The summer I turned eighteen my life took a new turn. I had planned to go travelling before university, but I was broke. Fortunately my mother managed to arrange a job interview for me at the large department store where she worked. The post was in accounts and stock control and I would be working under the youngest of the four sons who ran the business.
David Gilbey was in his twenties and the interview was pretty informal. A few weeks into the job David asked me to help him with another project, selling surplus stock from the fashion department through online sites. He told me he had set up a photographic area, but needed help shooting the items. He tapped a code into a door at the back of the offices. I followed him up a staircase which led to a private apartment.
“My grandparents lived in this place while they were renovating their house. It’s been used for storage since then, but I took it over a few years ago and refurbished it. What do you reckon?”
“I had no idea this was here.”
“Nobody does. There’s access from the courtyard up a fire escape, but it’s like a secret hideaway.”
There was a huge lounge with a dining area and kitchen at the far end. Two large sofas had been moved to clear a space for photography. There was a camera, linked to a laptop and a mannequin stood against a white wall.
“It’s been a bit tricky trying to do it all by myself. How do you fancy helping with the photography and loading everything into the website?”
I was up for it, much more fun than crunching data in the accounts department. I couldn’t imagine how dull that was going to be for the whole summer. We worked the rest of that day dressing the mannequin in a few different outfits, moving her around so the outfits look as natural as possible and uploading the photos with descriptions.
“Trouble is,” David said, looking at our page on the sales site, “That mannequin doesn’t look right, we could do with a real model.”
“Couldn’t we use one of the women working in the store?”
“No. My brothers approved this idea as long as I didn’t disrupt the store and didn’t spend much money to get it going. They don’t think it will work.”
“We’re stuck with the mannequin then.”
“Unless…”
“Unless what?” I asked naively?”
“Well you’re very slim, you’ve almost got a girl’s figure. I could blur out your face on the pictures so nobody would recognise you.”
It took a second or two for the penny to drop. “You want me to model the clothes?”
“Can’t see another way round it. But you’re right, it’s a stupid idea. I suppose I’d better ditch the whole project.”
I had an image of spending weeks punching numbers into the stock control spreadsheets.
“I don’t think it will work, I don’t really look like a girl, but I could give it a go.”
“Like I said, I can blur out your face, it would mean we could do so many more poses.”
“I suppose so, if you reckon it will work.”
“Why don’t I get us a drink and you could maybe try something on?”
“Yeah, okay,” I said, thinking it would buy me some time while I worked out what I’d agreed to.
David went to make us coffee and I stripped down to my boxer shorts while he was the other end of the room. I managed to wriggle into one of the dresses from the rack. It felt odd and didn’t hang quite right on me.
“It looks okay,” he said, having returned with two glasses. “It’s a warm afternoon, I thought vodka and tonic might be better than coffee. Is that okay with you?”
I didn’t drink that often, but was happy to have something that might quell my nerves. I drank half the tumbler in one go.
David got me to stand in front of the camera and strike several poses. I heard the camera clicking and tried not to think what I looked like.
“I’ve got an idea, just wait a minute, don’t take off that dress yet.” David said and hurried back down the stairs that led to the store.
I sat on the arm of the sofa and sipped my drink, thinking that life would probably never get weirder than this. By the time David returned I’d finished the vodka tonic and was feeling fairly relaxed, all things considered.
“This should help,” he said and held out a collection of stuff from the store. “I’ll refill your glass while you’re sorting yourself out.”
David had brought back a bra, gel inserts, a suspender belt, stockings and panties. I wasn’t sure I wanted to go that far, and I certainly wasn’t changing in front of him.
“Do you have a room I could use?”
“Sure, use my bedroom, it’s that door over there.”
Once alone in David’s bedroom I eased the dress over my head and looked at the items I’d dumped on his bed. I picked up the bra and wondered what it would feel like. It wasn’t like I was gay or anything, this was just work.
I fastened the bra in front of me, pulled it round my body and put my arms through the straps. It felt interesting, like it was hugging me, not entirely unpleasant. The gel inserts were strange to handle. With a little bit of jiggling and pushing I managed to get them fairly even and, I had to admit, they looked quite realistic.
