Confession and testament of a crossdresser
- 3 years ago
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First Time With A Crossdresser: Part 1 Of 2 free porn video
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 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 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. 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. Jenny shuffled position and presented her bum to me leaning down to kiss and bite my nipples. I gasped as she grabbed my nipple between her teeth and tugged gently.
‘You like that?’ she whispered.
I nodded and moaned as she bit and pulled the other nipple, squeezing my cock as she did so. I ran my hands over her bum and under the thin nylon strip separating her buttocks. My hand brushed her balls and inner thigh briefly before lightly touching her anus. Jenny smiled at me and pushed her bum back against my lightly probing fingers, pushing the tip into her arse. I was surprised to find her bum was moist.
My hand must have twitched away because she whispered, ‘Just lube. Finger me,’ then continued biting my nipples.
I pushed my fingers against her bum and felt my middle finger slip inside. Jenny moaned against my chest and squeezed my cock. I pushed deeper and her head came up. I immediately pulled out thinking I’d hurt her but she pushed back against my fingers in encouragement and bent forward to kiss me hard on the lips, her tongue pushing deep into my mouth. I pushed my tongue against hers and into her mouth as I pushed my finger hard up her bum.
Jenny broke the kiss and swivelled around slightly so I could see her bum. I reached over with my other hand and started to stroke her legs again. I felt hot breath on my cock and without warning Jenny took my entire shaft in her mouth pushing her nose against my balls. I almost shot my load but, with great difficulty, controlled myself. Jenny must have sensed that I was on the edge and let my cock go.
‘You can cum in my mouth another time, I need you to fuck me this time!’ Jenny said, getting off the bed and reaching between her legs to unpop the crotch of her nylon body.
I sat up and pulled my shirt off as I was starting to sweat, as I didn’t have a change of clothing. Jenny’s cock pulled free and I felt my gaze drawn to it again as I tossed my shirt on to the floor. Jenny knelt on the bed again, her long cock swaying between her legs, and kissed me. Again I felt irrational nerves at the thought of her cock swinging free despite having had it rubbed against my cock already. Jenny got on all fours and tossed me a bottle of lube that she’d hidden under a pillow. She presented her arse to me, reaching down and wrapping her hand around her own cock. I knelt behind her and squeezed some lube on to my cock and spread it around. I’d never used it before and put way too much on. I spread the rest on my finders and pushed two of them into Jenny’s arse. She moaned her approval and pushed back against me, fucking my fingers and stroking her cock.
I knelt behind her and replaced my fingers with my cock, sliding easily into her until my balls were pushing against hers. Jenny wrapped her lower legs over mine and pulled forward then pushed back, encouraging me to fuck her. I started to stroke in and out of her slowly at first trying to make myself last but very quickly realised that I was not going to last any time at all. I muttered a warning and pushed my cock deep inside Jenny, squirting cum up her arse. I pulled out and slammed my cock hard back in again, squirting a second time. I kept my cock buried in Jenny’s arse as she moaned and I felt her shiver against me.
I pulled out and moved back on the bed, leaning down to kiss her bum cheeks. I saw that Jenny had also cum, spraying her hand and the bed cover. She turned over and sat on the bed then slowly raised her cum covered fingers to her mouth, licking them clean. I’d never seen anything sexier!
We kissed again and then Jenny stripped naked and we showered together, kissing each other, biting nipples and rubbing cocks although I still couldn’t bring myself to touch it. Without the lingerie and makeup I couldn’t pretend I was naked in the shower with a woman but it didn’t matter. Jenny was hot as Jenny or Pete. When we’d showered, we were both hard again so we dried off and moved back to the bed. Jenny surprised me by pulling the stockings back up her legs and putting the padded bra back on. I realised she was defining herself as Jenny again.
Jenny knelt on the floor and beckoned me over. I stood in front of her and she took my cock in her mouth again. I noticed she had positioned herself so she could watch us in the floor length mirror in the corner of the room. I ran my hands through her wet hair as she sucked me off. Her hands caressed my balls, ran over my bum and teased my arse hole. I’d never been penetrated before and her fingers back there were making me nervous. Again she sensed this and kept her touches light just rubbing my hole and not penetrating.
‘Do you like my fingers there?’ she asked looking up at me, my cock in her hand and wet from her mouth.
‘Yes,’ I said, wondering where she was going with this.
‘Turn around and watch in the mirror,’ she commanded.
