My name is Jamie. Growing up in the UK, I’d always lived in the Northeast of England. As I got older, I always thought I was going to be your typical young lad. I used to check out girls asses as they walked past me and when I jerked myself off daily, it used to be whilst I was imagining fucking a girl from my college class. That girl used to change daily. But when I turned 20, things started to change for me. Ever since I’d seen my first whale tail in college, I’d had a severe interest in lingerie. Whenever I was watching porn, if the woman wasn’t wearing lingerie or more specifically panties, I tended to turn it off.
My experiences with women and their lingerie though was very limited. I’d only ever been with one girl and that was a drunken escapade one night after too many drinks. I don’t remember much other than her lingerie wasn’t sexy, and she was that bored of me, she fell asleep before I had time to orgasm. My curiosity was peaked even further when I was in college. A girl sat in front of me in science class had the biggest ass I’d ever seen, and, on this day, her jeans started to hang really low revealing a plain white cotton thong that had me adjusting myself under the desk. She wasn’t the type of girl I’d ever expected to wear thongs but of course being good friends with her, I couldn’t resist giving her a wedgie which was a major risk, but she took it really well.
But then she got her revenge, she yanked my boxers so far up my ass that they pretty much turned into a thong. And do you know what, I really liked the way it felt. So much so that I immediately went home, waited for my sister to disappear, and started rummaging through her underwear drawer looking for a thong that was so far at the back that she might not notice if it went missing. I found a plain looking black one and took it back to my room, tried it on, loved the feeling and ended up jerking myself off while I was wearing it. I thought I might have looked ridiculous, but it wasn’t that bad. But if my friends knew, my life wouldn’t be worth living. I was very sporty, so I had a decent body, and I was around 6ft3 so I wasn’t a guy you could imagine walking round in a skimpy pair of panties.
Over the next couple of years my love life took a complete 360 spin. My obsession with lingerie became larger to the point where I only wore panties. I’d bought my own now, so I didn’t have to steal from my sister anymore. I had every style of pantie and every material that they could be made from. I only kept a couple of pairs of boxers for any medical appointments or when I was playing sports. I’d even started wearing panties to work, hoping that nobody would notice. And now I was nearly 23 my sexual interests had completely changed as well. I’d started watching more transsexual porn, crossdressing porn and pegging. I’d taken a serious interest in being the person on the end of the cock rather than the person doing the fucking, which I later learned was called ‘bottoming’. I’d even gone as far as arranging to meet another guy, but he tried to fuck me, and I struggled to take it, he then sucked me off, I came within seconds, and I left embarrassed.
Since then, I’ve been more adventurous with my ass play at home. I’ve bought dildos and plugs which have helped get me a lot more used to taking things and even learned to get pleasure whilst doing it. That meant that my lingering thoughts about taking a real dick never went away and that’s where Nikki comes into it. I’d signed myself up to an online gay dating site and it wasn’t Grindr for those wondering. It was one I think was only known in the UK and it was on this site where I met Nikki.
Nikki was a 20-year-old crossdresser who had to move back in with her parents when COVID struck because she could no longer afford her own place. This made her dressing difficult, and I completely understood where she was coming from seen as though I’d been hiding my love for lingerie for the last 3 years. A couple of times my parents had gotten suspicious of me but every time they did, I was able to pass off the misplaced panties as something a hook up had left behind the night before. Me and Nikki had started exchanging pictures and she really put me to shame in the cock department. Her cock must have been at least 6 or 7 inches long and super thick whereas mine was a purely average 5 inches and averagely thick as well.
Whilst we were chatting, Nikki told me all about her experiences she’d had getting fucked and that just made me want it even more. Nikki also did live cam shows on a night during COVID and had carried these on whenever her parents were out of the house. And that’s when I got to see that cock live in action as she gently stroked it whilst making hundreds of guys incredibly horny including myself. We used to message while she was on cam, and I’d always tell her how I’d imagine being on my knees in front of her sucking on her giant cock whilst I was wearing a pair of panties and hold ups. And then I asked her the magic question, defne escort ‘would you be willing to fuck me for the first time?’ And I got the answer I wanted, a resounding yes. But after that, Nikki didn’t reply to my messages, so I left it for a week or so and messaged again, and again no response even though they’d been online. Another one I’d scared away.