I wasn’t too sure about the stockings, but they would cover up the downy hair on my legs, which might have shown in the photographs. The suspender belt was an even bigger step, but whatever. It was quite tight around my waist, but the actual suspenders hung loose and sort of flapped around. I sat on the edge of the bed and put my foot in one of the stockings.
As I pulled the stocking up my leg I realised why women wore them. The way it smoothed my leg made it look incredibly feminine. Once attached to the suspender belt there was a tension that was actually quite erotic. My cock hardened a little. Putting on the second stocking did nothing to relieve that problem.
The dress had a full skirt, but I didn’t want David to realise what was happening down there so I pulled on the panties that were the last piece from the collection he had supplied. They were satin and held me quite firmly in place. Once again the sensation of being trapped inside those panties was surprisingly pleasant, even the way they stretched across my ass was a novelty that I rather enjoyed.
I let the dress drop over my head and did up the zipper at the side. There was a full length mirror to one side of the bed and I stole a glance in it. My legs looked better than I would have believed and found myself posing to enhance my feminine appearance. From the neck up the illusion ended, I was still me. In a way it looked like my head had been transplanted into a girl’s body.
“How’s it going in there?” David called. “I’ve poured another drink when you’re ready.”
“Okay, I’m coming out, but don’t laugh.”
I half opened the door and felt myself blush as I edged into the room. David looked at me for a few seconds and held a glass out to me.
“You look amazing. It’s going to work fine.”
“You think so?”
“Absolutely, you want to try some poses?”
I drank half the tumbler before I put it down. The vodka had made me a little light headed. I struck various poses under David’s direction, who seemed very happy with the results, but wouldn’t let me see.
That afternoon we shot three more dresses and David had dozens of photos to chose from. While I was changing to go home he worked on just one of them and showed me the result. He’d cropped the photo at my neck and just below my knees. I would never have guessed it wasn’t a real woman and was slightly flustered by how feminine I looked.
“You’re a natural,” David said. “I reckon this is going to work perfectly if you’re up for ir?”
“Yeah, it’s cool I guess. Are we going to do more tomorrow?”
“I’ve got to go to some meeting tomorrow, then I’m away Friday. How does Monday sound to you?”
“Sure, Monday will be fine.” I didn’t want to appear too eager.
“Anyway, you still have to keep up with some of your regular work here. We could shoot in the afternoons if that’s okay with you?”
It was almost time for me to finish work anyway and we parted company with Monday afternoon confirmed. The next couple of days were dull in comparison and on Saturday I moped around the house, not able to think about anything but Monday afternoon.
On Sunday I was soaking in the bath and decided, on impulse, that I didn’t want to have the hair on my legs ruining the look of the stockings. But I didn’t stop with my legs. By the time I was finished I had no hair anywhere below my neck. There was no way my parents would know as my arms weren’t hairy anyway and they were not likely to see the rest of my body. Monday morning I took extra care shaving and set off for work with my mum.
“You seem happier today. Are you enjoying work?”
“Yeah it’s okay,” I mumbled, not wanting to give anything away.
“David’s a nice man. I’ve always thought he was the best of the bunch. How are you getting on with him?”
“Um, yeah, it’s all good.”
“All the women at work suspect that he might be gay. He’s never had a girlfriend as far as any of us know, but he’s so nice, and what would it matter anyway.”
It hadn’t even occurred to me that David might be gay, but why would it, it was me who was posing in a dress, not him. What my mother said was on my mind all morning, but after lunch I was back in David’s apartment, sipping another vodka tonic and flicking through the rack of dresses, skirts and blouses that David had selected for our shoot.
“See anything you like?” David asked.
It was an odd question to answer, it wasn’t as though I was choosing for myself.
“Um, I guess there’s some nice stuff here. I don’t really know much about fashion.”
“Well we’ve got to them all eventually so just pick whatever you want to start with. I’ve left the other stuff on the bed for you.”
I selected a dress and disappeared into the bedroom. On the bed was a small selection of underwear and some holdup stockings, even a pair of shoes with heels. The vodka was already having a nice effect on me and I wondered if David had mixed a stronger version this time.
