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What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA, Rocky Mountains
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Small Business Owner
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? None
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 2

Warming Up From Shoveling Snow

How long ago did this hookup happen? It started 2 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 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 in her mid-forties, mother of 3, two are in their early 20’s, and one is in high school. She works part-time and is 5’4″, thin, with a nice, round butt. You can tell she gave birth to 4 kids (one died after birth). She is blonde with hair down to right above her small waist, has blue eyes, and she exercises daily and eats very healthy, trying to preserve her figure. She has only had sex with her husband, and she was a virgin for her wedding night.

Ali is our neighbor; I met her when I moved into my house about 12 years ago. I know her very well, and she is a friend. I know her husband also, not as well as I know Ali because he travels a lot for business. We both own successful businesses, and we talk about them from time to time.

Ali will catch my eye as I see her across the street in our cul de sac. In the spring and summer, she likes to work outside in shorts and t-shirts that show off her large breasts, and I enjoy watching her. As with any man, I have had the fleeting thought that it would be fun to mess around with Ali, but that has been all it ever has been as I have always thought that Ali was firmly devoted to her husband and family.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?

It snows where we live in the winter, often heavily and on this morning it had snowed a good 12 inches outside. I got up, dressed, and began to snow blow my driveway. It only takes me 20 minutes or so to do my own house, so I usually help a couple of my older neighbors with theirs when I am done.

As I finished with the last neighbor, who lived two houses down from Ali, I saw that Ali was out by herself snow shoveling. Her husband was out of town, and her son had gone to school. I took my snowblower down and started on the opposite end of Ali’s driveway, and she waved and smiled at me as I went by her. Ali has a large driveway, and she got about 1/4 of it done by hand, and I did the other 3/4. I shut off the machine at the end, and Ali walked over and thanked me. I was sweating a little, and I could see that Ali was warm by her rosy cheeks and some perspiration on her forehead.

Ali asked me, as she often did if her husband wasn’t home if I could help her move a couple of pieces of furniture around as she had just re-done and re-finished (that is what she did for her own hobby/business). “Not a problem,” I replied. We entered the house and removed our snow boots and coats, but I left on my snow pants as I didn’t have anything but my boxers on underneath. Ali led me down the stairs to the finished basement.

“I need to move the bed out a little and then move the nightstand in and then re-center the bed,” Ali explained. “The king size is too large for me to move around by myself.” “No problem,” I said and moved to the right side of the bed, while Ali took the left side. We moved the bed out and then I brought the nightstand in, moving it to its position. We then moved the bed back and used two attempts to center the bed in the room. Ali stood about 3 feet from the bed’s end trying to determine if it was centered. “Dave, come help me see if it is centered,” Ali asked and kinda of ordered. “Okay” was my reply and I moved and stood next to her.

The bed to me looked centered, and I said “Looks good to me” to which Ali turned to me and asked, “Do I look good to you?” That shocked me, and I answered truthfully “Ali your beautiful and Ken (her husband) is a lucky man.” “You think so?” Ali replied. “Yes, you’re gorgeous.” I noticed her hair was in a long braid falling to her waist in the back, and for the first time, I noticed her nipples were hard. Ali moved closer to me and said “I need to thank you for always being here to help me. I need your help some more.” With that, she wrapped her arms around my neck, and we she reached up and kissed me.

I didn’t know or even guess she had romantic or sexual intent toward me at all. She was always friendly and I the same to her, but at this point, I didn’t care. My wife had slept with two men in our marriage, one at a work function because he was drunk and the other partner was a fuck buddy for when she wanted variety. I had had a FWB at one point and found that it enhanced our married sex life until she was transferred for work. If Ali wanted to get laid, even just once, I was happy to help her out as a friend.

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?

Her lips crushed onto mine with some strength and force and then I felt her tongue on my lips as I opened my mouth. As we made out, Ali undid the suspenders on my snow pants, pulling them off my shoulders. They fell past my waist as I removed my merino wool sweater and then the fleece shirt underneath. I am in decent shape for being my age, and she now ran her hands on my bare chest.

I moved to say something and Ali brought her index finger to my lips and said “Shh.” She then kept kissing me. I now returned the favor and lifted her shirt off her upper body, exposing her sports bra which I quickly removed. There I saw her beautiful round breasts with two hard and erect nipples. We continued to make out, and Ali kept rubbing my chest, and with one hand I fondled and caressed her boobs and nipples. For the next ten minutes we made out and felt each other’s torsos, and I could tell that Ali was turned on.

Ali had removed her snow pants and was wearing athletic pants underneath. I now bent down and removed them and her underwear and socks. I laid Ali on the edge of the king bed, and she propped herself with some pillows from the middle.

Ali’s legs are to die for: long and firm. I began to kiss up starting on her foot, going to her ankle and calf, then up to her thigh. I saw that she trimmed her pubic hair into a nice V shape as I kissed up her inner thigh and she sighed when my lips came in contact with her outer labia. They were rather large and the moment I kissed them, Ali, moaned “Oh, Oh,”  I licked and kissed this area for a good three minutes, and Ali moaned again and said: “Keep going.” I did just that and now moved to her vaginal opening which was soaking, and I enjoyed tasting her cum and wetness. Her hands now moved to my head, and she gently but firmly pressured my head into her vagina, I inserted my tongue and licked backward. Ali’s breathing began to quicken, and I got a lot more “Oh, Oh, yes, yes, YES!” as I kept licking and thrusting with my tongue.

Ali suddenly squeezed her thighs together around my head and lifted up in the air, once, twice, three, and on the fourth time she screamed: “YES, YES, OH YES!” I felt her squirt hit my chest, and then a second follow up before Ali collapsed under me.