I turned around, my heart racing. She made me bend forward slightly and open my legs, exposing my balls and my arse. I felt her hot breath on my bum then the lightest touch on my arsehole. I couldn’t tell or see in the mirror if it was lips or tongue. After the first careful touch Jenny became bolder and this time I could feel her tongue probing my anus. She began rimming me, licking around my sphincter as one of her hands played with my balls and the other with her own cock. I felt her tongue try and then succeed in penetrating me. The feeling was like nothing I’d tried before, and I grunted my encouragement as my breathing sped up. Encouraged, Jenny pushed her face hard against my bum and I felt her tongue penetrate me again. It felt like inches but it was probably only the tip of her tongue!
Jenny rimmed me hard for a couple of minutes then turned me around again to take my cock in her mouth. This time when she pushed her fingers again my arse, I let made no sound or movement, letting her slip her middle finger inside me. Again it felt like I was impaled by something huge but I could see in the mirror that was only fucking me up to the first knuckle of her middle finger. I wanted more but I was too nervous to ask. I showed my encouragement by fucking her mouth, pushing my arse back on to her finger, feeling a little more slip inside me.
Jenny stopped me and told me that if I wanted to go any further with the anal play then she needed some lube. I nodded my agreement and I fetched it from the bed. Jenny took my cock in her mouth as she opened the bottle and deftly squeezed lube on to her fingers, spreading it between my cheeks and on to my arse hole. I felt her middle finger slide inside me, more comfortable now with the lube and the previous penetration. I pushed back to let her know I was comfortable and was shocked to see her entire finger slide up my bum! I tried to pull back in shock but she kept her finger deep inside me. I relaxed as I realised that not only did it not hurt, the feeling was fantastic!
Jenny took my entire cock in her mouth and I felt a second finger pushing against my arse. Before I could get nervous it was inside me and Jenny was finger fucking me as hard as she could in the position she was in. I felt myself building up to cum again and started bucking my hips against Jenny’s mouth and fingers. My orgasm started much deeper than normal and I felt like I wanted to pee! My legs buckled slightly and suddenly my entire body was shaking as I squirted cum down Jenny’s throat. Jenny pulled her fingers out of me triggering a second orgasm and I started to collapse pulling my cock out of her mouth and spraying a second load over her neck. I sat on the floor and Jenny grabbed my cock again, sucking and milking me until I was dry.
She leant forward and kissed me, the taste of my cum on her mouth. I kissed her back, sucking her tongue. She offered me her neck and I greedily lapped up my juice. I’d tasted my own cum before but not for years and realised how much I enjoyed it. Jenny stroked my back and pulled my mouth to hers to kiss me again. Then broke away and moved to the bed.
‘I need to cum now,’ she said, ‘would you like to help me?’
I nodded and stood up to find my legs were a bit wobbly! I joined her on the bed, kneeling next to her and stroking her thighs as she started to slowly stroke her cock. Her legs parted, one leg resting on my thighs so I could stroke her thigh. I moved my hands further up the leg to her inner thigh and gently stroked her balls with the back of my hand. My heart beat faster as I grew bolder and cupped them, pushing my hand underneath to touch her anus.
Jenny whispered her approval and stroked my thighs and cock with her leg. My cock reacted and started to get semi hard. Her hand left her cock and stroked her belly. With only a moment’s hesitation I reached forward and wrapped my fingers around her cock and started wanking her off. My free hand stroked her thighs and balls.
‘Pull my ball sack,’ Jenny whispered.
I grabbed the skin of her scrotum between two fingers and gently tugged in time to my strokes on her shaft. Jenny put her head back in pleasure and pushed her fingers under her bra to pinch her nipples. I grew hard against Jenny’s leg, growing bolder with my mounting excitement and pulling her scrotum harder as I increased pace on her cock. Jenny moaned and bucked her hips, fucking my hand. I shifted position, spreading her legs and sitting between them so I could bend down and kiss her thighs. Jenny moved one hand to my head and stroked my hair as I explored her thighs with my mouth and my hands worked on her cock and balls.
Jenny whispered that she was getting close and to keep going just as I was. I was pulling her scrotum hard now, tugging and stretching it away from her. Her hand grabbed my hair and pulled my face down on to the top of her thigh, the shaft of her cock just centimeters away from my mouth. I put my tongue out and licked the base of her shaft then removed my hand and, in one smooth movement, took her cock in my mouth. I could feel her precum on my tongue. Jenny released her grip on my hair now that she had my mouth where she wanted it but stroked my neck and shoulder as I explored her cock with my mouth.