I took my time, the stockings felt even better now I had smooth legs and they looked great when I looked in the mirror. The dress I had chosen was quite short and only just covered my stocking tops. I wasn’t sure it would look right in the photos if they were showing. I slid my feet into the shoes and they were a perfect fit. Was that just luck or had David chosen them specially. I had a practice walking in them before I came out of the bedroom. I didn’t want to look inelegant, like some clumsy guy in a dress, even though I was a guy in a dress.
There was also a box on the bed. It contained a wig. Given that my face was cropped out of the photos I wasn’t sure what the point of a wig might be.
“David,” I called through the door. “Why is there a wig here?”
“Just thought you might like to try it on.”
He was right, I was sort of fascinated by what I’d look like in it. I eased the wig onto my head. The fringe fell across my eyes and I felt the long brown hair brush my shoulders. The sensation was amazing and I turned to check what I looked like in the mirror. It wasn’t really me looking back out of the glass, it was what my sister might have looked like, if I had one. David was right, I loved the way I looked. I smoothed my dress and flicked my hair back over one shoulder before going back out into the lounge.
“What do you think then?” I asked David.
“Amazing. And the shoes, do they fit okay?”
“Yeah, not bad at all, but a bit tricky to balance in them.”
“You look great and the shoes mean we can keep all of your legs in view. You do have great legs.”
“Thanks,” I said, feeling myself blush.
“I don’t think anyone would recognise you either. With that long hair you are totally a girl.”
I was pleased that David thought I looked so good. The first shoot went fine and I probably posed more outrageously than I had previously. I felt that I had a completely new persona, no longer just a boy in a dress. David suggested I try a skirt and blouse next as he wanted to get some variety into what we were showing.
“I’m not sure the stockings will work though, the skirt is quite short,” he said. “We may have to try with bare legs, but keep the shoes, they make your legs look sensational.”
I popped into the bedroom and slipped out of the dress. I was slightly reluctant to take the stockings off as they felt so nice, especially when my legs brushed against each other, but David was right, they would show beneath the hem of the skirt. It was a summer outfit, a short white lacy skirt with matching blouse and thin cotton jacket. I lover the look, it was kind of ‘innocent and girl next door’. The white skirt gave my legs a nice colour and showed how smooth they were.
David shot that outfit and asked me if I wanted a refill. He went to pour the drinks and I wandered over to one of the Windows on the far side of the room.
“One fresh drink,” he said as he handed me the glass. “Looking at anything in particular?”
“All those people down there.” We were on the fourth floor and the street looked like a highway for ants. “Can’t help wondering what they’d think if they could see us up here.”
“I reckon most of the men would be jealous of me, being up here with you.”
If my mother was right, and I was pretty sure she was right, then David’s compliments probably had a more serious motive behind them.
I had always found it difficult to approach girls and ask them for a date, even to find a compliment that didn’t sound loaded in some way. The probability of rejection always held me back. It was nice to simply be there with David and be the recipient of compliments, especially as David was a good looking guy.
I wasn’t actually expecting David to make a move on me. He was behind me as we looked out of the window. I was sipping my drink, feeling quite relaxed when his hand came to rest on my hip. I froze, but as I didn’t actually say no, my lack of negative reaction obviously encouraged him. He pulled the hair back from my shoulder and kissed the base of my neck.
Several thoughts ran through my head. I loved posing for the camera, which was essentially posing for David. I’d done everything I could to look as feminine as possible. I loved the shiver going through my body as David’s lips pressed to my neck, but I was terrified of what might happen next or whether I could live up to his expectations.
“I don’t know what to do,” I whispered.
“You don’t have to do anything. Do you want me to stop?”
I shook my head. It was madness, but I loved being a girl for David and wanted him to love me too. I let my body lean back against his and the small soft kisses on my neck turned into gentle sucking kisses. David’s hand moved from my hip to the front of my bare thigh, slipping under the hem of my dress. When he covered the front of my panties my hips responded by pushing forward, into his hand. I was hard, but trapped in those satin panties.
David took my hand and led me over to one of the sofas. He sat and gently pulled me onto his lap, I was still holding my tumbler, which he took from me and put on a table. His hand was cool from the glass when it returned to my thigh. I put both my hands on his shoulders and, as his hand on my back pulled me towards him, my arms circled his neck.
There was a moment’s hesitation when our lips were an inch apart. He left me to close that gap and surrender to his command. Our lips brushed softly, almost separated, then our mouths opened for each other and our tongues met. I heard a small sound of submission emanate from my throat as his hand once again slid up my thigh to cover my panties.
