The Meet

Like most of my stories, I always like to start with a bit of background, just for those who may not have read any of my other stories. I'm a 20 year old guy from the North East of England, I began to wear my mother's underwear after discovering a lace thong and baby doll set. Since then I've never looked back and have been buying ladies clothing and underwear since I turned 18. Having good job and a car meant I could sneak in a few click and collects to get my fix. The only problem I had was that I hadn't saved enough money for my own place so therefore I was still living at home with my parents. Anyway, enough of that, now on to the story... which was when I was able to live out a major fantasy of mine.

Around a year ago, just before the initial lockdown that started around this time last year, I signed up to a couple of dating sites, one for gay guys and the other a swingers site which were both run by the same mods. I had recently gone through a purge before that and got rid of all my clothes that I had but with the shops closing, I ordered some more stuff knowing I'd be working from home and have the opportunity to wear my panties under my normal clothes everyday.

I filled out my profile with the same information on both and included the same pictures. Some images included me all dressed up and others showed me playing with some of my toys. Also on my profile, I included three different detailed fantasies. They were to be fucked dressed in lingerie, which I already had a tick next to. Playing with more than one guy and the big one that I wanted to achieve was to play with a married couple. This felt like trying to find a unicorn or the end of the rainbow, that was until one day it finally seemed like a possibility.

I received a message one evening from a couple who lived not to far away from the university I was currently studying at. Because I lived about a hour away from Uni, I would often just travel there and back, staying with my parents to save money. The only time I would ever stay over at student accommodation was on a Wednesday night when I had a late lecture followed by an early one on Thursday.

Anyway, I got to chatting with this couple and they told me they could make my fantasy come true. They were a couple in their early 40s and from the pictures they had on their profile, they clearly looked after themselves and the guy looked like he a decent sized cock. I liked to consider myself a bit of a twink and since I began dressing, I would often shave my whole body apart from my hair. They had a lot of verifications on their profile, a lot included bisexual play for them both as well. Eventually due to COVID, we couldn't arrange a social meet to see how we got on, so instead we set up a Zoom meeting, which meant I finally got to put faces and names to the photos I'd seen online.

They introduced themselves as Tom & Lynn. They both looked good for their age, Tom with a bald head but a gym body and Lynn with long blonde hair with a lovely pair of natural tits. We hit it off right away and it was like talking to old friends. The talk quickly turned to my sex life, I told them about the experience I'd had, how it left me wanting more, but unfortunately due to COVID, I felt like a virgin again. I told them about how I started on PrEP after my first experience to be on the safe side.

Lynn then got onto asking me about my dressing. It felt surreal talking to other people about it and she was the first woman I'd ever let see my face after I told them I like to crossdress. I explained my story and how it started out with lingerie and eventually led to more from there.

'Are you wearing panties right now?' she asked me.

I nodded yes in reply, feeling my face blush a crimson red.

'Could we see?' Tom asked.

I nervously stood up, untied my joggers and slowly lowered them to my knees, revealing a candy stripe Victoria's Secret thong with the logo PINK all around the waistband. My cock was soft at first but the thought of showing off in front of other people soon had my cock growing.

I heard Lynn giggle. 'I think he likes showing off', she said. I pulled my joggers back up and sat down. Lynn's hand was now between Tom's legs and I assumed she was stroking his cock. He then stood up himself and I watched as Lynn unbuckled his belt, pulled down his zip and released his cock from his jeans. It was bigger than I thought. My mouth dropped open. It must have been a good 8 or 9 inches and was pretty thick. She gently kissed the head before tucking him back away and he sat back down.

We agreed a date for a meet, they even suggested that I should stay over at their house rather than spending money on student accommodation. Tom disappeared from the chat whilst me and Lynn finalised plans. She asked me what things I already had, and what I needed to bring. She was going to do my makeup and she said she had clothes that would fit me, the rest I needed to bring. She also said that it was unlikely that she would be involved when I meet Tom, although she would be home. Lynn basically told me that she was going to get me ready for him and then she would leave us to it. I wasn't sure what to make of it. But in the build up, I bought myself some new underwear, breastforms and a wig.

