The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad.

An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers.

I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to meet. Nervously I sat in the bar and looked around; we had only sent each other photos of cocks and pussies, so I didn’t know who I was looking for.

There were several couples that may have fitted the bill that were eyeing me up, especially the men. After a while, I got a text asking if I was in the corner wearing baggy shorts? Because they are in the alcove on the left.

I was wearing baggy shorts and I had chosen to put them on because it gave room for people to feel the goods. I turned and smiled, then went over and sat in the space they made between them in their secluded corner. They were both good looking and very relaxed and I some lost my nervousness. I jolted for a moment as the first hand touched my knee, it was Rosemary’s; I put my hand on her leg only to have it guided under her skirt.

Then there was Julian’s hand creeping up towards my crutch, this time I reached across to his crutch and found his erection. We all knew what we wanted and the contract between us was made. We would go back to their house; I couldn’t stay the night but would get a lift back to my area around midnight.

We walked over to their People Carrier, Rosemary got into the driver’s seat, Julian opened the side door and I clambered in with him. The centre row of seats had been removed leaving a large space in front of the two remaining back seats. The heavily tinted glass made sure nothing could be seen from outside.

Julian sat beside me, immediately his hand stroked my leg; my pulse raced as his digits moved closer to my crutch. He looked into my eyes checking that his advances were still welcome, but all he could see in the half-light was my lust.

He went to kiss me to see if I would turn away, I didn’t; a moment later I was tasting the red wine on his tongue. His fingers ran through my hair, the other hand stroking my cock though my shorts. Gently he pulled the fly zip down and reached inside. He gave a little gasp when he found it was only shorts I was wearing and he had so much room to play. His fingers caressed my soft balls and teased my cock.

“Rosie and I have been talking a lot about you in the last few days. I want to fuck you Anton, will you let me?” Julian purred into my ear.

“Yes please,” I begged.

“I want you to lick Rosie’s cunt while I’d doing that, will you do that for me as well?”

Again I consented, her pussy had felt so wet and sticky in the bar, and my fingers still smelt of it. By now my prick was so stiff I was frightened of wasting my spunk inside my shorts. Julian’s mouth enveloped mine and I let his tongue dance around my own.

Rosemary watched for a while in the rear view mirror for a while and then started to drive. We drove for maybe six or seven miles when stopped down a residential street somewhere. Rosie got out and I started to move too. Julian stopped me.

We watched her open their front door and walk in, a few minutes later a neighbour left and walked across the street.

We followed into the house and shut the door behind us. Julian went straight up the stairs, but Rosie stopped me following.

“Julian and I like a lot of different things, and we want you to dress up Anton, do you mind?” I shook my head.

“He would like to see you in the bra and knickers I’m wearing. Why don’t you reach under my skirt and feel how sexy my knickers are?” A sudden pulse of animal desire came over me; I reach up and felt the lacy material.

“Pull them off me darling,” she ordered.

Rosemary sat on the sofa, her skirt up around her hips, her legs open making no effort to conceal her shaved fanny.

“Now let’s see how they look on you,” she breathed.

I quickly pulled off my shorts letting my stiff cock bounce free; slipping them on I felt the wet stain from her juices had chilled and felt cool against my balls. They were lacy and felt tight against my arse cheeks, I tucked my bell end under the waistband, pre-cum dribbling from its end started to soak into the lacy fabric. It felt so horny; I don’t know why don’t guys wear these all the time.

Rosemary took off her top and exposed her small tits, “Now the bra darling,” she said reaching behind her to uncouple it.

It must have been an A cup, Rosemary didn’t have much more to put in it than I did; her nipples were bigger, but the lace fabric teased mine so much that they were so hard they hurt.

She stood naked beside me, with her square hips, flat chest and short hair, I realised how boyish she looked out of her feminine cloths. She must have read my mind.

“Julian likes to fuck me as a boy, he will love fucking you.”

She led me upstairs to their bedroom; Julian lay on the bed, his silk dressing gown open showing his naked body and hard expectant dick. I was so burning with desire to be used I nearly ran to it.

Rosie lay beside us and guided my head towards her husband’s weapon; I opened my mouth and took as much in as I could. Julian sighed; his fingers traced the cups of my bra then gently pinched my nipple, I felt so good and so sexy dressed like this.

I released Julian’s erection from my mouth for a moment; Rosie quickly took over pushing the prick deep into her mouth, we did this a couple of times before Julian stopped us.

“I want some nice young arse now Anton, will you give me yours?” Julian asked, his hand slid down my back and onto my lace covered bum cheek. I wanted it too and let them move me to the centre of the bed.

Rosie sat at the top of the bed and opened her legs, I shuffled up until my mouth could reach her; behind me I felt Julian pull the back my knickers down just enough to expose what he wanted. I gasped as I felt some cool gel smeared down my crack.

I started to lick the sticky hole in front of me, waiting for the pain and pleasure of being filled with cock. Julian’s naked body covered me, then the hard flesh knocking at my door. A single slow thrust and he was in me. We lay still of a moment both enjoying the experience, then he pushed my head back into the wet slit before me.

