was just that I loved the feel of satin panties more instead. Without even thinking twice, I walked naked into the other bedroom where the girls were now dressing. They were in their underwear already, and dissolved into laughter when I asked if they had a pair of panties I could wear under my suit, "since it seems that I'm a bit sore from last night."
Wendy stopped laughing long enough to dig out the satin pair I had worn the night before, and tossed them to me. "Here you go, Bobbie, sorry that we made you so sore," she giggled, and almost as an afterthought, I bent down and picked up my used pantyhose. "I think it may be a bit chilly - maybe I should wear these, too," I teasingly suggested, and I left the room, all of
us laughing heartily.
The panties and hose felt as wonderful this morning as they had last night, and I quickly put on the rest of my clothes over them. We went downstairs, and I was glad that my suit jacket hid my cock, which had responded to the smooth silky undies I wore. The morning's session dragged on interminably, and I sat there with the panties exciting me all morning. We decided to skip the opening luncheon, and when we got back to the suite, the girls took pity on my plight. They pulled off my suit pants, and, kneeling down in front of me, gave me the most tremendous blowjob I'd ever had, licking and sucking me until Marsha pulled me deep inside her, until I shot a torrent down her throat.
While I recovered, and Marsha went into the bathroom to clean up, Wendy asked me if I'd like to take the afternoon off to go shopping. Now normally, I hate to shop, but I had the feeling that we wouldn't be looking through too many male things today. She confirmed this, saying as Marsha returned, "I'm going to run out of panties if I have to share them for a week, Bobbie - would you like to pick up some of your own? Oh, by the way, you can forget about losing the bets last night, that was only a pretext." I could feel myself blushing again, but the thought of having my own feminine things to wear was exciting. I agreed, and thanked her for letting me off the hook for the losing bets.
"That's OK, Bobbie," she said, laughing, "because I think you're going to need the money, for your new wardrobe."
As we walked out of the hotel, Wendy filled me in about Marsha. I learned that she worked for one of our competitors, in the equivalent of Wendy's position. They had met while on a training
program at another firm after they had graduated from college, and during their first year of working together, had discovered their mutual interests and established a relationship. They continued working together for another few years, and after getting some solid experience under their belts, had left to join their new firms. The talk quickly switched off that topic, however, as we went into the department store that was up the street from the hotel. They led me into the woman's department, and for the first time, it was difficult for me to try to maintain the typical bored male's attitude toward his wife/girlfriend's shopping, since I knew that everything they
picked out was really for me.
They began in the lingerie department, where they selected several pairs of panties and pantyhose, and some nightgowns, asking me for my approval on each. I was thrilled by the very
thought of wearing these things, and could do little more than dumbly nod `yes' to each. Then turned to more exotic items. I didn't even know the names of some of their selections, but they
whispered to me that they were designed to give me extra shaping. Wendy paid for these things, telling me that today's shopping trip was on her and Marsha, to make up for the trick they had played on me.
Next stop was in the dress department, where they chose a couple of daytime dresses, before looking at the fancier party dresses. They ooh-ed and aah-ed over them, while I managed to seem unconcerned, though I began to picture myself in each one as they held it up for approval. They finally decided on a royal blue sheath gown, and as Wendy paid for the selections, Marsha whispered that she was getting all wet, thinking about it on me.
We left the store, and Wendy commented on my control, and how I'd maintained the bored attitude of a typical guy. "Let me tell you," I said, "it was hard - in more ways than one!" We walked a little further and went into a Payless Shoe store.
"This place is great," Marsha said. "There aren't a million clerks hanging over you, and you just pick your shoes off a shelf." The store was pretty empty, and as she had said, we walked right back to the women's shoe area unchallenged.
My brain did a flip as I saw the rows of high heels, and after quickly checking one pair on for size, my heart pumping with the possibility of being discovered, they chose three pairs of shoes
to match the dresses they had bought for me. We brought the shoes up front and paid for them. "God, I was worried someone would see me," I admitted.
Marsha said, "Hey, don't worry, this is San Francisco, after all. I'm sure that even if someone did spot you, it wouldn't have fazed them a bit."