My trip to Uni soon came around. The night before, I jumped in the shower and shaved my whole body, packed my overnight bag that I would be taking with me and then jumped into bed, almost to excited to sleep. I set my alarm for slightly earlier than normal, to give myself chance to douche and clean myself once more before slipping into a cheeky pair of panties before throwing on a pair of jeans and t-shirt. All throughout my lecture, I couldn't focus on what was going on, all I kept thinking about what was going to happen when I got to Tom & Lynn's house.

Luckily the lecture seemed to pass relatively quickly and we were out not long after 3pm. After making small talk with some members of my class it was getting closer to 4pm before I was able to make it to my car. Tom & Lynn's was just a short 10 minute drive from my Uni campus so I was there in no time. I immediately became nervous when I got there. They lived at the bottom of a little cul-de-sac in a detached house. There was space on the drive for my car so I quickly pulled up before getting out and knocking on the door.

Lynn answered shortly after, dressed in what I assumed was still her working attire. She looked even better in person, she was wearing her hair in a high ponytail, black trousers which really showed off her ass and then a white blouse with buttons undone at the top, showing off plenty of cleavage.

'Hi sweetie,' she greeted me. 'Come on in, I haven't been home long myself so it's perfect timing.'

I stepped in before Lynn took my overnight bag from me, saying she'd take it upstairs for me. She made a passing comment about how heavy the bag was and was I sure I was only staying for one night. I grabbed a seat in the front room whilst I waited for Lynn to come back. There was no sign of Tom anywhere but Lynn soon returned and joined me.

'Tom won't be long, he's just in the kitchen working.' She said. 'His office don't need him back in yet, plus I think he enjoys the working from home thing. Well at least at first he did. During the first lockdown I was furloughed so I had plenty of time on my hands so he'd get plenty of action. But since I've gone back to work, I've been far to busy for most things, the poor guy is going crazy.'

I laughed but also couldn't get the thoughts out of my head about how hot it would be to suck somebody off under a desk whilst they were in a Zoom meeting. Lynn made us a cup of tea whilst we chatted about things while waiting for Tom to finish up for the day. She pretty much told me about their life story, about how they were swingers and both were bisexual. They'd had plenty of MFF & MMF 3somes and even met people when the other wasn't there. It sounded like the perfect relationship.

She reaffirmed that she probably wouldn't be involved with me & Tom this evening. She said she had lots to catch up on but didn't want to rule it out completely, which was fine with me. After what felt like forever, Tom finally finished his work and joined us and... WOW. That's all I can say. He was at least 6"3 and looked like he was built up of pure muscle. He had just a t-shirt and shorts on and by the looks of it, he was going commando. There was a significant bulge in the front of the shorts that I couldn't take my eyes off. They both noticed and laughed.

After a little more chatting, Lynn stopped the conversation. Reaching her hand out she said, 'Right sweetie, should we get you dressed?' I took her hand and she led me upstairs into the master bedroom which has an en-suite.

'If you want to freshen up while I get everything ready, there's towels in the bathroom and a robe on the back of the door.' I stood in shock, I don't know why but I still felt weird about undressing in front of people. I slowly started taking off my t-shirt and then lowered my jeans before stepping out of them.

'Oooooo... those are cute.' Lynn said, noticing my panties when I stepped out of my jeans. 'Do you always wear panties now then?'

I blushed, 'not all the time, it's mostly when I'm horny or at home, but today is the first time I've worn them to Uni.'

'Aren't you worried about being caught?' She asked.

'Not really, I suppose I am to some extent. Maybe deep down I'm hoping that if girls see me, they might invite me to go shopping with them.' I laughed.

'Oh sweetie, we can go shopping before our next get together.'

Smiling, and feeling good about Tom & Lynn, I jumped in the shower and freshened myself up. I wasn't in the shower long as I'd done most of my prep this morning. I headed back into the bedroom where Lynn was waiting for me, she had set her vanity table up to represent a little slice of heaven. There was all kinds of makeup and then on the bed was the lingerie I'd brought with me and my wig.

'Come on, grab a seat... we haven't got all night,' she said laughing.