Rosie lay back and watched, enjoying the fell of my tongue learning to please a woman and enjoying the sight of her husband buggering my youthful flesh. She watched my face; I was getting close to orgasm just from my body being thrust forward by the invading prick.

She stopped us and rolled us onto our sides, then took my cock in her mouth. Julian’s cock stretching my arse and Rosie’s mouth was all I needed. I gushed into the warm cavern offered to me; she waited for my last few drops then knelt before me.

I watched Julian and Rosie, people I only met two hours ago, share my spunk between them. Julian finally swallowed, and pushing me onto my front again and started with long slow thrusts. As my lover’s pace quickened his wife lay beside me watching me again, running her fingers through my hair. I lay in the spent after-glow of orgasm as Julian pounded my arse, he groaned triumphantly and I felt his pulsing dick filling me with spunk.

For a while we lay as a tangled heap of flesh, then Rosie noticed the time. They told me to keep the bra and knickers until my next visit, so I pulled on my tee shirt and shorts, kissed Julian goodbye and headed for the door.

Rosie told me to sit in the back; we drove a little way before she pulled into a secluded car park. Then she got in the back with me and locked the doors.

“Now it’s my turn,” she said leaning across and kissing me.

Her nimble fingers soon had my shorts around my ankles and just as quickly her mouth found my cock. Rosie lifted her dress as if to take it off, I helped her knowing she was naked under it. In a moment she was straddling me, guiding my stiffy into her wet pussy.

“Nice and tight, is it?” Rosie whispered into my ear. “He doesn’t use that hole all the time, and tonight he will fuck me the way he fucked you.”

As she rode me I thought of Rosie’s boyish body face down on the bed as I was; Julian’s hot breath on the back of her neck and his prick sliding up into her arse was a huge turn on. I felt the yearning in my groin again and focused of my cum.

A week or so later, I had arranged to see a friend, he was generally straight, but that didn’t stop him from sliding his cock into my mouth or arse when he felt like it. I knocked on the door and waited for him; a girl, older than Danny or I answered the door.

“Hi I’m Rebecca, you must be Anton. Come in.” Danny’s sister stepped aside and let me in.

She eyed me up approvingly, “Danny said you were cute, he wasn’t wrong.”

I blushed.

“It’s okay Anton! I know what you and Danny get up to.

I generally prefer girls myself so I guess that evens things up. I’m just having a sort out in my room, so come and talk to me. Danny won’t be long, his train was delayed and the battery of his mobile was flat, so he called the land line to warn me.”

Rachael’s room was a mess, cupboards open and piles of clothes strewn everywhere. We chatted for a while as she inspected another draw.

“You ever dressed like a girl? she asked me as he held up a denim waistcoat. “You have the pretty face and good figure.”

I blushed again thinking of Julian and Rosie.

Rachael saw me colouring up and giggled, “Try that on,” she said throwing it towards me.

It fitted easily and its pinched waist gave me a more feminine look.

“Hey Antonia try the skirt that goes with it,” she threw more denim at me.

I felt a bit embarrassed being called Antonia and being dressed by Danny’s sister, but I turned away to push my trousers down.

“Come on Honey we are all girls together,” she laughed.

I pulled the skirt up; it too was a good fit.

“And get rid of those stupid boxers,” Rachael said throwing me a black thong.

The boxers hit the floor in an instant and soft feminine material was wrapped around my cock and balls again.

Rachael looked at the result and smiled a naughty smile, then she opened another box; I gasped as she pulled a long blonde wig out. Expertly she started to transform me; hair, makeup and flavoured lip-gloss, then pulling my socks off and she knelt to slide a pair of holdups under my skirt and up over my thighs.

She couldn’t have missed my dick, it had broken loose of the thong and now lay stiff along my leg.

“Ever fucked a girl Anton?” she asked softly. I blushed and nodded.

“Did you enjoy it?” Her voice was searching and seductive, I felt a sexy shiver along my spine as I thought of Dianna’s open wet pussy and the hard fuck that Rosie and I had on the drive home, I nodded again.

“Come and fuck me,” Rachael said as she led me to her bed, she pulled her knickers off and lay back, legs open inviting my entry.

“I thought you preferred girls?” I said staring at the dark fanny lips and tuft of brown curls above them.

“Dressed like that Anton, you’re a girl with a stiff dick, what could be better?”

I pulled my skirt up and mounted her; her hand guided my prick to her hole.

“Don’t worry about pulling out when you’re close,” she whispered. “I’m on the pill. Most of my girlfriends are married these days and still have their hubby’s spunk in them when we meet.”

This was only the third pussy I’d been into; she felt hotter than Dianna or Rosie, but still with that feminine wetness. The thought of seeing Danny had made me randy, but my alter ego in girly cloths I was wearing made me even more randy.

It was fast and intense for both of us, my balls slapped against her; her wetness soaking into the thong. I felt a finger crept into my ring.