There was little that could be described as delicate or subtle over the next few minutes. While we kissed David wrestled my panties until they were hanging around my ankles and his hand closed eagerly around my cock. I knew by the way his fingers explored my balls that he was pleased to find me completely smooth.
Our mouths remained glued to each other, tongues working frantically, as we twisted and fell into a more comfortable position on that sofa. I let David take the lead and held his head in my hands as he kissed my neck. My fingers were still locked in his hair as he moved down my body and I realised I was about to get my first ever blowjob.
When his warm wet mouth moved over the head of my cock I thought I was going to explode, but he kept me in his mouth while his hand moved around my hips and cupped my ass. His mouth moved slowly down my cock, his tongue working all the time.
“Oh god,” I murmured. “I’m sorry, I’m going to…”
I pushed into David’s mouth and my whole body trembled as I came. It was as powerful an orgasm as I’d ever experienced and I groaned through clenched teeth as I pumped repeatedly into David’s willing mouth. He milked every spasm from me with his expert lips and tongue, even returning his hand to squeeze from the base of my cock to the glans and his tongue circled the head to capture that last drop.
As my body shuddered and relaxed he lifted his head and smiled at me. My fingers were still entwined in his hair and I pulled his face to mine. David’s lips were glistening with the residue of my cum and I tasted it for the first time as we kissed. My tongue delved into his mouth, exploring for any last drop. While we kissed he left one hand on the inside of my thigh, softly caressing me. It was David who spoke first.
“It’s getting late, you ought to change to go home.”
“What if I don’t want to go home.”
“I don’t want your mother chasing me, asking where you are.”
“But she likes you.”
“Would she like me if she could see us now?”
I giggled, definitely a girly giggle and David helped me to my feet. He gave me another lingering kiss and patted my bottom as I went off to his bedroom. I felt less confident once I was back in my own clothes and David let me leave without embarrassing me with a kiss while I was dressed in my boy clothes. I was half way the stairs when he leaned over the balustrade.
“I’ll pick out something special for our next photo shoot.”
“I’ll look forward to it,” I replied and tried to act normal once I was back in the offices.
I walked home with my mum and she asked how David’s special project was going. I thought there was an amusement in her tone that suggested she knew more than she was letting on, but maybe I was being paranoid.
The next day I turned up at work only to learn that David had left early to meet with one of their major fashion suppliers and wasn’t expected back for a couple of days. I was annoyed that he hadn’t warned me and turned on my computer, prepared to spend two whole days slogging away at the dullest job in the world. When my screen came to life there was a message, just for me.
‘Looking forward to seeing my super model soon. xxx’
It was an agonising two-day wait, but when David returned he whisked me up to his apartment straight after lunch. At the top of the stairs he was about to kiss me, but I held back.
“Please David, can I get dressed first?”
He smiled at me, brushed the side of my face with his fingers and said he understood completely. I went over to the rack of clothes and looked for something I thought might look sexy. David had added lots more items there, including several pairs of shoes and a selection of underwear. There was a very short flared skirt that looked cute and, because it was black, I chose a pure white cotton blouse to compliment it. There was an idea in the back of my mind that I could look a little like a waitress, and it would be fun to serve David a drink.
“If you pour us some drinks I’ll bring them over to the sofa when I’m changed.”
David agreed and I disappeared into the bedroom, blowing him a kiss before I closed the door. My legs were super smooth so I decided to go without stockings. Among the items I selected were a pair of lacy white ankle socks and some mary-jane shoes with 3″ block heels. I wanted innocent looking underwear and opted for white panties and bra. I’d practiced at home with some of my mum’s makeup and concluded that less is more when your skills in applying it are undeveloped.
Once dressed, and with pale lipstick and the minimum of eye shadow, I slipped back into the lounge. David had put some music on and was relaxing on the sofa with his eyes closed. I picked up the drinks and walked over to him. Either my shoes on the kitchen floor or the ice clinking in the glasses caught his attention.
“Wow,” he said. “You look amazing.”
“Your drink sir?”
I handed David his drink and went to sit beside him, but he reached out and drew me onto his lap. I giggled like a girl and gave him a little kiss on the lips.
