First Time With A Crossdresser: Part 1 of 2First Time With A Crossdresser: Part 1 of 2


I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than four hours of sleep a night and often found myself up late alone. One night when I was bored and horny I found myself looking for more than the vanilla porn I usually watched and found a website full of erotic stories. I started to read and discovered a world of fetishes some of which I didn’t even know existed and some I’m still not sure I understand! I read more over the following months and started hanging out on the chat boards as my marriage came to an end and I wasn’t getting any sex! I soon found out that chat on porn sites is dominated by men and the few women that appear are usually hounded until they leave. Of course you sometimes find yourself talking to a woman who turns out to be a man! The first couple of times this happened I spotted them pretty quickly and disconnected but eventually decided to carry on the conversation to see where it went as I was getting nowhere finding real women! I began to chat to ‘Jenny’ carrying on the pretence that she was a woman despite my suspicions. Once in a private chat Jenny very quickly admitted to being a cross dressing bisexual man and apologised if that offended me. I was quite surprised to find that it didn’t and that I was enjoying the flirty conversation we were having. As we chatted more and Jenny described the stockings and heels she was wearing and how she would love to bend over for me and expose herself, I found myself getting a very impressive erection. I played with myself as Jenny described how she liked to be fucked. A picture came through on the chat showing Jenny bent over the bed wearing a garter belt, stockings and high heeled ankle boots. Her bum and legs were hairless and her upper torso was hidden. Her legs were together so I couldn’t see her cock. I pictured myself fucking her arse, something I’d never done before, and came hard. At Jenny’s insistence I took a picture of my semi hard cock and cum covered hand and groin and sent it back to her! We settled into a pattern, meeting online twice a week. Jenny sent me one picture per session, always a different pose and always wearing sexy lingerie. Her instructions were to send her a picture back of my cock with her picture visible. Once she had the picture we described how we’d like to fuck, Jenny going into detail on how she’d feel my cock slipping up her man pussy. I did my best to match her description but found it difficult to express myself. Jenny said she didn’t care as she got off making me get off. When I came I had to take another picture of my cock and cum and send it over. At first Jenny’s pictures didn’t show her face or chest but slowly she revealed more of herself to me until one day I got a full frontal picture güvenilir bahis with her face visible. She was wearing a long sleeved body stocking and high heeled shoes. Her cock was hard behind the sheer nylon and her body was hairless. I’d joked that she wouldn’t send me a face picture because of her beard but I was pleasantly surprised to see a pleasant androgynous face with long blonde hair and minimum makeup. I took my regular picture of my cock near her picture but before I hit send I ran into the bedroom and took a full frontal, nude selfie in the full length wardrobe mirror. My heart skipped a beat as I walked back into the study and saw Jenny’s picture on the screen. I uploaded and sent the two pictures, eagerly waiting for a response. I’ll give you a quick description of myself. I’m 5’ 11’, slim with decent muscle tone from cycling, short light brown hair, sparse chest and pubic hair. My cock isn’t an impressive internet cock – it’s 6’ fully erect, uncut and average girth. In the picture I’d just taken it was fully hard which pulls my foreskin back and exposes the cock head! Jenny responded straight away with two pictures. One of her still wearing the body stocking and standing next to her laptop with my picture visible. The second picture of her face next to my naked picture blowing my cock a kiss. Now we both knew what we were getting! I sat down and started massaging my cock waiting for Jenny to message me. Instead of the description of sex I was expecting I got: Want to meet IRL? From the conversations we’d had, I knew Jenny was a closet bisexual cross dresser. I knew she had her own flat and a girlfriend who was unaware of Jenny. When she met up with men it had always been at their place or a hotel. I also realised I didn’t know what her real name was or even where she lived! I panicked a little and didn’t respond and got another message from Jenny saying: Don’t be freaked out! I quickly responded that I wasn’t freaked out. Then sent another message admitting I was freaked out but incredibly turned on by the thought. Jenny suggested that maybe we should go for a drink first and get to know each other in real life. Once we’d done that we could go back to messaging and see how I felt about Jenny then. I suggested maybe a video chat but Jenny admitted that she’d had a very bad experience with video chat before. I finally thought ‘fuck it’ and agreed to meet up. Jenny told me she would be meeting me as Pete! We agreed on a chain hotel about half way between us, only a ten mile drive as it happened. Pete would get a room and we’d meet in the bar for a drink. If we hit it off he would go upstairs to dress as Jenny then send me an SMS to come up. If we didn’t hit it off in the bar we’d walk away with a handshake. I spent the next three days fretting about what was going to happen. This was the first date I’d been on since I met my ex-wife fifteen years ago and it was hardly your typical date! The day came and I dressed casually in jeans, suede desert boots and a plain shirt. I drove to the hotel and parked in the car park taking fifteen minutes to calm down and another five to get up the courage to walk across the güvenilir bahis siteleri car park and into the bar. I’d expected this to happen and had arrived thirty minutes early so I wouldn’t be late! The bar had a couple of early evening drinkers in but they were all older looking men. I ordered a pint of bitter and found a table where I could sit