We walked a little further, and before we went into a wig shop, they asked me if I had any preference about color. "Well," I thought out loud, "you're a brunette, Wendy, and you're a blonde, Marsha - I guess that leaves being a redhead to me, doesn't it?" They talked for a minute, agreeing that color would suit my fair skin, and the things they had bought me, and in just a few
minutes we walked out with two wigs, one in a shoulder length, straight cut, and the other in a longer, curly style. After two more quick stops for cosmetics and some costume jewelry, we headed back to the hotel. It was just mid-afternoon, and we had decided to blow off the sessions for the rest of the day.
The elevator, which had seemed reasonably quick before, now seemed to be an endless trip, because I wanted to try on some of my new things so much. We no sooner got into the suite than they attacked me, almost ripping off my suit, tie and shirt. My clothes were discarded onto the floor, and they led me into my bedroom. We talked for a minute about what to try on first, and
they outvoted my suggestion of the party dress, saying I should work my way up to that. I stripped off my borrowed panties and hose, and held a white torsolette against me while they fastened the hook-and-eyes.
I felt myself being squeezed into a feminine shape by the deceptively strong lacy garment. It pulled in my waist quite a bit, while pushing my flesh upwards into the padded bra cups. Even though I knew that most of my bust was from the padding, I saw that the torsolette gave me my own little titties. There were four long garters hanging from the bottom of the torsolette, and they sat me down on the side of the bed, showing me the proper technique for rolling the sheer nylons up over my calves and thighs. They fastened the garters on, and then Marsha held a pair of panties for me to step into. "Your first pair of panties of your very own, Bobbie," Wendy said, causing my already erect cock to twitch. "That will never do, Bobbie," Wendy said, eyeing my male protrusion, and she lowered her lips around me, bringing me to a quick climax. The panties now fit with no telltale bulge, as Marsha reached in and tucked me back.
The afternoon passed quickly, as I tried on all the things they had bought me. After I had put on the first dress, they applied a full makeup to my face, and put the straight wig on my head. Once I had been totally transformed, the time was like a dream, as I watched and felt my feminized self changing from one thing to another. They hadn't changed my undies as I went through the daytime things, but when the only dress I hadn't worn was the blue cocktail dress, they removed the white outfit, leaving me entirely naked. Wendy got out a set of black underthings, and I
stood still as they laced me I into a waist cincher that pulled in my body by at least six inches.
"I can't breathe," I gasped out, and they laughingly told me that all girls had to suffer at least a little for fashion. I could barely sit as they pulled on sheer black nylons and attached the garters to hold them up. Frilly black panties followed, and finally a strapless black bra, that was underwired and padded. The tops of my new breasts were pushed up over the top of the bra, giving me the impression of real cleavage.
They walked me over to the full-length mirror, and I saw just how much they had been able to transform me. I noted that I would have to shave the few hairs I had on my chest, and my legs, of course, and I was startled to find myself thinking this way. I said this out loud, and both of them stared at me for a minute. "Do you mean you'd be willing to shave yourself all over, Bobbie?" Wendy asked, and when I said that I would, I found myself being led into the bathroom. The next thing I knew, my stockings had been rolled down, and the two of them were lathering me up. The hair from my legs, chest and underarms disappeared under their careful ministrations, and they lovingly used a washcloth to remove the remnants of the lather.
We went back into the bedroom, and I felt the even more intense sensations of the stockings being put back on. Aside from the smooth sleek feel of them on my legs, my sensitivity was heightened by the shaving process. I rubbed my stockinged legs together, delighting in how they felt. Marsha put my new royal blue heels in front of me, and I stepped up into them with their assistance. They fit so much better than last night's heels, and although they were obviously women's shoes, they just seemed to mold themselves around my stockinged feet.
I walked, somewhat precariously, across the room and stood in front of the mirror. Marsha replaced the straight-cut wig with the curly one and then Wendy lifted the dress over my head. I raised my arms so it would slip down over me. It had a sweetheart neckline, which showed off my new titties, and the top was of a gauzy material that covered not only the top of my body, but extended down my arms. The impression was so exciting to both the touch and the eye: the silky feel of the ultra-feminine clothes on my body, and the seemingly modest but very sexy look of the sheer material over the almost daring lower dress. I felt tears coming to my eyes, as I was so moved by my transformation, and they each put an arm around my waist, standing on either side of me.