For a good two minutes, Ali laid in the throes of her orgasm to which I got up, removed my snow pants and boxers and my socks. My penis was hard as a rock and I it stood straight out. Ali saw it, and I told her to move up to the bed. Once at the top, she put the pillows behind her so she was at a 45-degree angle and her legs were bent at the knees at her side. “That was awesome,” Ali said. I asked her “You’ve never had oral sex before?” “No,” Ali said, “But I think I’ll be getting more of that from you again!” Then Ali looked at me and motioned for me to come to her with her index finger.

I moved up the bed, and came to her, my legs now parting hers as we began to make out again. I started to rub my hard penis against her vagina, and I could tell Ali was super soaked and ready for me. She was holding me close to her again, and then one arm guided down in between our bodies and grabbed my penis and moved it inside of her.

I drove myself entirely inside of her and held myself there. Ali’s eyes widened, and she pulled me closer, her breasts pushing against my chest. I began to play with one breast as I partially withdrew and then pushed slowly back inside of Ali completely. Back and forth we went slowly at first and then build our rhythm up. Ali was enjoying it, moaning and breathing heavily. I brought her close to orgasm and then withdrew my penis completely. “Hey!” Ali looked at me. “Get it in there.” I smiled, and I moved unto my back and moved Ali on top. “Ever been on top?” I asked. “No, Ken only does the one position.” “You’ll like this I said.”

Ali then eagerly guided my hard penis back inside of her vagina without help. I thrust the first time upward and then she figured out she was in control. She began to push my dick completely in and then partially out of her. She varied from going fast and hard, to slow and easy. I started using both hands now to caress her beautiful round breasts which turned her on more. Ali slowed down and then stopped with my penis completely inside of her. I thrust my dick now up deeper into her and back down an inch or so and back in. She leaned forward and started to push me in and out, over and over again. I started thrusting as Ali now fell onto my chest and began to kiss me hard and fast, her tongue matching my movements inside of her. Her body went pink then red as her flush hit, and I knew she was close, and so was I.

I felt her tense several times and then relax as her orgasms released her. I couldn’t hold back and didn’t want to, and as Ali exploded into ecstasy, I shot my first load deep into her. That made Ali scream, and I ejaculated four times into her, and then probably five or six minor ejaculations.

Ali kept squeezing my penis as she kissed me, laying on my chest now. I kept thrusting my penis inside of her, deeper and deeper each time I came in her. “Did you like that?” I asked. “Yes, oh Yes.” Ali kissed me passionately and then staring at me “I never knew sex could be so good.” I smiled thrusting my penis back deep into her vagina, and Ali smiled “I like that a LOT!” “Want more?” I asked. Ali smiled and said, “How much more can you do?” “Give me 30 minutes, and we can go again. Can you kiss me, talk and enjoy for 30 minutes.” Ali looked and said, “So 45 minutes to make love, 30-minute break, that means we can do this three more times before my son is home from school!” I had moved off of her now, withdrawing my semi-firm penis from her vagina and laying at her side. “Sounds great to me!” I replied.

We kissed and made out and talked. I found out that her husband Ken was not a romantic. He expected Ali to lay there three times a week when he was home while he mounted her missionary style and in 3 minutes had ejaculated in her. Ali never really experienced the orgasms she had with me. We made love again, this time I had her stand and lean over a comfortable chair while she guided my penis into her vagina with her hand as I did her from behind. We enjoyed that, but after five minutes we were back in the bed, Ali on top. She had found her position, and I wasn’t going to argue. We made love with her on top and climaxed in that position again. Next, after recovering we did the missionary position again, and then one last time with her top. We ended taking a shower together, and she sat on one of the large seats in the shower, spreading her legs up high as I made love to her for the last time that day. I left about 10 minutes before her son came home and I was exhausted. Ali said she was feeling great and wanted to see me the next morning again but this time at my house in my bed.

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? This was two years ago, and Ali and I are first and foremost great friends. If something happened to our spouses, we’d marry each other in a minute, but we won’t let our hook up ruin our families or kids. So we keep it private. For the next four weeks after the first hook up Ali and I made love each day, Monday through Friday, sometimes just once due to work and sometimes I took the day off and we’d have what Ali calls the Ultimate Marathon.” Ali just came over about 10 minutes ago and corrected a few things. Now as I finish we are going to go make love for an “Ultimate Marathon” since we have no kids at home, our spouses are traveling for work, and so we have each other to fill the day and night with a hell of a lot of fun and sexual enjoyment.

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), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Just happened, I don’t know why, just went along with it

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? Only each other. Loose lips end fun.

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? Making love to Ali and hooking up with her is incredible. My wife is excellent in bed and Ali is also. I am a lucky man to have two beautiful women in my life. Also the fact that I helped Ali discover that she can take and have pleasure from sex, and her partner should be as concerned for her desires as for their own.

What was the WORST thing about this hookup? Ali’s husband still demands sex the two weeks a month he is home and she may as well be a sex doll. Several times she has called me and we have gone to a local hotel for an hour after her husband is done her and we make love just so she can have an orgasm.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Far more open about having my wife and Ali. I told my wife about a year ago since we are open and she thought it was wild! Ali and I and my wife have done a couple of threesomes and I’ll have to share about that hook up sometime. I LOVE those! I get worn out quicker than the women but its fun to bring multiple women to orgasm multiple times in a night.

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

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

Anything else you want to add about this hookup? Glad we are still hooking up.

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? Whatever rocks your boat. Find out what works for you and do that.

What do you think about the Casual Sex Project? Expanding attitudes.

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