and watch the entire bar. Pete walked in a couple of minutes after me. He was as slim as the pictures of Jenny promised and a little shorter than me. He was dressed in a pair of chinos, casual shirt and canvas baseball boots. My heart skipped a beat when I saw that his long blonde hair was tied back in a ponytail. I was expecting Jenny to wear a wig for some reason. His face was framed with a pair of masculine frameless glasses. I caught his eye and he waved, miming did I want another drink. I realised I’d already finished my drink and nodded yes. I stood up and took my pint and shook Pete’s hand noticing that his hands were slim and soft. I’ve shook a lot of men’s hands and never had that thought before! We hit it off immediately, finding common ground in cycling and chatted casually about nothing in particular. We spent an hour chatting and had another couple of drinks to help us relax. Pete finished his third drink and asked if I was still willing. I almost forgot what he meant and stuttered yes! Pete got up and said he’d need fifteen minutes and would send me an SMS with the room number when Jenny was ready. Just hearing him use his female name got my cock semi erect and pushing against my tight jeans. I sipped the remains of my drink and watched the minutes tick by on my phone but still jumped when I got a message alert from Pete with his room number. My heart was beating hard in my chest as I finished my drink and headed for the lift. The lift door opened and I stepped out on to a long corridor. The SMS had said to turn left, walk to the end of the corridor then turn right. I followed the instructions, turned the corner and came face to face with Jenny standing in the door way of her room. She was dressed in a tight black top, short denim skirt, black stockings and the lace up high heeled ankle boots I’d seen in her first picture. I knew Jenny wore padded bras to enhance her chest but was still surprised to see the tight top bulging over small breasts. Jenny had let her hair down, put make up on and the glasses were missing. Jenny smiled at me and beckoned me inside. My cock was pushing against my jeans again as I followed her into the room. Jenny asked me if I needed another drink and I shook my head. Her voice was a more feminine version of Pete’s. I wanted to kiss her but didn’t have a clue if that was the right protocol for this situation! Jenny led me into the room and, sensing my unease, asked me what I thought of the view.I said, ‘It’s not as nice as the view in here,’ trying to sound gallant and failing. We looked at each other and cracked up breaking the tension. Jenny walked up to me and gently kissed me on the lips, putting her hand on my waist. In heels she was about the same height as me. My cock responded to the kiss, pushing against my jeans again. iddaa siteleri I kissed her back putting my hand on her back and waist. We kissed gently at first then with more urgency. My mind was reeling with thoughts and sensations. I could feel her cock pushing against mine through the two layers of denim. My mind told me I couldn’t feel any beard stubble. Her hand was under my shirt stroking my back; this should be wrong but feels so fucking right! Jenny broke away from me and told me to sit on the bed. I laughed that I couldn’t do that just yet as my jeans were too tight! Laughing she told me to take them off, then sit down. I unzipped and pulled my jeans down revealing my boxer trunks stretched over my cock. I kicked off my shoes and got rid of my jeans and socks then sat down on the bed. Jenny smiled and started to sway her hips and unzip her skirt. She slowly pushed it down her legs revealing her hard cock contained by a sheer nylon body and hold up stockings on her long slim legs. The pictures I’d received always played down her cock but despite the restraint of her underwear I could see it was about the same girth as mine but much longer and circumcised. I figured it was close to 8” long! I swallowed hard as I realised we’d always talked about what I would do to her but nothing about what she would like to do to me! As if sensing my thoughts Jenny smiled and leaned towards me whispering, ‘This is all about you, baby,’ as she kissed my ear.She pushed me on the bed so I was on my back and asked me to shuffle backwards so she could straddle my lower legs. I unbuttoned my shirt as she leant forward and lightly kissed my cock through my underpants. I felt precum leaking out as my balls twitched at the touch. She leaned forward, her nylon legs brushing against mine and licked my belly then both nipples before finding my mouth and pushing her tongue past my lips. I kissed her back as she lightly brushed her cock against mine. I ran my hands over her lower back to her bum. The body she was wearing was a thong back so I found myself caressing skin. Her bum was slim and obviously boyish but as my type has always been slim, athletic girls I barely noticed! She pushed herself against me, grinding our cocks together through our underwear. I’d had no desire to touch her cock up to then but I began to wonder what it would be like to touch a cock not attached to me! We kissed for a few minutes, then Jenny sat up whispering that she needed to see my cock right now. She jumped off the bed and pulled her top over her head fully revealing the black nylon body and a black padded bra underneath. I ran my eyes over her body almost salivating with lust until my eyes went to her cock. Again I imagined touching it and wondering what it would be like. Before I could consider my new cock obsession any further, Jenny reached forward and pulled my underpants off, causing my cock to spring up. Throwing my underpants on the floor, Jenny joined me on the bed kneeling to my side then reaching forward to take my cock in her hand. I watched with my mouth open as she slowly ran her hand up and down my shaft then pushed my legs apart to caress and gently squeeze my balls. I stroked her thigh with my left hand as she slowly wanked me off. The feel of cool nylon on a warm leg sent shivers down my spine! My hand wandered up her thigh, feeling flesh at the top of her stocking, exploring her thigh and hip.

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