Walk On The Wild Side #2

Walk On The Wild Side #2
After my initial foray into the joys of experiencing cock for the first time, I was left in a bit of shock at what had happened. It took me a few weeks to process, and get my head round that I had been fucked by a man, and had the sexual time of my life.
My cousin Paul had sent me a few text messages asking me if everything was alright, not prying into my experience which was nice. Mark also was in regular contact, checking in to see that I was ok. After about Mark's fourth message I felt it was about time to reactivate my new found sex life, so I decided to give Mark a call....
After Mark had taken my gay cherry I had told him about my desire to meet a nice crossdresser. I called Mark and we chatted about my crossdresser thing and Mark said that there was a few low key nights coming up on Glasgow that he knew some lovely gurls would be going to and he thought it might be fun for us to go too.
A wee bit of background, I love the look of crossdressers, lust about them and wank myself furiously to them, especially unconvincing ones....it's what I like!!!
Mark told me about a Gurls Night Out in one of Glasgow's main gay bars Delmonicas in the Merchant City area of the town, we arranged to meet in the Horsehoe bar in the city centre on the Saturday of the party night. Told my wife I was meeting up with a old pal, going to see a band and crashing at his that night.
We meet in the bar, looking like two mates having a beer, not two guys who a short time before had been having amazing gay sex.
After a couple of pints, mainly to settle my nerves we made or way to Delmonicas, because of the Gurls night the door policy was strict, but being with Mark we breezed in.....I could not believe my eyes gurls, gurls, gurls to quote Motley Crue, all shapes, sizes and convincing and especially unconvincing. There was gurls dancing, chatting and generally having a nice safe time to themselves.
We settled in at the bar, but Mark was soon off like a social butterfly catching up with friends, me on the other hand was starting to feel I had made a mistake and I was out my depth. I was getting more uncomfortable with the passing minutes and drank my pint down very quickly and turned to the bar for another, then started watching everybody loosening up more enjoying themselves. Just then Mark returned with a friend he wanted me to meet....
"This is Jackie...Jackie this Waylon" Mark said and whirled away. Jackie was lovely, trim, manly but feminine at the same time, very nicely dressed, LBD and sheer black stockings, black high heels and Cleopatra style hair and make-up, she kind of reminded me of Zoe Fuckpuppet.
"Waylon...that's an unusual name" she said, holding out her hand, gently shaking mine.
"My parents liked Waylon Jennings, the country singer" said I.
She said "I like it" and giggled, the ice was broke. We chatted and had a few more drinks, even a wee dance, then out the blue Jackie asked me to take her back to her flat, I readily agreed, failed to find Mark and we slipped out into a dark Glasgow night.
Jackie was a local girl and lived about a 10min walk from the pub, we made small talk on the walk back, soon enough we where in the lift to her flat.
Once inside, Jackie said "Pour a drink, put some music on and I'll be right back", I did what I was told, poured a couple of glasses of rose wine, impressed with Jackies music collection I put on a Donny Hathaway record. Jackie came back in and woooaaahhh....she had removed her dress and was standing in her stockings, high heels and nothing else, I handed her the glass of wine and took a good look at her fantastic body and delightful cock, smiling she asked if she'd do. "Well you sure will" was all I could get out, I could feel my cock growing and I would see Jackies twitching. Falling into an embrace we were soon kissing very passionately, my clothes were soon discarded, as we fondled and touched each other's bodies, I was gently tugging on her cock and could feel it throbbing, when Jackie pulled away and went to a set of drawers and produced a tell tale small brown bottle of p*ppers, she opened it and offered it under my nose, I inhaled deeply one nostril at a time and felt the euphoric weakness wash over me. Jackie gently pushed me back onto the couch and took my hard cock in to her mouth And started sucking, at the same time she pushed a finger up my now non virgin asshole, as she bobbed up and down she slid her finger in and out, with the great bj, ass massage and p*ppers I literally lasted two minutes before I spurted my load down her throat. Jackie greedily guzzled it down. Now it was my turn, Jackie took a couple of hits of the p*ppers and lay back and offered up her sweet looking chocolate starfish for me to start rimming, I delved right in, loving the tangy taste and sweet smell, licking like a devil I reached up and grabbed her erection and started wanking her off furiously and didn't let up the pace till Jackie moaned, grunted and jerked and shot a beautiful load of cum over her tummy and some got onto her stockings, which I found highly erotic. We retired to her bedroom climbed into bed and literally we both feel asleep right away.
Next morning I gingerly woke up to see Jackie looking just as sexy, even though her hair was messy and her make up smudged. I leaned over and kissed her, and immediately got a rock hard hard on when I felt her 5 o'clock shadow growth, she responded darting her tongue in and around my mouth. I parted and pushed Jackies legs apart and up exposing her asshole, and positioned my dripping cock at her opening, and told Jackie I was about to fuck a bum for the first time, which set her off and she reared her ass off the bed and soon enough my cock was nudging her ass, it really didn't take long and I was sliding my cock in and out her tight ass, as this was my first time fucking ass it didn't take long for me to start emptying my spunk into her and it was wonderful, when I reluctantly withdrew, on impulse I lowered my head and licked up a wee bit of my cum oozing out her hole, on doing this Jackie had a hands free climax, and that how we started a great morning fuck session, after we had a coffee, Jackie decided she wanted to see me in some of her pretty underwear. Jackie went into her room and came back with a very slinky red satin thong and a pair of red hold up stockings which I readily put on and had a wee parade up in down, totally loving the feel and the swishing sound of the nylon as my legs touched as I walked, the exhibitonism, the feel of the underwear and my lust for Jackie had got me rock hard again. Jackie was sitting on the couch purring with desire and sporting a nice erection herself, Jackie commanded "Waylon, stop teasing me and bend over the back of the couch, I'm going to fuck your sissy ass" , I was kind of shocked that my femmine friend had morphed into a demanding alpha at the sight of me in her underwear. It really turned me on, and the damp patch of precum on the panties covered the whole satin material. I positioned myself over the back of the couch and Jackie moved up behind me, pulled the thong to the side and inserted a finger right up my ass, leaned over and whispered in my ear " This time I'm going to be Jack and you are going to be Wendy" ,I nearly came on the spot!!
"Jack" didn't waste any time, no gentleness, he just plunged his hard cock into "Wendy's" ass and hammered it at full tilt for about 5 glorious minutes, grunting like a b**st, then I felt "Jacks" cock twitch and throb, don't know how he managed it but he speeded up to hyper speed and shot a red hot load of his jizz right up my back passage. "Jack" withdrew and walked away, leaving me on my own, spunk dripping down my legs and totally fucked in a real good way.
A few minutes passed and Jackie reappeared in a sheer housecoat, "Sorry about that Waylon, it's just sometimes Jack likes to have some fun too" , I replied "Darling, he is welcome anytime"
Jackie was a picture, blushed and came over and began to attend to my aching cock, she gently slipped it between her lips and tenderly licked and sucked it till I came in her mouth.
After all that excitement we showered and had a chat about all that had happened, we spoke about how much we enjoyed each other, how I Enjoyed meeting "Jack". Eventually it was time to leave, Jackie asked if there was anything she could help me with, I responded "I really would like to have threesome with you and a unconvincing gurl", Jackie smiled and replied "I have a few nice discreet gurlfriends, so I'm sure we'll be able to get together real soon". She gave me a deep sensual kiss and I was on my way back to the real world.
To definitely be continued....