I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. 

‘I was just about to wake you up with a blow job,’ she smiled.

‘Funny, I was thinking of doing the same to you!’ I laughed.

Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my lips around the shaft and licking the head with my tongue. I felt Jenny do the same and we settled down to a gentle, slow 69. We sucked and caressed each other for ten minutes until Jenny’s phone started ringing. We broke apart and she jumped off the bed to answer it.

I lay on my side and watched her body as she had a brief conversation. Her voice deepened again and I realised I was watching Pete, not Jenny! Not that it mattered now, as I found myself lusting after him/her no matter what role he/she was playing! I reached down and played with my cock waiting for the end of the phone call. Pete hung up and turned to me, his semi hard cock hanging down his thigh. 

‘I have to go, work emergency. I wasn’t supposed to be on call but the guy covering is ill,’ Pete said.

We got up and dressed, Pete pulling his hair back into his pony tail and putting his glasses on. Once we were dressed I hesitantly went to hug him and we ended up in a full-on embrace and kiss.

‘When can I see you again?’ I asked.

‘Tonight if you want. You have your own place don’t you? I can come over.’ 

I gave him my address and we went our separate ways. I got home and found myself wanting to masturbate but decided to save it for our date. I busied myself tidying the flat as it was in a bit of state since my wife had moved out. I got a SMS message from Pete around 3:00 p.m. saying he’d be there for 7:00 p.m. and could I have some food ready as he’d not eaten all day! We exchanged a few more messages and agreed on pizza. I thought the conversation was over but got a final message saying, 'I’d like you to wear stockings and let me fuck your arse if you’re willing, xxx Jenny.'

I sat down and looked at the message. I figured it was too late to start saying no to suggestions and that I really should try everything once! I sent a message back simply saying okay. I finished cleaning the flat and nipped out to the supermarket for some drinks. As I was doing my usual thing of wandering up and down the aisles browsing, I came across a display of tights and stockings. My heart beating heavily as I selected some black hold-up stockings, a pack of black tights and a pair of black fishnet suspender tights. I could feel myself turning red as I got to the checkout counter with a basket of booze and nylon, convinced the young girl serving me knew what I was going to be doing that evening!

I got home and put the beer in the fridge and checked the time. It was only 5:00 p.m. and I could barely contain myself. I decided I really should go and have a wank or I’d explode as soon as Jenny touched me. I took the packets of nylon into the bedroom and laid them out on the bed. I’d never worn tights or stockings before but as I stripped naked and tried to decide which to try first, my cock was almost bursting. The black tights came in a three pack so I decided to try those first, figuring if I ruined them I had two pairs left! As I pulled them on over my legs, mimicking how I’d seen my wife put tights on, I realised that they didn't give easy access to my bum and that was probably going to be important later. The thought was exciting and nerve racking!

Pulling the nylon over my cock was almost too much but I managed to get them on without cuming and admired myself in the wardrobe mirror. I stroked my cock through the nylon, enjoying the sensation then turned around to admire my bum. I thought my legs looked okay. They were hairless like Jenny’s, but not as shapely. I rubbed my cock through the nylon, bending over to expose my bum in the mirror, imagining Jenny standing behind me with that long, slim cock fully erect and ready to penetrate me.

I thrust my hips back as if I was being fucked and stroked my cock. I found myself thinking back to the night before and the feel of Jenny’s finger in my arse. I continued to stroke and thrust until I was desperate to come. I lay on the bed and pulled the tights down low enough to reach my cock and started to stroke it, reaching between my legs and pulling my scrotum to see what that was like. I found I liked it but not if I pulled as hard as I’d been pulling Jenny. I got into a rhythm and came quickly spraying my belly with cum. I wiped it up with my hand and licked it clean.

I lay there for a minute stroking my legs through the tights then removed them and had a shower. By the time I’d finished it was 6:00 p.m. I grabbed a loser pair of jeans than the ones I’d worn the previous evening and pulled the thigh high stockings on instead of socks. I was going to wear the fishnets but Jenny had said stockings in her text-message so stockings it was! After posing in the mirror for a few minutes I realised I had no appropriate underwear that would go with the stockings. I laughed at the dilemma and simply decided to go commando! I pulled on a t-shirt and shoes then headed downstairs to wait. The stockings under my jeans felt great and I found my cock stiffening again!

