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What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Western US with Desert and Mountains
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professor
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Give pleasure before gaining pleasure
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Mild, Warm, Hot, Hotter, HOTTEST

How long ago did this hookup happen? 1 week ago

What was your relationship status at the time? Engaged/Married (open)

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For 1 to 3 years

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? Ali is 5 foot 7 seven, long blonde hair down to between her shoulder blades, blue, blue eyes, slim figure with smaller size breasts. Long, LONG legs with a beautiful smile, a confident walk or gait, depending what she wants to display, and very intelligent.

I met her conducting training at her school for teachers under 3 years experience, she has 2, and then she signed up for taking an endorsement through her school district connected to the university I work at. She took classes from me, and twice a week came to my office hours with a couple of excellent questions, but then to hang out.

Ali is very good looking, very attractive, newly married and VERY young at age 25 compared to my 47. Technically, I biologically could be her father. So though I noticed her as good looking and as most men do, had the fleeting thought I’d like to spend a night with her fucking her brains out, it was only a momentary thought that I easily dismissed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? By the end of the first semester, my thick skull had figured out that this woman was interested in me. I was not sure why, but what the hell. I began to visit more and more with her at my office with the door open. One day, Ali arrived and I noticed she was wearing a rather short black skirt for her with a green button up blouse. She stood and asked me her questions, then turned, showing her firm ass and shut the door. “I want some privacy if that is okay?” Ali asked. “Sure” I replied as she sat down across from me. She crossed her legs and I easily could see she wasn’t wearing underwear and my dick began to grow hard. I could also see her pussy was completely shaven and her skin around her love area was slightly darker in color from her thighs and legs.

“Jim, what happens after six months of marriage and your husband cums in you after five minutes every time?” Ali asked. Looking at me she said, “I mean, I have a right to fucking know what an orgasm is, don’t I?” “Damn, I shouldn’t have been a virgin on our wedding night.” I was hard now, and Ali could see the bulge in my tan pants. She now stood, took my hands, and raised me up. Looking at me, she asked “I bet you know how to please a girl.” and then Ali kissed me. I kissed her back, our tongues darting back and forth in our mouths.

Ali now told me not here, she didn’t want to get in trouble with her employer or me with mine. “My husband is out of town for two weeks. Can you drive me to my apartment?” Instantly I grabbed my keys, leaving everything else, went out with Ali locking my door and walked with her to my car. We drove to her apartment, as I drove she scooted over and her left hand began to rub my balls. It took 25 minutes to get to her apartment complex which was nice, and we walked up a flight of stairs to the second level and to her apartment. Ali had told me she had been planning on fucking me for four months and just now got the nerve to do it, especially with her husband gone.

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? As we entered, Ali threw her purse and bag from school on the couch, took my hand and led me back to the master bedroom. There were candles in there that she lit, telling me she had put them out that morning. “Confident I would come eh?” “You’re fucking dumb, if you don’t aren’t you?” Ali asked me if her age, 25 bothered me since she knew I had a daughter 24 and two sons, 22 and 20. “Does it bother you?” “Hell no!” came the reply and she walked to me, having removed her shoes, and I had slipped mine off, and my socks, as I sat on the edge of the bed. Ali lifted me up, and said “No more talk” and her hands swiftly undid my belt, my button on the top of my pants and my zipper. I removed her skirt, and admired her slender figure and felt her moist pussy. She smiled and undid my shirt and then I undid hers removing it.

There we stood naked, my dick now fully erect as her long fingers grabbed it and curled around it. We kissed as we went to the bed and laid side by side. Her slender, long fingers played with my balls and my dick, turning me on as we kissed, My hand played and squeezed gently her left boob, which as I said, withwasn’t big or huge, just small, round and enough to fill my mouth. As I sucked her boob and her nipple, my hand worked its way down to her vagina area. I felt her pussy lips and started to massage them tenderly. Ali was now dripping with pussy cum as I continued to work her. I slowly went up to her clit, and just rubbing the side, found her magic spot.

Ali moaned as I discovered it and I played with it. I went down with my mouth and using my lip I stimulated her clit even more. I inserted first one finger into her vagina, and found her g-spot and then brought a second finger to bear as she continued to be sopped with cum. I brought used my tongue and fingers and gave Ali her first multiple clit and vaginal orgasm of her young life as she held my head down in her pussy area with her two hands, and began to groan loudly in pleasure.

After her convulsions ended, I came up and laid side by side with her. Ali said, “Shit, that was incredible!” “Just wait, there’s more of that” I replied. Ali’s right hand and fingers now grabbed my cock and began to stroke it. I let her do this for a couple of minutes as I kept fingering her pussy. I then stopped the foreplay, lifting her leg over my hip and taking her hand with mine, and grabbing my dick together, I showed her how to guide my engrossed dick to her vaginal opening.