Just as I was settling into a rhythm and enjoying the sensation of sucking cock, Jenny called a warning that she was ready. I kept my mouth on her cock but didn’t take her too deeply as I was now determined she was going to cum in my mouth! Jenny grunted and her body stiffened as my mouth was filled with her salty spunk. I swallowed the first load and sucked greedily at her cock for more, milking her dry. I released her cock and balls and leaned forward to kiss her. Her tongue explored my mouth and her legs wrapped tightly around my thighs holding me to her.
‘Not bad for your first time!’ Jenny whispered.
‘I was just getting into it when you came!’ I laughed.
Jenny kissed me again, her legs pulling me into the missionary position. I could feel the head of my hard cock pushing against her balls and bum as we rocked together and kissed. I moved my hips, thrusting gently against Jenny’s body. Jenny reached for the bottle of lube that she’d left on the bedside table and handed me it. I squeezed out a smaller dollop this time and kneeled back to spread it on Jenny’s anus. She spread her legs, holding her thighs to give me full access. Another dollop of lube went on my dick and I moved forward pushing my cock against Jenny’s arsehole.
My cock slipped up Jenny’s arse in one, smooth movement and she moaned into my mouth as we kissed. Her legs wrapped around my thighs and she rotated her hips, pulling me fully on top of her, allowing for deeper penetration. I started to slowly fuck and kiss her and heard the plastic cap of the lube bottle snap open. I felt Jenny’s hands on my bum then the cold lube dribble on my arsehole followed by her finger probing me. I pushed my tongue deeper into her mouth in an attempt to let her know I was willing. Her hands parted my cheeks and I felt a finger from each hand slip into my anus, slowly pushing deeper and stretching me open.
Jenny started slipping her fingers in and out of me in turn so there was always one deep inside me as the other slid out! I gasped as my body reacted to the stimulation, feeling my cock and balls twitch. I started to fuck Jenny faster, pushing myself up with my arms so I could slam my cock into her arse as hard as possible. Jenny was breathing hard and her fingers lost their rhythm, but they had done enough and I shot my load deep inside her.
We untangled our bodies and lay panting next to each other. Jenny turned over and lay on my chest, kissing me gently. Eventually we got up and showered again, drying off and getting in bed. We talked about sex for an hour – what we’d done and who with, but I quickly ran out of interesting stories so I listened to her tales before falling asleep.
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 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 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. 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. Jenny shuffled position and presented her bum to me leaning down to kiss and bite my nipples. I gasped as she grabbed my nipple between her teeth and tugged gently.
‘You like that?’ she whispered.
I nodded and moaned as she bit and pulled the other nipple, squeezing my cock as she did so. I ran my hands over her bum and under the thin nylon strip separating her buttocks. My hand brushed her balls and inner thigh briefly before lightly touching her anus. Jenny smiled at me and pushed her bum back against my lightly probing fingers, pushing the tip into her arse. I was surprised to find her bum was moist.
My hand must have twitched away because she whispered, ‘Just lube. Finger me,’ then continued biting my nipples.
I pushed my fingers against her bum and felt my middle finger slip inside. Jenny moaned against my chest and squeezed my cock. I pushed deeper and her head came up. I immediately pulled out thinking I’d hurt her but she pushed back against my fingers in encouragement and bent forward to kiss me hard on the lips, her tongue pushing deep into my mouth. I pushed my tongue against hers and into her mouth as I pushed my finger hard up her bum.
Jenny broke the kiss and swivelled around slightly so I could see her bum. I reached over with my other hand and started to stroke her legs again. I felt hot breath on my cock and without warning Jenny took my entire shaft in her mouth pushing her nose against my balls. I almost shot my load but, with great difficulty, controlled myself. Jenny must have sensed that I was on the edge and let my cock go.
‘You can cum in my mouth another time, I need you to fuck me this time!’ Jenny said, getting off the bed and reaching between her legs to unpop the crotch of her nylon body.
I sat up and pulled my shirt off as I was starting to sweat, as I didn’t have a change of clothing. Jenny’s cock pulled free and I felt my gaze drawn to it again as I tossed my shirt on to the floor. Jenny knelt on the bed again, her long cock swaying between her legs, and kissed me. Again I felt irrational nerves at the thought of her cock swinging free despite having had it rubbed against my cock already. Jenny got on all fours and tossed me a bottle of lube that she’d hidden under a pillow. She presented her arse to me, reaching down and wrapping her hand around her own cock. I knelt behind her and squeezed some lube on to my cock and spread it around. I’d never used it before and put way too much on. I spread the rest on my finders and pushed two of them into Jenny’s arse. She moaned her approval and pushed back against me, fucking my fingers and stroking her cock.