The reflection I saw was clearly that of a young woman, and the last vestiges of my manhood seemed to melt away, as my mind made the transition into femininity as well. From the curly hair to the toes of my high-heeled shoes that just peeked out beneath the hem of the full-length sheath dress, there could have been no doubt that what anyone who might have seen me would have thought- that this was truly a beautiful woman.
I burst out into tears, startling both of them, and I quickly answered their unspoken questions with, "No, don't worry, I'm not upset - its just that I... I'm s...so h...happy!"
They hugged me close, and comforted me, and Wendy said, "I'll bet you never cried because you were happy before, did you, Bobbie?" I shook my head `no' as the tears continued to roll down my face. When I regained my composure, they fixed my makeup, and I spent the rest of the afternoon, practicing my newfound feminine persona, walking around in the snugly fitting dress on my new heels. Everything about the time was fascinating, and the girls spent much of the time tutoring me on little feminine traits, how to walk and sit properly, etc. They told me later how well I took to this new role, how my maleness seemed to disappear, to be replaced with what was at first an awkward, then a surer femininess. They were super-complimentary, reassuring me of how pretty I looked, and how quickly I made improvements in myself.
To tell the truth, I felt very natural, almost from the first, and they kept me so busy that I really nearly forgot what an incredible erotic experience wearing women's clothes was for me. They made me change out of the evening gown, and made sure that I became comfortable with the other things they had bought me. I did resist changing out of the black underwear, when they suggested it, though, and Wendy teased me that I liked the sexy, slutty way it made me feel. And she was right! Even in the most ordinary daytime dress, just knowing that I was wearing the black frillies made me feel sexy.
As it grew toward evening, Marsha said, "I don't know about you girls," sending a thrill through me hearing myself referred to that way, "but we skipped lunch and I'm starving. Do you want to
go out," she teased me, "or order something from room service." We quickly decided on room service, and, as I reflected on the afternoon's activities, my sexual arousal grew. I became aware of the fact that the afternoon had turned Wendy and Marsha on as well, and we indulged in a little kissing and petting until we heard the knock on the door.
They had become much more disheveled than I had during the course of the afternoon, but I recoiled with horror at Wendy's suggestion that I answer the door. "I can't let anyone see me like this," I whispered back at her.
"Sure you can, the guy won't even blink, except maybe to stare at how gorgeous you are." I wasn't sure at all, but when the two of them ran inside and disappeared, I screwed up my courage, and
opened the door, silently cursing the girls to myself for having left me in this position. But as the bellboy set the dinners on the table, and I signed the check, using Wendy's name to cover my femme self, I didn't notice any reaction on his part.
When I added a generous tip, he merely said, "Thank you, Ma'am, and have a good evening."
After he left, I stormed into the bedroom where Wendy and Marsha had fled, and found them giggling uncontrollably. My anger dissipated immediately, seeing them, and I joined in their laughter. "That was really awful of you two," I managed to get out, "I almost peed my pants at the thought of facing him, dressed like this!"
As we sat down, Wendy said, "I'm sorry again, that we did that, but we knew that you could easily pass as a woman. No matter how many times we told you that, though, you would never have believed it until you had proof for yourself, and now you do."
"I guess you're right," I answered slowly, "and they say that the best way to learn to swim is to get thrown into the water, but I still almost had a heart attack." When we finished dinner, and the bottle of wine we had ordered, I gathered everything up and left the tray in the hall. I was excited again, and I knew that they were, too. They practically carried me into the bedroom, and they unbuttoned my dress and removed it. Wendy bent down and pulled off my panties, leaving me in the black torsolette, stockings and heels. Marsha opened the bag with the nightgowns they had bought me, which I really hadn't noticed when we were shopping.
"Do you feel a little risque, Bobbie?" she asked, pulling out a black and white garment. Without waiting for an answer, she tossed it to me, and when I held it up in front of me, I saw it was a short nightie that looked like a maid's outfit. It was of black nylon, with a tiny attached apron, and I knew it would go perfectly with the black frillies I was wearing. I raised it over my head and slipped it on. It had long sleeves, ending in white lacy cuffs, and the hem of the micro mini-skirt was also trimmed in white lace. The neckline was low-cut, exposing the tops of my smooth creamy breasts. Wendy placed a black velvet choker around my neck, and as she moved around me, I felt the gentle movement of air against my exposed cock. The skirt just barely reached the tops of my stockings, and hid my erection.