As my dick came to her pussy hole, I pushed my data leisurely pace into her pussy until the base of my dick was touching her vagina. As my dick filled her cunt completely, Ali whimpered quietly in pleasure. I began to move my dick about half way out and then all the way in, and each time I nudge my dick fully into her cunt, Ali would let out several “oohs” and “yes” or “yeah” and as I withdrew, I would get a few “ahhs” and a sigh.

I kept up a steady rhythm as we fucked, and her blue eyes would look at me and then close as pleasure filled her up. For thirty minutes I would increase the rhythm, slow it up if I felt my cum filling my dick, and then pick it up when I was ready to give her more. This build up led Ali’s nipples to become erect and because we were facing I could kiss them from time to time and play with them. I noticed that Ali was now matching my pace, drawing my dick inside of her, pushing it about 3/4 of the way out, and then pulling it back in. I saw her neck blush, and that fled up her neck to her face and I knew she was getting close. I now began to drive my dick with quick motions deep in her and suddenly she drove my dick in and out faster and faster, until she loudly said “FUCK ME NOW!!!!” I felt her pussy begin to convulse and send waves after waves of orgasm over her and she instinctively began squeezing my dick with her pussy. I erupted, shooting ejaculate inside that tight, wonderful pussy.

Ali held me now as I kept cumming inside of her, and kissing me. She looked at the clock as we laid on the bed, my dick inside her still, she slowly moving it around in her. “Fifty minutes. That was incredible! THAT is what I want sex to be like!” Then it hit her as she felt my dick squirt again, sending some more sperm into her vagina. Her eyes got wide and she said “We didn’t use condom! Oh shit! What if I get pregnant?” and I could tell that for an instant she was really concern.

I shrug my shoulders and simply said “But wasn’t it fucking worth it?” Ali smiled and said, “Totally.” Then I told her, don’t worry, after my last kid I had a vasectomy so if you get pregnant it won’t be from me.” Ali smiled and then with my dick semi hard still, she went down and began to try to give me a blow job by ramming it in and out of her mouth. I stopped her and laid on my back and taught her how to give me a blow job. Use the tip of your tongue on the tip of my dick, and right above the hole on the end of my dick. Work that over for several minutes, then lick the top of the head of my dick. Now as the dick gets hard, put just the head into your mouth, still using your tongue. Do that until I am fully hard and now we can either stop and fuck, or you can put it down your mouth. Ali is extremely smart, picked up on it and soon as I really hard again.

As Ali worked on giving me her first really good blow job, I moved her around and got into a 69 position and began to work her lips, her g spot, and her clit. After about fifteen minutes of stimulation, Ali again had multiple orgasms and I ejaculated in Ali’s mouth as she swallowed and then took it out of her mouth and as I kept cumming she had it shoot on her tits. She milked my dick and then licked it as I dribbled.

Ali now got on top of me, and again started giving me a blow job. My dick responded as I fingered her, keeping her juicy. About twenty minutes later after more foreplay, Ali still on top of me, put my hard dick inside of her soaked cunt and began to fuck me. Now Ali controlled the pacing the thrusting of my dick inside of her. Her pace quickened and several times I slowed her down so we could enjoy just fucking each other.

We built up to Ali having vaginal orgasms again as I shot my wad, my cum, inside of her. She fell on top of me and I kept ejaculating again, as she squeezed and milked it and we kissed. Damn, I love kissing this woman. Her tongue was silk in my mouth, and intermingled with mine so easily. Now we laid side my side, talking, kissing, and being naked. We touched, I rubbed her back, ran my hands down the side of her torso, played with her hair. She did similar things to me.

I ended up spending the night and making love two more times and then once in the morning. We showered and in the shower I taught her how to fuck doggy style to get an orgasm by me getting hard, and before inserting my dick, having her rub her clit on my dick. Ali took to this like a fish to water and soon she was squirting and then I entered her and fucked with her. I noticed she was so hungry to be loved, to be shown how to fuck with passion. We ended up deciding that we are friends, but as Ali said “Your my fucking benefit and I want you use that benefit as often as I can each week!”

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? I came back the next three nights for an encore and found that though we are 22 years different, this woman knows what she wants, knows who she wants it from, and is fine with my age. It is the experience she is treasuring and so am I. We ended up fucking at my RV three times this week and probably once more in the morning. It will be harder when she starts back to teaching in the fall, we’ll move to a quickie before school Ali says and stuff afterwards.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, give her experience

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? No one.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Fucking someone young again who is inexperience and I can show how we learn what turns them on and for them to learn what it means to turn me on. So communication. The VERY best thing was feeling her tight, cool, light skin against my olive warm skin and feeling my dick enter a very tight pussy again. So much!

What was the WORST thing about this hookup? None

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me rethink fucking someone in their mid to late twenties when I am in my late forties. No problem with that and Ali told me that if someone has an age issue, fuck them. We like the friends with benefits and often benefits.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I just love hanging out and fucking her! Her with me also. We are learning that besides sex, in many other ways we expand each others horizons.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Like I said, I use to think 35 was my minimum. Now, 25. Nothing wrong with casual sex

What do you think about the Casual Sex Project? Love it!

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

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