I knelt behind her and replaced my fingers with my cock, sliding easily into her until my balls were pushing against hers. Jenny wrapped her lower legs over mine and pulled forward then pushed back, encouraging me to fuck her. I started to stroke in and out of her slowly at first trying to make myself last but very quickly realised that I was not going to last any time at all. I muttered a warning and pushed my cock deep inside Jenny, squirting cum up her arse. I pulled out and slammed my cock hard back in again, squirting a second time. I kept my cock buried in Jenny’s arse as she moaned and I felt her shiver against me.
I pulled out and moved back on the bed, leaning down to kiss her bum cheeks. I saw that Jenny had also cum, spraying her hand and the bed cover. She turned over and sat on the bed then slowly raised her cum covered fingers to her mouth, licking them clean. I’d never seen anything sexier!
We kissed again and then Jenny stripped naked and we showered together, kissing each other, biting nipples and rubbing cocks although I still couldn’t bring myself to touch it. Without the lingerie and makeup I couldn’t pretend I was naked in the shower with a woman but it didn’t matter. Jenny was hot as Jenny or Pete. When we’d showered, we were both hard again so we dried off and moved back to the bed. Jenny surprised me by pulling the stockings back up her legs and putting the padded bra back on. I realised she was defining herself as Jenny again.
Jenny knelt on the floor and beckoned me over. I stood in front of her and she took my cock in her mouth again. I noticed she had positioned herself so she could watch us in the floor length mirror in the corner of the room. I ran my hands through her wet hair as she sucked me off. Her hands caressed my balls, ran over my bum and teased my arse hole. I’d never been penetrated before and her fingers back there were making me nervous. Again she sensed this and kept her touches light just rubbing my hole and not penetrating.
‘Do you like my fingers there?’ she asked looking up at me, my cock in her hand and wet from her mouth.
‘Yes,’ I said, wondering where she was going with this.
‘Turn around and watch in the mirror,’ she commanded.
I turned around, my heart racing. She made me bend forward slightly and open my legs, exposing my balls and my arse. I felt her hot breath on my bum then the lightest touch on my arsehole. I couldn’t tell or see in the mirror if it was lips or tongue. After the first careful touch Jenny became bolder and this time I could feel her tongue probing my anus. She began rimming me, licking around my sphincter as one of her hands played with my balls and the other with her own cock. I felt her tongue try and then succeed in penetrating me. The feeling was like nothing I’d tried before, and I grunted my encouragement as my breathing sped up. Encouraged, Jenny pushed her face hard against my bum and I felt her tongue penetrate me again. It felt like inches but it was probably only the tip of her tongue!
Jenny rimmed me hard for a couple of minutes then turned me around again to take my cock in her mouth. This time when she pushed her fingers again my arse, I let made no sound or movement, letting her slip her middle finger inside me. Again it felt like I was impaled by something huge but I could see in the mirror that was only fucking me up to the first knuckle of her middle finger. I wanted more but I was too nervous to ask. I showed my encouragement by fucking her mouth, pushing my arse back on to her finger, feeling a little more slip inside me.
Jenny stopped me and told me that if I wanted to go any further with the anal play then she needed some lube. I nodded my agreement and I fetched it from the bed. Jenny took my cock in her mouth as she opened the bottle and deftly squeezed lube on to her fingers, spreading it between my cheeks and on to my arse hole. I felt her middle finger slide inside me, more comfortable now with the lube and the previous penetration. I pushed back to let her know I was comfortable and was shocked to see her entire finger slide up my bum! I tried to pull back in shock but she kept her finger deep inside me. I relaxed as I realised that not only did it not hurt, the feeling was fantastic!
Jenny took my entire cock in her mouth and I felt a second finger pushing against my arse. Before I could get nervous it was inside me and Jenny was finger fucking me as hard as she could in the position she was in. I felt myself building up to cum again and started bucking my hips against Jenny’s mouth and fingers. My orgasm started much deeper than normal and I felt like I wanted to pee! My legs buckled slightly and suddenly my entire body was shaking as I squirted cum down Jenny’s throat. Jenny pulled her fingers out of me triggering a second orgasm and I started to collapse pulling my cock out of her mouth and spraying a second load over her neck. I sat on the floor and Jenny grabbed my cock again, sucking and milking me until I was dry.