Pete arrived just before 7:00 p.m. and after a quick greeting, he went into the bedroom with his overnight bag to change. The pizza arrived just as Jenny made her appearance in the living room. Jenny was dressed in tight denim shorts, black fishnet tights, baggy t-shirt and canvas All-Stars on her feet. A much younger outfit than I’d seen her in before and it occurred to me that although I wasn't sure of her exact age, she was probably ten years my junior.

We ate pizza and drank beer sitting at the kitchen counter chatting amicably. Once we’d finished eating we moved to the sofa, sitting next to each other and watching a film to give our meal time to settle. Jenny kicked her shoes off and I followed suit forgetting I was wearing stockings. 

‘Are you wearing what I think you’re wearing?’ Jenny asked looking at my feet.

‘Hold up stockings, just for you!’ I laughed.

‘How do they feel? Is it good? Are you turned on?’ Jenny asked, excitement evident in her voice.

I told her about my shopping trip and my experimentation with the tights earlier that afternoon, sparing no details. 

‘Show me!’ Jenny demanded.

I pulled my t-shirt over my head and unbuttoned my jeans. I slowly pushed them down my hips, letting Jenny see that I had no underwear on. My cock was hard and sprang out as I pushed my jeans off my hips and down my thighs until finally I stepped out of them and stood in front of her. 

‘I want to fuck you right now before you change your mind!’ Jenny hissed taking my hand and leading me into the bedroom. 

My heart rate soared as we walked into the bedroom and I saw the bottle of lube on the pillow as well as a thick silicon butt plug and a slim, contoured vibrator laid out next to it. Jenny pulled her t-shirt over her head revealing a fishnet bra. She’d not bothered with any padding and I could see her hard nipples pointing through the fishnet. I grabbed her from behind and kissed her neck, watching her reaction in the floor to ceiling mirrors on the built in wardrobe. I ran my hands over her bra and pinched her nipples. Jenny undid her shorts and pushed them down her hips until her hard cock was visible behind the fishnet tights. Jenny was also going commando.

I pulled away from her and helped her out of the shorts. She motioned that I should get on the bed on my back. I laid down, my cock sticking up in the air, and watched her select the butt plug and the lube. I swallowed hard as my mouth went dry thinking it was for me but she smeared it with lube, turned around so I could see, then bent over pushing it down the back of her tights and into her own arsehole. She pushed hard to get it past her tight sphincter and I almost started drooling as I watched her sphincter expand and swallow the plug.

‘Good?’ I asked.

‘Oh God yes!’ Jenny laughed, ‘Your turn!’ 

She got on the bed next to me and made me roll over face down. Again she straddled my legs, this time I had the texture of the fishnets brushing against my own stockings. Another new and amazing sensation. I felt her lean forward and her lips brushed my bum, her tongue flicking out to lick between my cheeks to tease my arsehole. I felt her sit up then the coldness of lube against my bum followed by a single finger. I had my face pressed into the bed up to this point but realised that I could see everything if I just turned my head and looked in the mirrors! 

I turned to see Jenny straddling me with one hand fingering my arse. She reached forward and grabbed the vibrator. It was about 7” long, thinner than either of our cocks but covered in shallow ridges down its length. Jenny kept her finger in my bum and put the vibrator on my bum cheek before squirting a dollop of lube on it. She used her free hand to smear the lube over the vibrator all the time pushing her finger in and out of my arse.

Her finger slipped out and was immediately replaced by the vibrator. It was thicker than her finger but not much thicker than the two fingers she used on me the night before. I could feel the soft ridges as she pushed it deep into my arse. By the time it was fully in me I realised I was being penetrated deeper than ever before! The ridges on the vibe stopped it from slipping easily out of my arse so long as I kept still! Jenny got off my legs and stood at the side of the bed looking down at me. She reached for the remote at the end of the wire sticking out of my bum and pushed a switch.

I jumped as the vibrator started to pulse in my arse, feeling my stiff cock react to the vibrations.

I looked back at Jenny and grinned my approval and she flicked another switch doubling the intensity and frequency of the vibe! I arched my back with pleasure and started to push my hips backwards and forwards rubbing my cock on the bed.