I sat in the chair, which she spun to face away from the mirror so I couldn't see what she was doing. And then she began by helping me fix my wig into place which was shoulder length and brunette. She tied it up for me into a messy bun and then began to do my makeup.

Whilst she was working on my makeup, she continued to ask me questions. The first one being how I started into crossdressing.

'I was snooping for Christmas presents in my parents bedroom before I came upon my Mom's lingerie drawer. In there was a red lace thong and a babydoll that I just couldn't resist trying on. After that I was hooked, I started to steal her panties all the time and keep them before I thought she was getting suspicious so I had to stop. Once I had my own job and car, I was able to buy my own. Click and collect has been an absolute lifesaver.'

'So what made you think about having sex with guys?'

'I started watching porn on the internet which eventually led to me finding pegging videos and then sissy videos. Before long I was in deep, researching gay sex, watching videos and reading stories.'

'Ever been pegged?'

'No, I've never been lucky enough, but it's definitely on my bucket list.'

'How many guys have you had sex with?'

'Just the one, he's from around here as well. He picked me up on my lunch break at Uni one day. Took me back to his place, and before I knew it, I was on my hands and knees getting fucked from behind. It wasn't even in the plan but I absolutely loved it.'

'Well tonight, don't be afraid to let go and make as much noise as you need to. I'll just be pottering around the house so you may see me from time to time but don't let that stop whatever your getting up to.'

We must have been chatting for a while because Lynn had finished with my makeup and span me round in the chair. I couldn't believe the transformation. I looked really good, even if I do say so myself. Now I just had to get ready. Lynn said I shouldn't use the breastforms as she thought I'd already look amazing without them, plus I'd enjoy having my nipples played with.

I slipped out of the robe, under the watchful eyes of Lynn before slipping into my lingerie. I'd been told that red was Tom's favourite colour, so I'd bought a red thong, suspender belt and matching bralette for the occasion. With those on, Lynn had me sit on the bed so she could help me into my stockings and then helping me clip to my belt, because they were to fiddly. She then disappeared into the wardrobe before returning with a little black dress.

'This should fit you perfectly', she said handing me the dress. It fit like a glove but was a bit short on me because I was taller than Lynn. It was so short, you could see the tops of my stockings.

'I hope you don't mind but I also bought you these.' I turned and she was stood holding a pair of black heels. For some reason, I almost felt emotional. She had me sit again and helped me into the heels before giving me a quick lesson in walking to make sure I didn't fall. She let my hair out of the ponytail and styled it for me, before putting a bobble onto my wrist.

'It's always easier to put your hair up before certain activities.' She said with a wink.

'Little confession', I said looking at Lynn. 'I've never done anything like this, I normally just wear lingerie and that's it. But I feel amazing so thank you so much for this.'

'Awwww sweetie.' She embraced me in a hug. 'Now let's get you downstairs. Warning though, Tom normally likes to play long and hard with an emphatic ending, but you'll see for yourself'

'TOM', Lynn shouted. No response.

'TOM, ARE YOU READY?' Still no response.

'Come on, let's go and see what he's up to.' She helped guide me down the stairs and back into the front room where he was on the phone talking to someone but that soon changed.

'Sorry mate, I've got to go, can I give you a call back later?' He quickly hung up. 'Shit, is that the same person who you took upstairs?'

I could see a growing bulge in his shorts. He clearly liked what he sees.

'Well I'm going to leave you two to it', Lynn said. 'I'll let you and...'

'Alexis', I interrupted.

'I'll let you and Alexis get to know each other.' She kissed Tom, 'enjoy babe', before she disappeared into the kitchen as I joined Tom on the sofa. Trying not to flash him.

'You look amazing,' he said. I thanked him and we chatted on the sofa, Lynn popping through every now and then. He pretty much asked me all the same questions as Lynn did upstairs. After a while, he leaned across and kissed me. His hand caressing my thigh before he stood before me and took me by the hand and led me upstairs. It did feel a little weird heading to his bed whilst his wife was downstairs.