She leant forward and kissed me, the taste of my cum on her mouth. I kissed her back, sucking her tongue. She offered me her neck and I greedily lapped up my juice. I’d tasted my own cum before but not for years and realised how much I enjoyed it. Jenny stroked my back and pulled my mouth to hers to kiss me again. Then broke away and moved to the bed.
‘I need to cum now,’ she said, ‘would you like to help me?’
I nodded and stood up to find my legs were a bit wobbly! I joined her on the bed, kneeling next to her and stroking her thighs as she started to slowly stroke her cock. Her legs parted, one leg resting on my thighs so I could stroke her thigh. I moved my hands further up the leg to her inner thigh and gently stroked her balls with the back of my hand. My heart beat faster as I grew bolder and cupped them, pushing my hand underneath to touch her anus.
Jenny whispered her approval and stroked my thighs and cock with her leg. My cock reacted and started to get semi hard. Her hand left her cock and stroked her belly. With only a moment’s hesitation I reached forward and wrapped my fingers around her cock and started wanking her off. My free hand stroked her thighs and balls.
‘Pull my ball sack,’ Jenny whispered.
I grabbed the skin of her scrotum between two fingers and gently tugged in time to my strokes on her shaft. Jenny put her head back in pleasure and pushed her fingers under her bra to pinch her nipples. I grew hard against Jenny’s leg, growing bolder with my mounting excitement and pulling her scrotum harder as I increased pace on her cock. Jenny moaned and bucked her hips, fucking my hand. I shifted position, spreading her legs and sitting between them so I could bend down and kiss her thighs. Jenny moved one hand to my head and stroked my hair as I explored her thighs with my mouth and my hands worked on her cock and balls.
Jenny whispered that she was getting close and to keep going just as I was. I was pulling her scrotum hard now, tugging and stretching it away from her. Her hand grabbed my hair and pulled my face down on to the top of her thigh, the shaft of her cock just centimeters away from my mouth. I put my tongue out and licked the base of her shaft then removed my hand and, in one smooth movement, took her cock in my mouth. I could feel her precum on my tongue. Jenny released her grip on my hair now that she had my mouth where she wanted it but stroked my neck and shoulder as I explored her cock with my mouth.
Just as I was settling into a rhythm and enjoying the sensation of sucking cock, Jenny called a warning that she was ready. I kept my mouth on her cock but didn’t take her too deeply as I was now determined she was going to cum in my mouth! Jenny grunted and her body stiffened as my mouth was filled with her salty spunk. I swallowed the first load and sucked greedily at her cock for more, milking her dry. I released her cock and balls and leaned forward to kiss her. Her tongue explored my mouth and her legs wrapped tightly around my thighs holding me to her.
‘Not bad for your first time!’ Jenny whispered.
‘I was just getting into it when you came!’ I laughed.
Jenny kissed me again, her legs pulling me into the missionary position. I could feel the head of my hard cock pushing against her balls and bum as we rocked together and kissed. I moved my hips, thrusting gently against Jenny’s body. Jenny reached for the bottle of lube that she’d left on the bedside table and handed me it. I squeezed out a smaller dollop this time and kneeled back to spread it on Jenny’s anus. She spread her legs, holding her thighs to give me full access. Another dollop of lube went on my dick and I moved forward pushing my cock against Jenny’s arsehole.
My cock slipped up Jenny’s arse in one, smooth movement and she moaned into my mouth as we kissed. Her legs wrapped around my thighs and she rotated her hips, pulling me fully on top of her, allowing for deeper penetration. I started to slowly fuck and kiss her and heard the plastic cap of the lube bottle snap open. I felt Jenny’s hands on my bum then the cold lube dribble on my arsehole followed by her finger probing me. I pushed my tongue deeper into her mouth in an attempt to let her know I was willing. Her hands parted my cheeks and I felt a finger from each hand slip into my anus, slowly pushing deeper and stretching me open.
Jenny started slipping her fingers in and out of me in turn so there was always one deep inside me as the other slid out! I gasped as my body reacted to the stimulation, feeling my cock and balls twitch. I started to fuck Jenny faster, pushing myself up with my arms so I could slam my cock into her arse as hard as possible. Jenny was breathing hard and her fingers lost their rhythm, but they had done enough and I shot my load deep inside her.
We untangled our bodies and lay panting next to each other. Jenny turned over and lay on my chest, kissing me gently. Eventually we got up and showered again, drying off and getting in bed. We talked about sex for an hour – what we’d done and who with, but I quickly ran out of interesting stories so I listened to her tales before falling asleep.
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- 11.12.2022
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