I stood there just looking at the fantasy woman in the mirror, not noticing what the girls were doing. In a minute or two, they stood next to me, each in black outfits that resembled the torsolette I was wearing, with black stockings and extra-high black heels. Psychologically, I felt dominated by the two of them, dressed as a servant in my maid's outfit. Wendy held a nylon stocking in her hand, and she took the lead, bending down to tie the stocking around my cock.
She led me by pulling the stocking, and forced me to my knees in front of her. "Would you like to eat my pussy, Bobbie?" she asked, and without answering, I quickly leaned into her crotch and began to lick on her exposed cunt. She pulled my head closer, and she came almost immediately, her sweet juices running down my face. She handed the stocking to Marsha, and Wendy's sweetness was replaced by Marsha's. I serviced her as well, my own cock throbbing from my activities and the touch of the stocking.
When I raised my head from Marsha's pussy, I saw what Wendy had been doing when I was busy with Marsha. She had put on a harness-like device, and inserted one end of a small, double-sided dildo into herself. "Suck my cock, Bobbie," she breathed, and I began to lick the tip of the rubber cock. She let me do that for a moment, then led me over to the bed, where she lay down, pulling me into a kneeling position in front of her legs. I resumed my efforts on the false cock, not realizing or caring that my skirt rode up on my ass. As I worked on her cock, twisting and rotating it inside her, I felt Marsha behind me. She stroked my cock, playing with me, and then I felt her finger touching my tiny, puckered asshole. She must have used something to lubricate it, because she was soon inserting her fingertip inside me, first, just the tip, then the entire length of her finger. I found myself responding to her penetration, moving my hips back and forth in rhythm with her motions. A second finger joined the first inside me, as I relaxed myself to her.
From around the false cock which filled my mouth, I moaned, "Oh, yes, give it to me," as she finger-fucked my virgin butt-hole. Wendy pulled me closer as my sucking and twisting of the dildo brought her off in a gasping, heaving orgasm, then released me. They quickly exchanged positions, and I found my face buried deeply in Marsha's pussy, licking at her clit. Wendy moved around behind me, and the emptiness of my ass was filled as she inserted one of her fingers, moistened with her cum juice inside me. She probed me deeply and I again began to moan, rising
in pitch as her second, then third fingers probed inside me.
Marsha's legs wrapped themselves around my head, pinning me against her pussy, when I felt Wendy withdrawing from me. Her fingers were replaced at the entrance to my virgin ass by the tip of the dildo, and I realized what was about to happen. The thought frightened me, and I tried to resist from fear, but she leaned over and whispered to me, "Trust me, Bobbie, I'll be gentle." She inserted the tip of the false cock into me, and then waited as my fear subsided and my hole relaxed around the dildo.
Marsha regained my attention as she writhed around under my mouth, and the anal invader slowly made its lubricated way inside me. Suddenly, my relaxation was total, and the full length of the shaft slid into me, filling me as never before. The sensation was strange, but after the probing of the tiny, feminine fingers, wonderfully filling. I found myself thrusting back to meet
Wendy's slow rhythm, and moaned, "Yes, yes, fuck me!"
As Wendy picked up the pace, ramming her cock into me, her hand reached around me and grasped my cock, stroking it with her cum-juice slick hand. I gave into the twin sensations, as her
hand and cock moved together, and with a final backward thrust, my cum shot out in great spurting gushes, as I felt Marsha come simultaneously. I collapsed on top of Marsha, totally spent and exhausted, but when I felt Wendy starting to withdraw from between my ass-cheeks, I managed to raise one hand to hold her against me. I could not speak because my mouth was still locked and buried in Marsha's pussy, but I had grown used to the filled feeling, and didn't want to experience the emptiness just yet.
