That was this summer. I had very long relationship and last year i got ridden of it. So I sex occasionally wit various girls till then. One night this September I was very very tired of everything. Job went finally better and some private investing also, but I had being working for 14 hours a day at time. It was About 1 am in the morning and was just went of from long shower and about to lay down on my bad.The voice from the other side of cell phone was very pleasant, some kind of baby talking voice. Voice said" Annnn' what what do want from me now?...LOL.. i said "who is this?&... Continue»
I was still horny for Heather after our suckfest the previous night, when Lynda asked if I was free this week. She’s married, and doesn’t get the chance to meet very often and when she does it’s usually short notice. We had chatted a few times, and had agreed to meet up sometime, although she doesn’t meet for sex, just dressing and chatting. Lynda had booked a room at a hotel on the off chance that someone was available, and I agreed to meet her there.
We agreed to meet in male form, and then get dressed up, as it made her more at ease, and she didn’t want to go out dressed up. It didn’t bother me, and I packed a bag with some clothes, shoes and 2 wigs, I had decided to try brunette as well as blonde. I was meeting her at 8pm, and she called to make sure I was still coming. ‘I’m in room 24’ she told me, and I left for the hotel.
Entering the room, I saw Lynda, although it looked nothing like her at all. I was thinking to myself, ‘I should get out of here’, but then she spoke. ‘Hi Lisa, not quite what you expected is it?’ I nodded in response. ‘It’s ok it happens all the time, but you’ll see me once I’m dolled up’. We chatted for a bit, and I could see she was really nervous, the same way I was when I met Jane. After about half an hour, we thought we’d better get ourselves dressed up. We helped each other put make up on, and then she left to the bathroom, to get dressed. I stripped off, and put on some black stockings, suspenders, black mini skirt and top with my dark wig.
After a few minutes, Lynda appeared, what a transformation, she was gorgeous. Smaller than me, about 5’8ish, but had a slim hourglass figure and wore clothes that really showed it off. Anyway she was wearing a minidress, which hugged every curve and 3inch heels. ‘Lynda, I can’t believe the transformation. You look absolutely gorgeous.’ I managed to utter in total shock. ‘Thanks honey, that’s the usual comment someone gives me’, she replied laughing. That broke the ice and we settled down to take some pictures, some of me, some of her and some together. I was conscious that she didn’t want anything more, so didn’t push it, however it wasn’t long before her hand was on my leg.
We sat down, and chatted, she had her hand on my leg, so I put my arm behind her, and started to stroke the back of her neck. She started to moan a little, and move her hand up to my thigh and I knew I had her. I leaned over a bit and started to whisper in her ear, and I could see her squirm with delight and pleasure. We kissed, just a small one, but a kiss just the same, and by now I had my hands on her legs, and had moved hers up to my ass. I love having my ass teased and squeezed, and I wanted Lynda to do it. She re-positioned her body so I could get easier access to her, and slowly I moved my hand up her leg. I was getting horny now, and wanted to move things along, but ‘what the fuck??’ she was wearing tights, talk about a turn off. I suggested that we change clothes and take some more pictures.
I changed into a cream outfit this time, cream skirt, top and white stockings, with white heels, I looked like an Essex girl, but if it was going to get Lynda’s knickers down I’ll give it a go. Lynda came through this time in another mini dress and knee high boots. My cock almost exploded at the sight. Again we spent time taking pictures and chatting, but this time the pictures were getting raunchier. We were hugging and I was flashing stocking tops and wrapping my leg around her body, and kissing her full on. As we moved closer I could feel her cock starting to harden, so I made another move on her. Back on the couch, I laid my leg on top of hers, and let her play with it for a moment before I moved in again. Lynda was getting horny, I could tell as she let my hand wander up and play with her cock, albeit covered by tights again. ‘What do I have to do to get at her cock?’ I asked myself as I was beginning to get frustrated. I know she wasn’t looking for sex, but after some of the playing we did I was getting horny and wanted to suck her off. We spent the next few minutes kissing and fondling each other, although she kept away from my cock, but that didn’t bother me, as I was after hers.
There was one more clothe change, and I pulled out the big guns so to speak. I got the black fishnet stockings, with red lingerie, and a very short red dress. Redid my makeup, with bright red lippy, and blonde wig and red heels. If this wasn’t advertising what I was after nothing was. This time Lynda was wearing a skin tight dress and fishnets too, oh how I hope those are stockings I thought to myself. Well I need not have worried, as she very quickly hitched her dress up to reveal stockings. ‘Fantastic’ I thought, ‘I’ll be sucking tgirl cock tonight’.