Jenny put the remote down and slapped my bum to make me keep still before straddling me again. She adjusted her cock in her tights until it was pointing directly up my bum crack then lowered herself on to me. I’d never had anyone lay on me before but I liked the feeling. Jenny started to push her hips against my bum pushing the vibrator, which was slowly working its way out of my arse, back inside me. I watched in the mirror as Jenny dry humped me. Her long hair fell over my neck and back tickling and teasing me.

'I’m going to cum if you keep this up for much longer!’ I gasped after five minutes or so.

‘Well we can’t have that just yet!’ Jenny laughed jumping off me.

She left the vibrator sticking out of my arse and stood alongside me. Reaching into her bag she produced a small pair of scissors and started to cut away the fishnet webbing around her cock until it sprang free. She dropped the scissors back into the bag and came back to the bed to stand next to my head. She pushed me on to my side, reaching down to grab the vibrator sticking out of my bum, and rubbed her cock on my lips. I shuffled position until I could open my mouth and suck her cock inside. She fucked my mouth gently for a couple of minutes, fucking my arse with the vibrator but not touching my cock. Without warning she pulled the vibe from my arse and switched it off.

‘Bend over the end of the bed,’ Jenny said in a throaty moan.

I quickly complied, laying on the bed with my feet on the floor and my arse in the air. I turned my head to the side to watch myself in the mirror. I loved the look of my legs in stockings. Jenny spread lube on her beautiful long cock and moved behind me. I felt and watched her place the head of her cock against my anus. I adjusted my stance so that she could enter me smoothly, trying to control my breathing and heart rate as they were both way out of control! She pushed forward and I saw her cock start to disappear into my bum. I pushed back and another couple of inches slipped inside me. My bum stretched to accommodate her and I felt pressure but no pain as my arse opened for her. After a brief pause Jenny pushed her cock all the way into me until our balls were touching.

I arched my back as she began to slowly fuck me. I watched everything in the mirror. Jenny reached around my leg with one hand and curled her fingers around my cock, sliding it up and down in time to her thrusts. The other hand was on my leg inside the top of my stocking stroking my leg. Jenny’s breathing got faster as she kept the same pace on my cock and in my arse. I felt myself starting to build up to orgasm but Jenny beat me to it letting go of my prick and grabbing my hips as she slammed her cock into me harder and faster leaving me gasping for breath. In less than a minute, she pushed her cock deep inside me and held it there, squirting cum inside me. I could feel her cock pulse in my arse and wetness from her cum.

She pulled out of me and immediately bent over the bed next to me. I got up and stood behind her, moving her hips around until she was the right height. I ripped a hole in the fishnet across her bum and pulled the butt plug out of her arse. I looked at it for a minute then reached back and pushed it against my own arse.

‘Oh Christ that’s sexy!’ Jenny said as the butt plug slide easily into my ready arse. 

My arse felt fuller than ever before with the short, but bulbous, plug in. I pushed my hard cock against Jenny’s bum and it slipped in. I didn’t have the patience for finesse and fucked Jenny hard and fast, holding on to her hips to control her movement. I felt myself cuming within a minute, the butt plug against my prostate doing a great job of intensifying my orgasm. This time I pulled out and shot my load over Jenny’s bum and thighs!

I collapsed on the bed next to Jenny and pulled the butt plug out. She joined me and kissed me tenderly looking into my eyes. 

‘Was that as good for you as it was for me?’ she asked gently licking her fingers clean of cum that she’d wiped off her bum.

‘Yes. Both ways. I mean, I loved getting fucked hard by you. I don’t know how I’ve made it into my thirties without experiencing that!’ 

‘Get your breath back and we’ll do it again!’ Jenny laughed.

‘I’d like to finish the 69 we started this morning,’ I admitted. ‘But a shower, a beer and a bit of rest first!’

Jenny nodded her agreement and we took turns showering in my tiny bathroom before grabbing a beer and relaxing on the sofa again. It was a warm evening so we stayed naked, enjoying the breeze from the open windows on our exposed skin. We flicked around watching little bits of programs and films but not settling on anything.