Wendy lay on top of me, and both of their hands were stroking my body and head, and I felt so contented that I almost began to drift off to sleep. Finally though, Marsha who was bearing the weight of both of us, said that she needed to breathe, and I reluctantly moved my body off to the side, turning so that I was facing her. I had twisted Wendy around with me, so that we lay like spoons, her cock still buried deep within my ass. She gave me tiny kisses on the back of my neck, as Marsha kissed me deeply on the lips, both of them hugging me against their bodies. I was the first one to speak, the first words other than my impassioned pleadings while we were making love. "A little risque, Marsha, that was a little risque?" Both of them laughed, Wendy's movement shifting the still rigid cock inside me.
"I guess that might have been an understatement, Bobbie," Marsha said.
We lay there, silent again for a while, and I thought about what had taken place in just 24 hours. My entire world had been turned upside down: I would have told anyone who said that I would be totally feminized, with a dildo fucking my ass, that he was crazy, but here I was. Not only that, but I knew that I loved what had been done to me, and that far from an aberration, this was something I wanted more of. Although they continued to hold and cuddle me, the girls were silent, realizing, I guess, what was going through my mind. As different and strange as this
experience had been for me, I knew that they had opened up their relationship to an outsider, maybe not for the first time, but still leaving themselves exposed and vulnerable as well.
"Any regrets, Bobbie?" Wendy ventured, giving me the opening to share my thoughts with them.
I thought for a minute, and as I looked deeply into Marsha's eyes, I responded, "Yes, Wendy, I think I do have one regret." I felt Wendy sag against me a little, and I saw the slightest tinge of uncertainty on Marsha's face. I couldn't contain my amusement, as I said, "I think that I'm a little disappointed - but only that Wendy doesn't have a bigger cock!" I saw that I still had much to learn about the female perspective, as they tried to grin, and then dissolved in tears. I worried for a moment that I had really upset them, but then realized that they were tears of happiness, and that they had taken my comment as the joke I had intended.
When we woke the next morning, it was pretty frantic, since we had fallen asleep pretty much the same way, all of us being totally exhausted. The girls helped me take off my makeup, and then we each hurriedly showered. I didn't hesitate a second to pull on a pair of panties and pantyhose, my own this time, under my suit. I got the same warm tingling feeling from their touch on me, reassuring me that the thoughts I had had last night were still the same in the light of day. We attended the day's sessions diligently, and had another rousing dress-up and lovemaking session afterward. The next three days followed the same pattern, and we spent lots of time circulating among the other attendees, networking and building up our contacts. Finally, it was the last day of the conference, culminating in a fancy dinner-dance.
"I wish I could wear my party dress, instead of this suit," I complained to the girls that afternoon. "I would love to be `out' even if no one knew it." Wendy and Marsha looked at me strangely, since I had resisted all their pleadings for the last few days to venture out while Dressed.
"Are you serious, Bobbie?" Wendy asked me. "Would you really consider going to the dinner dressed?"
"I...I think I am, Wendy." Marsha and Wendy looked at each other, and started discussing it. I had never attended one of these conferences before, so I didn't know what the dinner-dance was like, but they had been to several. "You know, Marsha, there are a couple of hundred people there, and after the two-hour cocktail reception, everyone is pretty blitzed. I guess the biggest
problem would be the people they've assigned to our table. If they've met Bobbie, that would pretty much rule it out."
"You're right, but if they hadn't met him, ...they could meet her! Is there any way of finding out who our tablemates are beforehand?" Wendy picked up the phone, and called down to the conference center, and found out that they had put together a patchwork table for us, six people from Idaho, and a seventh from South Dakota. We talked about whether or not any of them had met us, and found out that they hadn't. As a matter of fact, no one even remembered seeing anyone from either of those two states. "I'll bet they blew off every session, and spent the whole week sightseeing and goofing off, here in the big city," Wendy said.
"Well, that pretty much settles it," I said, "at least as far as I'm concerned. If we skip most of the cocktail party, no one at our table should be able to even see by dinnertime."
"Bobbie, are you sure about this?" Wendy asked. "I mean, I know that dressing turns you on, and you've really learned a lot about how to act properly in the last few days, but this is a big step. I...I'm a little worried, to tell you the truth."