“What has my beautiful model been doing while I was away?”
“Pining for you,” I simpered.
David took a sip of his drink and put it on a table next to us. I drank almost half my tumbler before letting David put it beside his.
“My god your beautiful,” he murmured just before he kissed me.
Our tongues played with each other as his hand ran up the outside of my thigh, curling round until his fingertips were caressing my ass. I could feel him growing hard under me and wanted to do anything and everything I could to make him love me more.
David pulled me up and I realised that he wanted me to straddle him, on my knees. I on top of him, kissing him, grinding myself onto his cock, feeling both his hands caressing my ass. I thought I couldn’t have felt more feminine at that moment. It was bliss.
While we kissed David managed to unzip his trousers push them off along with his pants. His hard cock was now rubbing against my panties and his hands returned to my ass. I felt my panties being pulled to one side and his cock instantly nestled between my cheeks. It was so warm and solid and I was pleased that I’d made it that way.
David must have planned some of this as his fingers were sliding over my virgin ass applying some cool and slippery lotion. His finger pressed gently and I think I moaned into his mouth.
“Do you want this my beautiful girl?” He whispered.
I pushed back onto his finger in response and kissed him deeper. David’s finger popped past my ring and sunk into me. It was tight but felt incredibly erotic. I tensed up at first, but he gave me time to adjust and I quickly learned to relax and let his finger move in and out without me clamping down on it. My brain wasn’t in thinking mode by that time, just in pure pleasure mode. All my focus was on his finger turning me into a woman.
“Are you ready for me?” David asked between kisses.
“I’m so ready David,” I whispered into his mouth.
I felt his cock press against my virgin hole. I was scared that it was going to hurt, but wanted it so much that I moved my hips back to increase the pressure. David’s hips rose under me and his cock broke through my ring.
“Oh fuck it’s too big, I’m going to split open,” I said, closing my eyes and biting my lip.
David paused, letting my ass get used to the invasion of his cock. After a minute or so I felt myself slowly relax and as I did his cock slid further in. This time it still felt like I was being stretched beyond belief, but it was also the most wonderful sensation I’d ever known. My whole body was focussed on taking David’s cock and I couldn’t think of anything else. He groaned as he sunk ever deeper into me until I guessed I had taken it all. I kissed David again, my tongue delving ever deeper into his mouth and he began to move inside me.
I had wondered what it might feel like to be fucked, but never realised it would be so amazing. He moved a little faster, his hips lifting my whole body each time he drove into me. Once I knew I could take it all I lost all fear. For the first time I realised that my own cock was also rock hard and I pushed up on my arms so that I could look at David’s face as he fucked me.
My cock was standing up under my skirt. David pushed my hem up and wrapped his hand round my shaft. Every time I rocked on my hips I either drove David’s cock deeper into me or pushed into his welcoming hand. Our rhythms were perfectly matched and I could see in the way David’s eyes were half closing that he was close to a climax.
“Fill me up please David, I want your cum in me.”
He didn’t say anything, but his eyes half closed and I could feel him moving faster until he gave one huge thrust into me. There was a moment’s pause and then his cock pulsed. The sensation drove me over the edge and my own cock jetted out a stream of cum. We moved together, guided by David’s short hard thrusts into my ass.
David’s hand was covered in my cum and I used an index finger to collect some. I moved it to my lips and licked it clean while David watched me and pulsed once more. I giggled, squeezed his cock with my ass and dropped my hand to collect more of my own cum. David held my wrist and pulled my hand to his own lips where he sucked my slippery fingers. I responded by taking his cum covered hand from my cock and licking every last drop, smearing it over my lips.
His hand curled round my neck and he pulled me down to kiss him again. Our lips were slick with my cum. My own cock was shrinking while squashed between our bodies and I could feel David’s slowly withdrawing from me.
We kissed for some time until I realised that it must be almost closing time for the shop and I had to get cleaned up and changed. David asked if I could stay one night, if I could clear it with my parents and make some excuse that would sound sensible to them.
I promised to try, but had no idea how simply things would work out. When walking home with my mum that day, trying to be vague about what David and I had been up to, she leaned close and whispered to me.
“Better clean off that eye makeup before your dad comes home. He likes David, but it might take a little longer for him to adjust to your new life.”
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