After another beer, Pete started asking me about my sex life. I admitted that it was very vanilla. He was the seventh person I’d had sex with, the others were all women and none of them since I met my ex-wife. The kinkiest thing I could think of, until yesterday, was quietly fucking a girlfriend in the same room as her friend who was asleep on the floor. Pete didn’t judge but surprised me when he admitted I was only the fourth guy he’d fucked and that he’d only been with five women including his current girlfriend. He did admit to sucking off at least twelve guys he hadn’t fucked while dressed as Jenny.

By the end of the confessions session we were both hard again so we switched the TV off and headed back to the bedroom. Pete reached into his bag again pulling out a pair of stockings and a garter belt. He dressed quickly as Jenny as I watched, stroking my cock and any part of her I could reach at any time. 

‘Put the fishnets you bought on,' Jenny said, pulling on her stockings.

I sat on the edge of the bed and pulled them on, noting the difference between fishnet and full nylon. I decided I preferred nylon on the whole but posing in front of the mirror I thought the fishnets suited me more! Jenny led me back to bed and we lay side by side in the 69 we’d started that morning. We started off slowly as we’d done earlier, sucking and stroking each other for ten minutes until Jenny passed me the lube and asked me to finger her bum. I agreed and lubricated my fingers then passed her the lube to do the same. We slowly finger fucked each other, sucking cock at the same time. I pushed two, then three fingers into Jenny’s arse, feeling her do the same to me. 

After another ten minutes of sucking we were both on the brink of orgasm but Jenny stopped and pulled away from me. She rolled me on to my back and squatted over me, grabbed my cock and guided it to her arse then lowered herself on to it. I held my arms up so she could hold my hands to balance and she rode my cock sliding it almost all the way out before sliding down and forcing it back up her arse. She rode me for several minutes then slid off me and knelt between my legs, pushing them apart and entering my arse. 

I was both shocked and delighted with the transition and wrapped my legs around her back letting her cock slide all the way in. She fucked me hard for a couple of minutes then pulled out and lay face down on the bed offering me her arse. I straddled her and pushed my cock up her bum, pushing her long hair away so I could kiss and nibble the back of her neck as I fucked her. Taking my queue from her, I fucked her for a couple of minutes then pulled out, rolled her over and sat on her cock gasping as I sat down too fast and got the full 8” in my arse at once. 

I rode her for a minute but the pressure on my arse was too intense so I pulled off, spread her legs and stuck my cock into her, fucking her in the missionary position. Jenny pulled me to her and had me bite her nipples as we fucked. I came close to cuming again but pulled out and got on all fours offering Jenny my arse. Jenny slipped behind me and her cock was deep in my bum again. This time she fucked me slowly, her hands moving over my legs and thighs. She fucked me for longer this time but eventually pulled her cock out and got off the bed. She walked out into the living room beckoning me to follow.

I chased after her to find her bent over the back of the sofa. I slipped my cock back up her arse, following her lead from last time, slowly fucking her while I stroked her stocking covered thighs. We switched again, this time I sat on the sofa and put my legs against Jenny’s shoulders. She slid her cock in me and sucked my toes through the fishnet. Another new experience and one I was shocked to find really turned me on. 

We switched and I eagerly slid my cock up her bum and took her nylon covered toes in my mouth. If anything sucking her toes was a better feeling than getting mine sucked! I switched feet, trying to suck every toe as I fucked Jenny with more urgency than before. I quickly reached orgasm but pulled my cock out and squirted over her feet. Jenny laughed as I took her toes back into my mouth and sucked the cum off them. When I’d done with her toes she shocked me by leading me out on to the private balcony of my flat and bending me forward over the rail. Her long cock was soon back up my arse as she fucked me hard from behind.

I looked around enjoying the night air on my skin and hoped nobody was in the car park looking up at my flat. I felt Jenny tense as she approached orgasm and I reached behind me to stroke her legs. She pulled her cock out and shot her load over my anus. I felt a second load hit me, then Jenny was on her knees behind me licking her cum up. I felt her rim me and my softening cock twitched again. When she had me clean she got up and we went back into the bedroom and lay next to each other kissing. Eventually we stripped off our stockings and fell asleep utterly exhausted!