"I know it seems like a spur of the moment thing," I said, "but let's face it, only you manager types get any real attention at this thing. We peons who are brought along for the ride, as a perk, just fade into the background, anyway. I'll bet at this whole conference there are only 5 or 6 people who'd even remember my name. I just think it would be a real kick, and I'd really like to do it." The girls debated for a minute, then giggling, decided why not?
They treated me like two older sisters, getting their younger sister ready for the prom. The thought of being out among other people while dressed was a little frightening, but it was more exciting. They gave me a bubble bath, and shaved me very carefully, all over. My cock was standing straight up when they started getting me dressed, but the two of them took care of that pretty quickly.
"Bobbie, I think we're going to have to do something about this," said Marsha, holding my now-limp cock. Wendy went over to her dresser for a minute, and returned holding a pair of control briefs. "If you tuck yourself back inside these, I can guarantee that nothing will show. They're tight on me - I don't even know why I even packed them - but now I'm glad I did."
I stepped into them, and struggled to pull them up. They were really tight, but with my cock tucked back, all that you could see from the front was a realistic mound that looked like a woman's pussy. They fitted my black torsolette around me and fastened it up tight, padding the cups below my raised chest flesh and making my breasts rise above the cup tops.
I moved over and sat on the bed, as they attached my stockings to the hanging garters, then stood up and raised a pair of silky black panties into place. I stepped into the royal blue high-heels, and they lifted the dress over my head and zipped me up. Wendy had been right - the control panties held me firmly in place, and nothing showed at the front of the sheath dress. They led me over to the dressing table, and placing a towel around my shoulders, proceeded to put on a full makeup, including the longest, fullest eyelashes I had ever seen, courtesy of Marsha.
They put the long, curly wig on me, brushing it carefully, so that it looked like I had just gotten out of the beauty parlor. While I waited for the nail tips they had glued on to dry, they got themselves ready. They had finished putting on their gowns and makeup, and had applied a deep red polish to my nails, matching the color that covered my lips. I began to laugh, and Marsha asked me what was so funny.
"We are," I managed to say, "we look like a flag for God's sake!" They saw what I'd meant:
Wendy was wearing a sexy red dress that complimented her brunette hair, and the radiant blonde Marsha wore a white gown that showed off her petite, sexy figure to perfection. They joined my
laughter, but there wasn't anything we could do about it, since these were the only formals we had.
We walked over to the mirror and checked out our appearance. "Well, we may look like a flag," Wendy said, "but I can guarantee that more than hands will be saluting us tonight. Girls, you both look gorgeous." I beamed with pride, and we returned her compliment.
We checked the time, and saw that the cocktails had been going on for more than an hour and a half, so it was time to go. As we walked out of the suite toward the elevator, they kept up a steady stream of last minute instructions and word of advice for me. It took my mind off my nervousness, I guess, because I felt pretty calm, much more so than I would have expected. When we got to the ballroom, the noise level confirmed our suspicions that plenty of alcohol had been flowing, and no one noticed us when we walked in. "Remember to try to pitch your voice properly, Bobbie.
"And talk as little as possible," Wendy said as a final warning.
We went over to one of the bars, and Marsha ordered drinks for us. None of us wanted to get tipsy, of course, but we would be out of place without one in our hands. We chatted among ourselves for a few minutes, and as I looked around, I noticed that we were attracting quite a few serious looks from the men standing around the room. I mentioned that to Wendy in a whisper, but she replied, "what do you expect - let's face it we are three pretty attractive women, and men are going to stare at us."
"Are you sure that they haven't figured out about me?" I asked.
"No way, Bobbie, believe me, there's nothing but pure lust in those eyes!" I guessed that she was right; I didn't see anything strange in the way they were looking at us. In a few minutes, the lights dimmed, then went bright again, signaling that we should get to our table for dinner. We were the first to sit down, and the girls shielded me by sitting on either side of me. The rest of our table, all men, got there soon after, and as we had speculated, none of us recognized any of them. I felt fairly comfortable, and the sound of the band and the noise in the room were so loud that conversation with anyone not sitting next to you was almost impossible.