And then a few days later a message came through that read, ‘Thank you for enquiring about the services of Nikki. Please contact my master through his page “tgirltrainer”, thank you.’ I replied to that message to ask if she was okay, but I didn’t receive a reply, so a couple of days later I looked for the profile that she’d mentioned in her message. The profile was for a 66-year-old man and all his photos were of various different crossdressers either sucking his dick or being fucked by one another. I had a look through some of the photos and recognised that Nikki was in some of them purely from looking at their cocks. In the end I bit the bullet and message the account stating that I would be interested in meeting Nikki and what I needed to do.
A message came back quickly, and I was directed to another website where he’d set us his escort business and if I wanted to meet Nikki then I’d have to arrange a meet through there. I was starting to get concerned that there could be a major fee involved but I was willing to pay so much if it meant I could taste Nikki’s cock. So anyway, I set up an account on this escort site and followed the link he sent me which took me to his profile. On his profile he had even more pictures of the girls he worked with, including some of Nikki’s face which I’d never seen before. Seeing her all dressed up made her look incredible and she looked even better when someone had their lips wrapped around her cock. So again, I sent him a message and below is how the exchange went:
Me: Hi, I’d love to arrange a meet with Nikki, if possible, please?
tgirltrainer: Hi, Nikki isn’t available for the next couple of weeks. I have other girls available who could meet your needs?
Me: I’m only looking to meet Nikki thanks; we’ve been chatting for a while, and I’d really like to meet her. Do you know if she tops?
tgirltrainer: Nikki can top, she’s very versatile when it comes to sex. Is that what you’d be looking for?
Me: Yes please.
tgirltrainer: That’s fine. I can book you in for 2 weeks on Wednesday if that works for you. We do 1 hour, 2 hours or 3 hours depending on how long you need.
Me: Can I book in for the 3 hours please?
tgirltrainer: Ok. For 3 hours its £210?
Me: Erm, that might be a little more than I can afford at the moment, I’ll get back to you, thanks.
Over £200 felt like it was a bit excessive, and I wasn’t even sure if this bloke was who he said he was. He had reviews on the escort site, but I was still a little wary of committing to anything just yet. But a few days later another message came through:
tgirltrainer: Hi, I’ve been speaking to Nikki, and she explained your situation, so I’m willing to do the 3 hours for £130? You’d need to pay £50 today via bank transfer and then the rest in cash on the day.
Me: That sounds great, I really appreciate it. If you send your details across, I’ll sent the money across now.
He sent me his bank details and I sent him his money. The meet was scheduled for two weeks from today. He sent me his address and obviously reminded me that I needed to be clean and presentable for the meet, but I could wear anything I wanted. He also warned me that there could be other girls their working or even some other clients. I looked up his address on maps and found that he lived in quite a large house that must’ve had at least five or more bedrooms. The last thing he told me that it would be up to me to decide whether we played safe or not. Nikki would be tested as she regularly would be, and I would also need to provide documentation to say I was if I wanted to play without condoms.
The two weeks that went by seemed to go so slowly. I was eagerly awaiting the day to come so that I could finally meet Nikki. It was made worse that there was no contact between me and Nikki or even her master. It had me on the edge wondering whether I’d done the right thing, but I tried to not let my mind take over too much and tried to focus on looking forward with what was coming. I’d also made the decision that I didn’t want to use condoms and I wanted Nikki to fuck me bareback. So, a week or so before the arranged meet, I booked myself into a sex clinic and got myself tested. Of course, they asked me all the usual questions about how many sexual partners, and whether I was planning on having unprotected sex soon. When I answered yes, I blushed immediately before she asked whether this would be with a man. Again, I blushed but admitted it was. She then explained to me what PrEP was and prescribed me some tablets which I should take 3 days before and 3 days demetevler escort after the sexual activity.