The pictures didn’t go on for long this time, as I got Lynda onto the bed and we rolled around kissing and fondling and I got my hand under her panties onto her cock. She jerked as I touched it, but instead of pushing my hand away, she just opened her legs more. I pulled her panties to one side and released her hardening cock, it felt good as it got hard in my hand. She was now completely lost in my lust, and even pulled her dress up so it was easier for me to masturbate her. I was wanking her hard, and sticking my tongue down her throat at the same time, and she reciprocated, but fondling my balls and touching my cock. ‘Oh Lisa, that feels so good. I can’t believe you can make me this horny’ she whispered. ‘Oh honey, you’ve not seen anything yet’ I replied, and with that I took her cock in my mouth. ‘Oh fuck Lisa that is so good. It’s been ages since someone sucked my cock’. I lifted her legs up and spread them wide so I could get right into her cock and balls. I was teasing and sucking, and massaging her whole genital area, and she was moaning with delight and lust, and she was rubbing on her breasts. ‘Oh my god honey, you are so good at that….oh fuck that’s….oh god….mmmmmm I want you honey’. ‘You’ve got me babes’ I replied ‘I’m going to suck you dry tonight’, and went back down on her nice firm cock. ‘No Lisa, I want you. I want you to fuck me please’. ‘Wow, seriously Lynda, are you sure?’ ‘Oh fuck yes Lisa, take my virginity and slide your cock up my tight ass’
Never one to refuse any invitation to sex, I went through my bag and found some lubricant. I always carry some for my butt plugs and dildos, but this was the first time I was lubing for anal sex. Lynda rolled onto her front, and then up on her knees, pushing her ass in the air. I started to tease her hole with the tip of my cock, trying to make it relax and open up for me. Lynda was moaning with delight as I touched and prodded her asshole with my cock, and with one hand I was stroking and pulling on her cock, keeping it hard but making sure she didn’t cum just yet. It was taking time for her to loosed up enough for me to penetrate, but I was determined that she was going to get fucked after begging me to do it. Slowly her hole started to open, very slightly at first, and just enough for the head of my cock to touch her insides. I could feel her shiver with anticipation as I gently slid my cock into her tight hole, an inch at a time. It wasn’t too long till half my cock was in her, and wow what a feeling, as I slowly started to fuck her. Both my hands very now gripping her ass, holding her in position as I thrust in and out of Lynda’s hole. She lifted her head up off the bed, and I could see the expression of pain and pleasure on her face, as she turned to look at me fucking her. ‘Oh yes fuck my pussy babes, fuck me hard’, she begged ‘oh fuck yes Lisa, fuck me please, I want to feel you cock in me’. I stood, and leaned back on my heels, and pulled Lynda further onto my cock, until I was in all the way up to my balls, and I really started to thrust my body into hers. ‘OH FUCK’, was all she could manage, as she was in a total state of lust, as I kept pounding away at her pussy.
Lynda’s cock was now hanging down semi flaccid as she had her first orgasm of the night, she didn’t spurt cum, but she definitely came. I pulled out, and went back down and started to suck her off as I wanted her cock to be hard for me for when I’m ready for her to shoot spunk into my mouth. She was moaning and groaning begging me to fuck her and make her cum again. I laid on the bed, and got Lynda to position herself on top facing me and lowered herself onto my cock. It went in easier this time, and she started to bounce up and down while she wanked herself with each thrust of my cock. I was pounding hard, when I could see that Lynda was close to cumming, so I increased the speed of my thrusts as I wanted to shoot at the same time, and fill her ass with my cum. Her moans were getting louder and louder as I thrust deeper into her pussy. ‘OH FUCK Lisa, I’m going to cum, oh fuck…..oh fuck. Harder please, fuck me harder…yes yes yes, oh fuck I’m cumming…….fucking hell I’m fucking cumming’. With that Lynda shot her load, all over me, hitting my face, tits, and clothes, I was absolutely covered in her cum, but I didn’t care I just kept on fucking. ‘OH FUCK Lynda, I’m going to cum’ and she pushed down on my cock as hard as she could as I exploded inside her. ‘OH Babe, I can feel your spunk dripping in my pussy. That feels wonderful’. She smiled as she climbed off me, my cum dripping out of her ass and onto my cock.
We lay on the bed, both totally knackered and smelling of cum. I used my fingers to clean my cock, and tasted my juices, which were mixed with lubricant and Lynda’s ass. ‘mmmmmmm that tastes good, cum and ass together’ I told Lynda as I let the cum drip from my fingers into my mouth. ‘I bet it does’ she replied, but unfortunately she didn’t want to taste it. She lay beside me for about 15minutes, before she got up and took a shower and changed back into male clothes. She thanked me for a pleasant night, and said she had to get up early tomorrow, so I tidied myself up, said goodbye and left. I never heard from or saw Lynda again after that, and she left the site not long after that night. Not the way I wanted to finish my first anal experience, but I still had Heather and that’s what mattered.