We ate our appetizers and salad, and then there was a short break before the main course. The band was playing dance music, though, and before I knew what was happening, three of the men got up and asked us to dance. I hesitated, but didn't have much choice since the guy who had asked me was pretty drunk already, and I didn't want to make a scene. He led me to the dance floor, and I felt my knees shaking as he put his arm around me and pulled me close to him. I was having enough trouble dancing in my high heels, when I realized that he was grinding his groin up against me. Horny Bastard, I thought, and I pulled myself back as much as I could.
I was relieved when the dance was over, and I could return to the table and sit down. "That S-O-B was dry-humping me," I complained to Wendy.
But she just laughed and said, "What do you expect - as far as he can tell, you're just a fantastic looking woman, sweetie!"
As we ate the main course, I thought about how exciting it was to be out here, dressed as a woman, in front of all these people. My body was shaped into a lovely silhouette by the black torsolette, and the blue gown was molded to my every curve. Men's eyes were on me, but they had no clue about the little secret inside my panties. Thank God for the tight control briefs!
More dancing followed the main course, and the girls and I were the targets for every one of the men, except one, a very quiet guy from South Dakota, who hadn't asked any of us to dance. He
looked like he was so shy that if one of the girls talked to him, he'd practically faint. Marsha noticed this, and thought she would have a little fun, so she went around the table, grabbed his hand and asked him to dance. He turned beet-red, but meekly got up and followed her to the dance floor. His face had scarcely gotten any paler when they returned, and Wendy compounded his embarrassment but immediately asking him for the next dance.
Marsha leaned over and whispered to me, "You're next." I protested, but she was insistent, and for the first time in my life, I asked a man to dance with me. I was the aggressor this time, and I could feel his hard-on against me when I held him close to me. He really was shy, I thought, and I wondered how he would feel if he knew my secret.
After the desert and coffee, the party started to break up, and I followed Wendy and Marsha's lead and stood up, saying 'Good-nights' to out tablemates, leaving them, no doubt, very frustrated! We went back up to the suite, and had nightcaps from the mini-bar, the girls kicking off their heels. I didn't want the total feeling to end, though, so I kept mine on. We were sitting on the couch, with me in the middle, and we were soon kissing and stroking each other, knowing that this wonderful week would soon be over, wanting to extend it as long as possible.
When we went into the bedroom, we stood in front of the mirror together, and though I felt a little disheveled, I drank in the image of the three women standing there with a great deal of pleasure. Wendy and Marsha knelt down in front of me, and lifting the hem of my gown, removed the panties I was wearing. They began to lick and suck on my she-male cock, and as the waves of pleasure swept over my body, I continued watching, loving the sight of them as well as the clothes I was wearing.
We fell into bed together a few minutes later, and had a riotous time, making love to each other, delighting in the feel of satin and skin, sharing our last hours in San Francisco. There was a tinge of melancholy in the air, as we showered later, donned our nightgowns and lay in bed together before falling asleep, with only our whispered 'I love you's breaking the silence.
---
That all happened nearly four years ago, and the three of us are still together. We've found that we're extremely compatible, and there is no jealousy among us. The only thing that could be called a disagreement we've had was when I decided, about six months later, that I wanted to have real breasts of my own. Wendy and Marsha were opposed at first, wanting me to keep my male body as it was, but eventually they understood and accepted my desire. That meant, of course, that I would be living full-time as a woman, requiring a complete shift in life-style.
I resigned from my job, and had the surgery and hormone treatments that gave me my breasts, and had electrolysis to remove my beard. The hormones also had the effect of making me considerably less hairy all over, and also caused my figure to assume more womanly proportions. There was one rough time, when my libido went to zero because of them, but the girls were very supportive throughout, once they had accepted my decision. When I tapered off to just a maintenance dosage, everything returned to normal, thank goodness.
I was able to get a job with Marsha's firm for two years, until a managerial position opened up with another company. I applied for it, and was accepted, and when I walked in for the first time, I understood how Wendy must have felt, as an attractive woman, coming in as the new boss. Needless to say, we all attend the annual conference together each year, and look forward to it as
both an anniversary, and as the high point of the year. From time to time, the three of us will select a likely male target, and just have a ball feminizing him, but so far, we haven't found anyone that we wanted to permanently include in our group to round it off as a foursome. The best part of these times, of course, is when our 'victim' discovers the secret inside my panties!