The Next Night - Crossdresser: Part 2 of 2 - Sex Stories

The Next Night - Crossdresser: Part 2 of 2

... 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 ...