Also, in the build-up, I went shopping for lingerie. Whilst I was out and about, I went into Victoria’s Secret and took advantage of their 5 for £30 offer they had on, and I even splashed out on a pair of the rhinestone side brazilian for the occasion. I even bought myself a new pair of thigh high stockings and a pair of crotchless pantyhose as I still wasn’t sure which I wanted to wear. Finally, after what felt like an eternity of waiting, the day of the meet had finally arrived. On the morning of the meet, I got up slightly earlier than I would normally do for work and snook my douche into the shower and made sure I was thoroughly cleaned before getting dressed like it was a normal day at work. Only this time, I had my new panties and a pair of thigh high stockings on. The night before the meet I’d decided that it would look better if I shaved my legs and ass. It felt amazing and was something I wished I’d tried sooner.
I’d told my parents that I was still working but had booked the day off with my manager. So, I left the house at my usual time and headed straight for the coffee shop in town. Careful not to eat anything, I got myself a bottle of water and read my book for an hour or so. I didn’t realise until I’d been sat there for a good 20 minutes that because I was sat with one leg crossed over the other, my jeans had ridden up my leg and you could see the stocking in between my socks and jean leg. I quickly readjusted and tried to calm myself ahead of making my way over to the house. With about 20 minutes to go before the arranged time, I jumped into my car and headed over to the house.
When I arrive at the house, it was much bigger than your bog-standard town house. And his driveway was private and where you parked your car couldn’t be seen from the main road meaning there was no chance of being spotted by someone who knew you. Getting out of the car, the palms of my hands were sweaty as I approached the front door and knocked. The guy from the escort profile answered which was a relief, so at least I knew I hadn’t been given some random address. He asked me who it was I was here to see and when I confirmed that, he smiled and asked me for the rest of the money. He also took my documentation for my sexual health check-up, gave them a once over before handing them back to me.
‘You’re in for a real treat,’ he told me as he took my money and led me to the main living room. The living room was ginormous, there was four sofas set out into a square with a table in the middle of them. On three of those sofas were three gentlemen who were older than me, I would say one guy in his 30s and the others in their 50s or 60s and each one was sat with beautiful woman in a various state of undress. Some you could see obvious bulges. There was plenty of touching going on but nothing more than that.
‘Nothing sexual ever happens in here,’ he told me as we continued into the living room. ‘You can spend time in here getting to know your girl, get undressed to your underwear and your three hours will start once you make it up to her room.’
I was in awe looking round at all these other guys who were clearly here for the same thing as me. In the corner of the living room were some smaller seating areas and there was a crossdresser who looked around my age sat on an old man’s lap before they got up and she led him by the hand towards the hallway and up the stairs. Both smiled as they passed me. The owner of the house directed me to the empty sofa and told me to take a seat whilst he went and got Nikki for me. So, I poured myself a fresh glass of water from the table and waited, watching the other people around me as another two couples disappeared off upstairs.
My first thought was to make sure that none of these recognised me but then again with the girls, they all looked that good that there was no way I could’ve told who they were in their normal day to day lives. I also couldn’t help but think whether any of these other guys were here to be fucked or whether they were here because they wanted to fuck a beautiful girl who had something extra between their legs. I waited for Nikki to arrive with eager anticipation.
And then five minutes later, I felt a hand on my shoulder as someone made their way around the front of the sofa and into my line of sight. In front of me was what I could only describe as a beautiful woman. Yes, I know she was a he, but they looked incredible and could easily pass if they were out on the streets. Nikki was dressed in a lovely red dress which had a flowing skirt that stopped around her knees, a pair of black fishnet tights finished with a pair of black flat shoes.
‘Hi sweetie,’ she greeted me with a kiss on the cheek before sitting down next to me.
‘Ermmm… wow,’ was all I could muster up in response to which she laughed.
She placed her hand on demirözü escort my thigh, ‘are you looking forward today?’ She asked me.
‘Very much so,’ I said with a smile on my face. ‘But I’m nervous at the same time. I’ve seen what you’ve got to work with and the last guy I was with was a bit of a dick.’
‘Aww sweetie, you don’t need to worry today. I’m glad you’ve booked the three hours because it gives me longer to get you nice and relaxed.’ She was very reassuring, and then she leaned across and kissed me on the lips for the first time.