He closed the door behind him, headed to his nightstand where he got out some condoms and lube before he joined me on the bed. He kissed me once again. His hand cupping the side of my face as his tongue invaded my mouth. I felt so submissive right now and I loved it. I felt like I was melting in his hands. He then started to kiss my neck which drives me wild, his hand dropping to the bottom of my dress before gently grazing the front of my panties which were now struggling to contain my hard cock.

I reached for his t-shirt and quickly removed it from him. Admiring his physique and what looked like 6 perfect abs, I kissed my way down his chest and his abs before reaching his shorts. I dropped to my knees at the side of the bed as I slowly lowered his shorts, freeing the monster cock that was beneath them. My dress had now ridden up and the bottom of my ass was visible as I took his cock in my hands.

That's right... hands, it was that big I needed both hands to get a hold of it. It must have been at least 9" and was so thick. I had no idea how I was going to make it fit. But I was determined to give it a good go. He leant over and gave my ass a strong slap which stung a little, but I liked it.

'Open your mouth.' He said to me, standing from the bed so he now towered over me.

I opened my mouth into the biggest 'O' shape I possibly could and Tom began to push his cock into my mouth and began sliding it as far down my throat as he could before I gagged. I must have gotten at least 3 quarters of it down my throat before it came back out covered in my saliva.

'Do you think you can take it all? He asked me. I nodded, still trying to catch my breath after the first attempt.

This time, he put one hand on the top of my head and guided his cock into my mouth. He went slower this time as I tried to swallow as much of it as I could. I closed my eyes as the need to gag started, but I kept going, eventually feeling my nose pressed against his body, I knew I'd swallowed it all.

He pulled himself back out of my mouth and disappeared into the bathroom and returned with a glass of water for me. I got to my feet, shimmied my dress back down and sipped at the water. Tom jumped back onto the bed, laying down with his massive cock standing upright like a tent pole. I was mesmerised by it and couldn't take my eyes off it.

I placed the glass onto the vanity table and walked to the foot of the bed, his hand gently stroking his cock. I stood, trying to be seductive as possible and slipped the straps of the dress off my shoulders before sliding it down my body, slowly revealing the matching lingerie set I had on underneath, my hard cock still tenting the front of my panties. Tom was just laid on the bed smiling. I kicked the dress off before turning and hanging over the chair next to the vanity table. Taking my time, I slowly bent over, removing each shoe, trying to put on a show for Tom. Finally, I stood at the foot of the bed once more, removed the bobble from my wrist and tied my hair up in a high ponytail.

Tom looked like a kid in a candy store. I never knew this but a lot of guys get excited when a girl puts their hair up in a ponytail. Apparently they think it's some sort of signal for a blowjob. In this case, Tom was right. I slowly climbed onto the bed as he spread his legs for me and I crawled between them. I took his cock in one hand as I lowered my head just below his balls and started to lick the taint in between his balls and asshole.

An approving moan let me know I was in the right place. As I licked away, I slowly used my hand to stroke up and down his shaft, gently teasing the head when I made it to the top. I then moved onto his balls, lapping away at them causing more moans from Tom. Then I tried something I'd never done before but had seen in a lot of porn. I took one of his balls into my mouth, he seemed to like it. Me, I couldn't imagine anything worse. I figured I'd teased him enough, so I licked my way up the shaft of his cock before kissing the head.

I looked up at him with just the tip of his cock in my mouth, he had his eyes locked onto me before closing them and tilting his head back. I went to work on his cock, slowly going up and down the shaft, licking the shaft and doing whatever I thought would make him feel good. And from the moans, groans and shuffling around the bed, it was clearly working.

Then the bedroom door opened, up until this point I'd forgotten I was in another married couples home. I took my mouth off Tom's cock and looked over at Lynn who was coming in with some clothes to hang in the wardrobe. She smiled at me which made me feel at ease, and I went back to sucking his dick.

'You having fun sweetie?' Lynn was at the side of the bed talking to Tom as she leaned down to kiss him.

'Fuckkkk, she's amazing! Only the second best cocksucker I've ever had.' I looked up and Tom was caressing Lynn's pussy through her trousers. She had her eyes closed before snapping back to reality and excusing herself to continue what she was doing. Telling us to have fun before she left.