“Is that where you let your boyfriends fuck you? She panted.”

“Yes they love it and so do I,” I gasped. I knew she must be thinking about me and her brother. I’d seen girls enjoying anal sex on the web and I wanted to try a girls arse, so while her finger was pressed deeply into me I slid my own finger up through her sweaty arse hole.

She gasped and writhed with the intrusion and arched her back forcing her crutch harder towards mine.

We wigged our fingers in each other’s rectums until it was too much for both of us. My balls exploded into her pussy and her muscles greedily milked them dry. We lay exhausted for a while then Rachael hauled me to a sitting position and re-applied my makeup. When Rachael had finished she stood me in front of the long mirror in her room.

Okay, I was flat chested and my hips were square, but my legs were good, my plump round arse the boys liked so much, pushed the denim skirt out behind me. Then the wig, that just made we feel like somebody else, a girl that nobody knew, somebody that could be as bad as she wanted. I felt so sexy and so free.

We heard the front door close and Danny called out as he climbed the stairs.

“We are here in my room,” Rachael answered. “Have you met Antonia?”

Danny stood for a moment staring, checking it was me under my new girly exterior; but he was also checking me out.

“No, but I’d like to,” Danny said, lust burning in his eyes.

He put his hands on my hips and gently backed me back against the wall. His face moved closer to mine, his tongue slid over my glossed lips tasting the cherry lipstick Rachael had applied, then his tongue drove deep into my mouth pushing my head back against the wall. His hands clasped my buttocks, fingers exploring the material of the denim skirt I was wearing; he ground his hips into me and kissed me deeper still. I’d always wanted to kiss him but he never would, for him I was a guy who didn’t mind him using my body for his pleasure, now, dressed as a girl, he wanted me.

He slipped a hand up under my skirt and felt the broad expanse of thigh the thong gave me; then the hands strayed onto my bare buttocks until they found the thin strip of material covering his prize.

“You have dressed to impress haven’t you. Does Antonia fuck on the first date? I hope so because I want to fuck her,” Danny whispered in my ear softly, but the last two words hung in the air.

Normally I was just another guy who asshole he enjoyed, but dressed as a girl it was very different.

He led me to his room, after draining my balls into his sister I felt so submissive that I just knelt on all fours on his bed. It was a way he had fucked me before, now Danny’s hands lifted my skirt exposing the thong I had been given; this was so easy, no fighting to pull trousers down and spoiling the moment as you pulled them and shoes off.

“Let’s get you ready shall we?” Danny cooed from behind me. I felt the little rope covering my tight hole being moved aside; then his tongue circled my anus, it was still sweaty and slick from the fingering I had had in the other room. Then a cool lotion spread between my cheeks and another slippery finger worming into me.

“Good girl,” he cooed. “A nice wet boy pussy waiting to be filled.”

I heard the soft crack of his leather belt being pulled off quickly, then the soft crack between my buttocks filled with a hard cock nudging it. I reached behind me to guide his prick into me, I found it, naked, hard and slick with lube, Danny was going to bare-back me for the first time ever. I held it against my ring and pushed back onto it. he pushed forward and drove his prick deep into me.

“I hope Antonia wants a good hard fuck, because that’s what she is go into get.”

It was what Antonia wanted and I heard myself sighing softly into the pillow. My cock was hard again, but I didn’t care that Danny wasn’t interested in it. My balls were empty anyway, their contains was leaking into another pair of knickers not far away.

Danny was fucking me hard, his prick felt bigger than normal, it should have hurt me more, but I caught sight of myself in his mirror; a girl being taken doggy by a horny guy, I just loved it.

He almost howled when he came, his prick twitched and twitched and twitched and more stuff flowed into me. I felt the big void as he pulled out from me. Even the burning sensation as stretched muscles contracted felt like some kind of pussy I didn’t have before. I stayed on all fours for a while until I had sealed his cum into me.

Then he tugged my legs back and I flopped face down across the bed. Danny lay on top of me.

“Baby, that was good.” He kissed my ear.

Danny rolled to my side and kissed me gently, only then did he reach under my skirt for my cock.

“Do you need this to be sorted?” he asked gently as he caressing my prick. I shook my head and moved closer for another kiss. Then we just lay together.

There was a soft knock on the door, “Hey you two better move before Mom and Dad find Anton dressed in my cloths with that just fucked look on his face.”

I got up and followed Rachael into her room; she took off the makeup and wig. I pulled my boxers over the thong and dressed again as Anton.

“These are too small for me, do you want them,” she asked holding up the cloths I had been wearing.

“Yes please,” I said with a little too much enthusiasm.

I went back into see Danny as Anton, his persona had changed towards me we were guys again, Antonia was a different person and not in the room. We hugged a man’s hug and I left caring a large department store bag Rachael had given me.

That night I looked through it, the waistcoat and skirt were there, the wig, a couple of girlie tee shirts, bra and knickers sets, now too small for her; she had found some pretty pumps for my feet and there was makeup and scent.