For a moment I was taken out of the room as she pushed her tongue into my mouth. It felt like we were the only two people in the room. As she kissed me, she grabbed a hold of my hand and placed it on her ass. It felt great and I was already starting to grow impatient, I wanted to be alone with her now.
‘I think we already know enough about each other that we can head upstairs, don’t you?’ She enquired.
‘Absolutely,’ I replied trying to stand but she put her hand back on my thigh to indicate that I shouldn’t go anywhere.
‘I seem to remember that you have a lingerie fetish… is that right?’ She asked to which I nodded in reply.
She then leaned in and whispered into my ear, ‘are you wearing some right now?’ My face must’ve turned bright red but again, I nodded.
‘Well then, before we go anywhere, I want you to take off your clothes. Is that okay?’ She put her hand under my chin and turned me to face her before kissing me again.
Now I was shitting myself. I’d never been dressed in front of anybody before, let alone a room full of people. But Nikki stood first and pulled me to my feet. I initially stepped out of my shoes and pulled my socks off revealing that I did have stockings on underneath. She then helped me out of my t-shirt before pulling at the buttons on my jeans. Suddenly it felt like all eyes in the room were on me. Nikki then shimmied my jeans down my legs and helped me step out of them. I was now standing in a room full of strangers in just a pair of VS panties and stockings. A few wolf whistles and claps emanated around the room. I feel like Nikki could sense my embarrassment and she quickly picked up my clothes and ushered me to follow her upstairs. Once upstairs, she closed the door behind us and locked it. Our time started now.
She threw my clothes into the corner of the room and embraced me in another kiss. All felt much better now, and now that we were alone, I could feel myself starting to stiffen inside my panties. Nikki noticed and gave me a slight brush across the front of the panties. She continued to kiss me as she pushed me towards the bed before I fell onto it with Nikki landing on top of me. She roamed my chest and played with my nipples whilst her tongue was down my throat. Eventually, Nikki slid herself off the bed and onto her knees, her hands on my thighs gently massaging up and down, getting closer to my cock with each rub.
Her hands were then in the side of my panties, releasing my cock and balls before she gently started to play with my balls whilst slowly stroking my cock. The hand that was playing with my balls was then moved away before being replaced by her tongue. She started licking just below my balls but above my ass and it felt incredible. I couldn’t help but moan as my toes curled from the pleasure. Her mouth was working wonders and then she licked her way up from my balls and slowly worked her way from the base of my shaft to the head of my cock. Then I felt the warm sensation of her mouth swallowing my cock whole and she was able to take it easily.
Nikki had her tongue circling my cock which was bringing me towards the brink of an orgasm. I thought not jerking off would keep me horny, but it seemed like it was going to bring an abrupt end to my morning with Nikki. ‘Oh, fuck if you keep doing that, I’m gonna fucking cum’, I moaned.
I felt her mouth leave my cock as well as her hands. ‘In that case, I better stop then, hadn’t I? She said giggling. ‘Before you undress me, I want to see that ass. Turn around and get on all fours for me.’
Reluctantly, I got up and spun myself round on the bed, presenting my ass to her. I’d never felt this vulnerable with somebody else before. Then I felt a firm slap on my ass, and then a second followed quickly by a third. Then she grabbed a hold of the waistband of my panties before pulling them further into my crack. My other ass cheek then received the same treatment of three spanks.
‘You have such a nice ass,’ she told me as she rubbed her hands over my cheeks. ‘Nice and smooth as well and there’s nothing, I enjoy more than burying my face in a nice smooth ass.’
The panties I was wearing were then pulled to the side and I felt the warm breath around my ass as Nikki moved her head towards my asshole. ‘Spread those cheeks for me sweetie.’ I moved my hands to my ass which left my head buried in her bed sheets. I spread my ass cheeks, exposing my asshole to her which was twitching in anticipation of what she was about to do and then I felt it. Her tongue made contact with my ass.
‘Uh fuck, that feels good,’ I moaned in glee as she continued to work my ass. My dick remained rock hard beneath me and I knew that any sort of friction could tip me over the edge.
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