More Risky Cheating 2



What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK North west
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Promiscuous
How many sexual partners have you had in your life (including oral sex)? 50 – 100
How many hookup stories have you here posted before? 4

More Risky cheating 2

How long ago did this hookup happen? 10 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? D was a neighbour and a student. Quite a bit younger than myself. She had an amazing figure and short dark hair. I used to own an apartment in Liverpool City Centre, where I lived with my girlfriend S. We had been there a year or so when D moved into the flat above us. We probably wouldn’t have even met each other but for the fact she used to annoy the hell out of Sarah and I, so much so that I had to go up stairs to knock on her door a few times when the music got too much. It was always so loud coming through the wooden floors. She’d have friends round and go out on the town a lot, like students do, and walk around her place in heels. We had a large open plan living room with tall ceilings and the sound really seemed to carry. It was so bad one Friday night, and I was in no mood for it having driven a long way to get home, that I had to go and say something. Any confrontational attitude evaporated when she opened her door. She was super-hot, but clearly a bit worried about having a total stranger knock on her door on a Friday night. She was getting ready for a night on the town and had on some pyjamas and a vest top. I softened up immediately, took a more friendly approach and introduced myself, explaining that we lived downstairs below her. In honesty the music wasn’t at all loud, but just travelled through the floor. In any case she was very apologetic, even a bit flirty, which I loved. I cheated on my girlfriend a hell of a lot back then, and would actively be on the lookout for any kind of attraction, and there was definitely some here. She asked me to let her know anytime if anything was annoying us downstairs, and I left hoping that meant she’d like me to come knocking again, as I sure wanted an excuse to soon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was home the following weekend, and hadn’t given a lot of thought to D. I had been away all week in the south of England where I was based. I had gotten to thinking about D again on the long drive home, as I hadn’t managed to get any sex during the week. S and I were woken at about 3 am the following morning by a few people noisily staggering into the flat upstairs. Hoping it would calm down we lay there for a while, then the music came on, so I threw some pants on and hastily ran up the stairs. It took a few knocks to get an answer, and I heard some panicked and very drunken whispering as the music suddenly lowered, and the door opened. Its always a struggle to communicate with very drunk people when you are sober, but I eventually got my point across despite some very inappropriate comments about playing loud music more often (I was tempted to start flirting back with D and her drunk friends, but was still testing the water) It was music to my ears when D offered me her mobile number to save me having to come upstairs all the time. If I didn’t want to fuck her, I’d have suggested that she just stop giving me cause to come upstairs but I wanted to get back up here at every opportunity. She was hammered and I was taking advantage. She looked stunning in a black dress, and I suddenly noticed a very pert pair of tits and a great arse. I declined the invitation to come in for a drink, despite every sinew of me wanting to, and returned to bed very aroused at having her number. I didn’t tell S I had her number, but let her know that I had been assured it wouldn’t happen in future.
I had a secret mobile and used that to start some innocent dialogue with D a week later. I had a couple of weeks off work and had nipped out with a neighbour friend to watch a game of football at the pub around the corner. I took my secret mobile and sent a tentative text thanking her for coming in quietly the night before – I knew she had been out. She replied jokingly that she had been tempted to get the music on to get me back up the stairs in my pyjamas… I suddenly got that very warm feeling you get when you know it’s likely you are going to fuck someone you have been fantasising about. I downplayed how I must have looked at that time in the morning, and she took the bait, commenting on how much her friends had talked about her and egged her on after I had left. I let her know that I had been tempted to join them, but my girlfriend would not have approved. I had no idea what was happening with Liverpool on the TV as the flirting continued. After a couple more pints of beer and my cock now doing all the thinking for me I suggested that she play some very loud music whilst she was getting ready later. Her response was that she was at home and ‘getting ready’ right now. ‘where are you..? are you home..?’ she asked. ‘should I put some music on..?’ ‘I’m not far away. But if I come up now the we might have to put the music on to suppress other noises..’
And so the floodgates opened and we were now telling each other what we had secretly been wanting to do to each other this whole time. She told me she wanted my cock inside her, I told her I wanted her pussy on my mouth. Tonight. I was practically ignoring my friend now, but he was engrossed with the match. The game was practically over. I had a valid reason to leave.
‘Shall I come up and see you ?’ ‘Yes. Right now. Isn’t your girlfriend in ?!’ S would be getting ready, we were going out later too for a friends’ Birthday. ‘Yeah, she will have her own music on !’

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? My heart was pounding and my cock was throbbing as we left the bar. I text D that I would be there in 10 minutes. My friend and I went our separate ways at the entrance, and I crept up the stairs past my landing and up the next flight as quietly as I could, hoping not to see anyone. Rather than knock, I text D again to let her know I was at the door. She opened it up and ushered me in. I barely had chance to notice she was wearing just a t-shirt and a thong. She pinned me against a wall and started kissing me. Our hands were all over each other as we kissed. I knew S would be getting ready, basically a few feet below where we were stood. Before I knew it she was squatting in front of me pulling my jeans and pants down to me knees. My rock hard cock sprang out in front of her face oozing pre-cum. I was so excited and had been for hours now. Weeks even, if I thought about it. But all I was thinking about now was how wrong this situation was but how fucking good it felt, watching D lick and suck on my cock, looking up at me to see the ecstasy I was in. We hadn’t said a word to each other since I walked in. I had to stop her else I would have cum. I pulled her up and lifted off her t-shirt. Her tits were pert but so soft. I licked and sucked hungrily on her nipples and began to rub her clit gently through her tiny thong. She started to breathe heavily in my ear and I guided a finger inside her soaking wet pussy. I gently kicked off my shoes and pants and walked her over to her sofa quietly. I positioned her kneeling on the sofa with her arms on the head rest. I pulled off her thong hastily. She was naked now. She pushed her arse out invitingly and I started to lick her out from behind, kneeling on the floor behind her. She pushed back onto my face as I licked at her pussy and arsehole in turn. I could have stayed there all day. She started grinding slowly on my face, pushing gradually harder and faster until she came, muffling a load moan of pleasure into the sofa cushion.
I stood up behind her and pushed the end of my cock against her cunt. I loved that view you only get from fucking a girl from behind and especially when it was that first moment of penetration and with a brand new pussy. I had to hold back a lot as I started to fuck her, I didn’t want to cum just yet. Her young body looked amazing and every time I slowed down she would just take over and push back on to my cock harder and faster. I felt myself start to cum and pulled out initially to try and stop myself but D had sensed I was reaching climax and used one hand to spread an arse cheek inviting me to splash my cum on her from behind. Wow, she was good. I shot I big load over her back and arse, ensuring that I shot some over her arsehole.
As usual, that moment of clarity hit me, and I realised the situation I was in. The pangs of guilt set in, but did not last. D was rubbing my cum into her arsehole and all over her cheeks. I noticed a gap in the curtains to my left and realised that she had the same view of the communal gardens as we did below, and thought that she could have looked out and seen me fucking a girl on the bench out there a couple of months before ! (another story I posted on heres)

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? It was a crazy turn on creeping back downstairs and letting myself back into the flat. We fucked again a few times before D moved out, and had a lot of fun texting each other and taking risks. Not seen her again since she moved out.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told a military friend and he didn’t believe me !

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? the risk, being in such close vicinity.

What was the WORST thing about this hookup? Wondering whether we might get caught !

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was a different person at the time. I have grown up since! But I was totally addicted to the feeling of fucking new women, although the cheating and the risk added to it.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? Great way to share, and re-live my sexploits

You have a hookup story to share? Submit it here!