CHAPTER 9 JENNY THE STRAP-ON
I had just finished with a girl that had, quite frankly, done my head in and was not really looking for a girl when I met Jenny. She was a friend of a friend, stunning and just oozed sex. Jenny was 22, with a slim body and small, pert breasts. We started to meet regularly and spent more and more time together until one night we got off. It was a habit of mine, whenever seeing a girl, to ask about the things that turn them on and about their fantasies. Usually, they would be a little cagey at first, but after a little time and gentle persuasion, they would open up and reveal more about themselves. Over the weeks the talk became more dirty and the sex more filthy. It was so hot getting to hear about their little kinks. Like most guys, I especially liked fantasies that involved other girls. Whether I was in the fantasy or not, the thought of my girl eating another girl's pussy really turns me on.
We first met late summer after she had just come back from holiday in Ibiza. She had flawless golden tanned skin, blue eyes and long blonde hair. Her golden arms were long and slender as were her legs. After a few months, things were going well and she was pretty open-minded in the bedroom. I had quizzed her a number of times about her fantasies and she told me about how she used to masturbate in the garden shed using a trowel handle. She also, to my pleasure, had quite a few fantasies involving girls. I eventually drummed up the courage and proposed that she use a strap-on, that we reverse roles. This was make or break. Jenny may have ran off in disgust at the thought her boyfriend was gay.
"You can fuck me instead of me fucking you." I encouraged.
She went quiet for a while which kind of freaked me out, but eventually smiled, the giggled and said `Why not! '
Later that week, I went to a sex shop in SoHo, and found a great looking strap-on in black (somewhat embarrassing taking it to the till). However, I chickened out of bringing it out on so many occasions that I almost gave up. However, as is often the case, drink loosened my tongue. Jenny said that she had thought I was joking, but when I brought it out and she realised I wasn't, she was a little shocked. She took it out of the box, playing with it for a while, undressed and put it on. And, promptly burst into laughter. This made me feel very awkward and a annoyingly, it went back in the box. I thought that was that, but a few weeks later, a little drunk, she brought up the subject of the 'toy' and admitted that as she thought more about it, the more she was into the idea.
She teased me a little, asking if I was into guys. Having expected this I was ready with a reply that would not only place the female in the central role but also quash any doubts raised about my sexuality that may cross her mind. I told her that I got off on role-reversal and that it was being fucked by a girl not a guy that turned me on, adding that we should do it face to face so that I could see her, a girl, fucking me. Although true, I was being economical with the truth by not telling her that I was also into the idea of being fucked by a guy too.
At first, there is no denying that it was a little strange for both of us. As I got on my back and pulled my legs up to my chest, there was a bit of giggling as she fumbled around getting the dildo into position. Reaching down with my left hand I guided the tip of the strap on dildo to my arsehole.
"Now push a little, OK?" I instructed.
She did so adding that she could not believe she was about to fuck her boyfriend's bum with a strap on dildo.
I smiled and told her to push gently.
"Oh yeah, that 's it." I moaned at the pleasant sting in my arsehole as the prominent ridge of the fake cock popped in.
Sure, it was a little uncomfortable at first and there were a few misjudged strokes were she slipped back out of me, only adding to the awkwardness. However, she soon got into the swing of things and into a good rhythm. We were both getting into it and the dildo in my arse soon felt great. Looking at her thrusting into me, tits bobbing up and down was so fucking hot.
Jenny was now to fucking me good with the strap on. It was so horny being fucked up the arse with a fake cock whilst staring into a feminine face whilst feeling her pert tits. The strap on dildo lacked the warmth and throb of a real cock I would later get to know, but it stimulated my arse never-the-less. The prominent ridge of it fake knob end scraped up and down the walls of my arse in much the same way as a real cock would with the added bonus of playing with Jenny 's small, pert perky tits and tweaking her pointy nipples.
I am guessing that Jenny fucked me for about 15 minutes before the thrill of fucking her boyfriend up the arse coupled with the stimulation the textured pleasure pad of the dildo was giving her clit and labia made her cum. Her cute face scrunched up and her body shuddered as she orgasmed. Her small firm tits jiggled in my hands and the dildo buried in my arse wiggled from side to side as the orgasmic waves flowed through her body.
"That was wonderful, babe." I said as she collapsed on top of me.
She slowly kept pumping as I flexed and squeezed my arse on the fake cock.
"Mmm that feels so good." I said as my cock twitched and dribbled pre cum.
She started playing with my cock and said she now wanted me to cum whilst fucking me. Given how horny I was feeling, it wasn't long before she got what she asked for.
As she was still on top on me, my cum shot out and covered the both off us, our grinding smearing it over our sweat covered bodies.
After that first night we continued to play with our new toy and definitely looked forward to cock night. Once she realised how much I was into it she began to really enjoy taking my arse with her cock. Jenny was a hot girl and seeing her wearing a strap on was a real turn on. The more we played the more confident she became. With her cock she began to take more and more of a dominant role. One evening when we got back to her flat we started kissing, falling on to her bed. I pulled off her jeans and started licking her pussy through her white cotton panties. She moaned gently as I pressed my tongue firmly against the fabric. Teasing her, I continued to lightly lick her pussy as I pulled her panties to one side. After a few minutes she grabbed my head and pulled it down on to her now wet mound.
`Take my knickers off ', she ordered.
After doing so, she opened her legs wide. She bucked and moaned with an orgasm after ten minutes or so of my mouth stimulating her clit. We then switched positions. She reached down to her pussy, making her fingers slick with her own juices and proceeded to push her fingers into my arse. I moaned and arched my back up.
`I know what you would like right now '. She snickered.
After being instructed to close my eyes and sit up she went to the closet to get something. She came back after a minute and whispered for keep my eyes closed and to follow her instructions. I nodded in compliance. I felt her step onto the bed; she was straddling me and instructed me to open up my mouth. She then stuffed a black strap-on dildo into my mouth and ordered me to suck it. I opened my eyes and obeyed her command. I grabbed her firm bum, pulling her towards me, taking as much of the rubber cock in to my mouth as I could. Jenny said that she would `teach ' unaware that I had sucked plenty of cock. However, I played along and after what seemed like a while, which in reality was probably a ten minutes, my jaw starting to ache. I pulled my mouth from the fake cock, Jenny getting down off the bed.
She instructed me to lie back as she took a tube of lube the bed side table. She lubed a couple fingers and the strap-on before she inserted those fingers into arse taking her time to loosen up my sphincter. She then placed the head of her fake coke up to my opening and proceeded to push in at a slow constant rate and then pull back a little. She slowly pushed in the dildo inch by inch, pushing in a little bit further each time until my rectum had swallowed the full length of the black dildo. My dick that had gone half-mast at the time she inserted the strap-on, was now rock hard.
Now my arse was ready she started to increase her pace. Looking at her face I could clearly see how much she enjoying the strap-on rubbing on her clit as she pounded my hole.
She pronounced "I bet you would like the real thing up your tight hole" as she fucked me with authority now.
I held out for as long as I could but after she had took hold of my cock, that was it. My orgasm was unbelievable, cum covering my chest all the way up to my neck. Jenny scooped up some cum that had landed on my throat and stuck it in my mouth. She carried on fucking me and sent herself over the edge shortly thereafter.
We cleaned up and fell fast asleep.
Author – str8koklvr@gmail.com
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