by Lilly

Gender: Female
Age: 30
Race/ethnicity: Hispanic
Current location: Pennsylvania
Highest education received: Some college (not currently in college)
Occupation: Business Owner
Relationship status: Single
Religious affiliation: Faithful
How religious are you? A little
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 10+
How many hookup stories have you here posted before? 0

Lusting For Too Long

How long ago did this hookup happen? 3 Months Ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends With Benefits

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? He’s exactly my type, tall dark & handsome with a football player build. I’ve never been so attracted to a man’s ass before… Just makes you want to bite it… But he has a great sense of humor with a charming boyish smile & infectious laugh. Problem is we were coworkers… We became real good friends & I confided things in him. I had such a crush for over 2 yrs before anything happened but he was happily married & we worked together…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day he was giving me a ride home from work as him & his wife & kid were soon moving just a few blocks away from me. We always had great convo & that day I was complaining to him about the previous guy I had been hooking up with. Up to that point that guy had been the best I ever had but he came with drama. I was a little unsure of how much to say as we didn’t normally discuss sexual encounters etc. but I had fantasized about this guy for so long… And the other guy wasn’t pulling through on a hookup night, we were winding down to the end of us. Anyway, my crush kinda turned to me then back to the road & nonchalantly threw out there that he’d be willing to help me blow off some steam. I was like, really?!? Inside I was like wow is he FINALLY making a move…? So we made plans to hook up that Friday. He would pick me up & we’d go to a hotel…

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? The big night came & I was pretty nervous. I had fantasized about him for so long… Over 2 yrs of rubbing it out to this guy… I tried not to have my expectations to high but they kinda were, lol. I must have taken so many deep breaths before hand… I was completely sober & I never am before sex because I love to smoke first but I didn’t know how he’d feel about it. Be cool, no big deal, u’r a grown woman & this isn’t a stranger… I had to give myself a little pep talk in the bathroom first, lol. I had spent hrs getting ready making sure I was silky smooth & had just the right scents in all the right places… I was soft & fresh & smelled like candy… One last go for it & I walked out the bathroom & into the room. He was on the bed searching for background stuff on the tv when I came out. I was a little self conscious & hoped into the bed right away. He went into the bathroom for a sec then came out & I was like wow this is it… It’s really finally gonna happen… He walked over to the bed & got on top, my heart was beating so fast… I could feel his strong warm thigh in between mine, pushing them open as he kissed me. Even just kissing him all I could think of was FINALLY!! I was soaking wet by the time the kiss was over & now he was caressing me… His fingers working down to my pussy. He’s a big guy & everything’s big… His fingers in me… I’m tight & small… His member was… Very healthy, lol magnums were definitely needed. Everything after that was pretty much a desire filled blur… I pushed him off & he laid back comfortably while I settled myself between his thighs. I took him into my mouth as much as I could. Even this had been a fantasy for me, making him moan & feeling him loosing control. He was so big & warm & hard throbbing in my mouth like steel wrapped in velvet. I don’t remember if he went down on me that first night but I can’t forget how he felt inside me. He was much bigger than the last guy. He stretched me & filled me & when he was all the way in I could feel him in the back of me so deep rubbing that spot that felt like it was at the core of me…. Because I hadn’t puffed first & he was so big it hurt a little but it was glorious. The feel of this man who I had lusted after for so long finally fucking me had me spiraling out of control… I couldn’t bare it every time he pulled out a little. I wanted to claw him & devour him… He was driving me crazy!!! I think that first night was when we did anal as well & that’s not something I normally do. Love the idea of it but the reality of it can be painful. Yet here I was face down on the bed with this massive guy sticking his huge cock into me, his fingers laced into mine his warm breath on my neck & his light moaning in my ear… When he came he it was almost like a cheer full of satisfaction & surprise… I thoroughly enjoyed it… 3 hrs later we got dressed & ready to leave the hotel room & he had made me thoroughly SOAK THE BED… That was our beginning… Expectations fulfilled… No way was I giving him up. We continued & even tried bringing his wife into it briefly though she had no idea the full extent of our intimacy… But as she had been with a woman in her past we tried to turn it into a group thing but that didn’t work out well. We all fooled around one night & she ate me & watched us fuck each other but then didn’t handle it so well… But that’s another story for another time… So we continued on just the 2 of us…

Did you have an orgasm? Did your partner(s)? We both definitely orgasmed. I soak the bed every time he fucks me. My only disappointment is that he doesn’t cum in me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We knew each other very well. He had been monogamous with his wife before me & I was always cautious in choosing partners. We used condoms at first but don’t anymore. We all got screenings done him, his wife & myself before she joined us. He pulls out though I’m dying for him to cum in me. I’m not on birth control but not sure I can even get prego. If I can it won’t be easy…

What were your REASONS for having this hookup? We always had these sexual undercurrents but as we worked together we were reluctant to start something. But 2 months after we started, I left the job to open up my own business so that’s not a problem either.

Were alcohol or drugs involved? If so, how much? We puff together beforehand now but on our first night we were both sober….

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Afterwards he drove me home. We were both happy with it as we continued hooking up… We’re committed to fulfilling each others fantasies. Unfortunately, I’m falling for this guy I can never really have… I have respect that he has a family & I’m not trynna break that up. But he is now the best I’ve ever had & after like I said over 2 yrs of fantasizing about this guy & having my fantasies about him come true, I just can’t give him up yet…

To whom did you talk about the hookup? How did they react? My 2 best friends know. The female one was supportive & the male one is supportive of me though he doesn’t completely approve only because the guy is married…

Was this a consensual and/or wanted experience for you? For your partner? Consensual for both parties

Do you regret this hookup? If so, why? Yes & no…  Only no because I now know exactly what I’ll be missing on the long term end. Things can’t last forever, he is married. But I’m determined to enjoy him as long as I can…

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing is him. He’s the best I’ve had sexually & so my type physically in every way. The worst is that it won’t be more than hookups… As far as my thinking goes, I think when we’re over I’ll be more sexually confident in starting something with the nxt guy instead of just being sexually confident when we’re already well into hooking up. I know I’m not a dud in bed, I’m very passionate & have never had any complaints I’ve just also been very shy & so have always let the guy take the lead…

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

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

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