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What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Trainer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny, Committed
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

Work Best Friend Finally or 61 is Great!

How long ago did this hookup happen? 2 weeks ago

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

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? My partner A is 61, blonde (dyed to hide grays at roots), 5’5″ with a long body and shorter length legs. Thin lips, perfect breasts that are round and not overly large but not small, firm. Wonderful neck to kiss. Hairless, no underarm hair, no bush near her vagina. Long, beautiful fingers. Having said that she is 61 so there are wrinkles, some flab on the stomach as there is with me at 52. Don’t think hot 22 year old here, but this is a beautiful, mature woman with a wonderful intellect.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A and I met just over 3 years ago when I took a new job. She is a co-worker but trained me on doing my job. We were cautious at first but quickly found we had a lot in common. We work very closely together and began to find out we had even more in common as we opened up to each other. A is a good listener as I am and as such over time, we shared some of the biggest challenges we have had. Her husband had betrayed her with porn and several affairs and she has gone through counseling which helped her, but she still struggles that he did that to her after 30 plus years of marriage. I shared that for 10 years I have not had sex with my wife or any woman because of the health conditions of my wife. It left me feeling untouched, unloved and horny at times. We take long walks at lunch together, talking about casual things, share similar political views, love science fiction and each have admitted we always feel a little pang of emptiness when it is time to go home.

We travel together, we eat together, we spend a lot of time together and know our weaknesses and our strengths very well. Work wise we are like a hand and glove and we have become that way in non-work settings. For the last year my emotional connection to her and my sexual desire for her has been ever growing, and in truth, by comments, she has made, her emotional connection to me and sexual desire for me is growing. One of our frustrations is sex. She loves it but since her husband’s affair, it is basically undress, kiss and french kiss for five or so minutes, he is hard, puts A into the missionary position, screws her until he comes, getting her somewhat turned on sexually, and leaves a mess in her without her having any orgasm. It is what she calls selfish sex and she hates it. To the point, she has cut him off.

Four weeks ago, A informed me she had decided she couldn’t have two men in her life, so we needed to cut back on sharing emotional things and just be professional at work. No problem. I had shared more at first because I needed to, her also. By now I had and she had begun to develop feelings, really deep feelings for each other and I felt it had scared her. I backed off. A week later she was asking me over to her desk six, eight times a day (we usually meet two or three times to go to work) to review the new Star Wars Trailer and info on it. On the third day, one time I put my hand down next to her mouse pad to watch and she slid her hand over mine. My interest in her movie clip was gone and the hook up began.

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? I looked at her and A smiled, rolled her eyes and said,”I have to have you in my life.” At that point, she pulled me down to the chair next to hers and reached over and kissed me. First a peck, and as I smiled she came back, kissing my lips as I returned it and her tongue eagerly seeking my tongue in my mouth.

We began to make out and I felt her hands on my thighs, move up and down on them, rubbing them. Instantly I felt myself getting hard and I began to rub her breasts. After fifteen minutes of making out and foreplay with clothes on, we stopped and she said, “Not here.” Our office is enclosed, securely locked so only ourselves, our boss who is 30 minutes away in another building and the janitors can get in there. We got up and A grabbed her purse and I told her “I’ll drive.” Not a male thing she just drives a Nissan Leaf and needs the electricity to get home. On the drive, I asked and she asked if we really wanted to do this. I told her that after 3 years I had a total crush on her and felt I was falling in love with her and I wanted her. I wanted to hold her, to watch TV and movies with her. To continue our long walks as she played Pokemon Go and to just be with her. I wanted to make love to her and not just once, over and over again. A looked and me and said, “I know I love you, and I know I want to have sex with you over and over again and I want you in my life.” We both agreed that we were not willing to leave our families for our affair, but this would be a long term on the side and if the opportunity ever came to commit we would.

We drove the 20 minutes to a Marriott and as I parked, A got the room. She met me at the door and we took the elevator up. In the elevator, we began to make out until the door open. A had always expressed she was not the openly affectionate person but she held my hand as we got to the room door. She opened it, led me in, shutting the door with her foot and we earnestly began to kiss and make out. Slowly we undressed, leaving a trail from the door entry way to the bed and by the bed, we were both naked,

We laid down on the bed and began to explore each other. Her long fingers walked down my long torso to my testicles and hard and fully erect penis and began to massage my testicles and slowly stroke my penis. I played with her breasts, feeling her nipples harden under my touch, and then worked my right hand down to her vaginal area. I began by gently rubbing her outer and inner labia and A responded to that. This continued for about fifteen minutes (A had explained the twice a month her husband made an appointment for sex, there was no foreplay and he basically got her in the missionary position, kissing her for five minutes, entering her vagina and in less than two minutes was ejaculating in her having his organism, leaving her often wanting more), and then I stopped fondling and caressing her breasts, moved to kissing her neck, kissing and gently sucking her breasts, and then kissing down her naval to her belly button.

From her belly button, I worked my way down and using my hands, spread her legs out enough to allow my mouth access to her vaginal area. Using my tongue instead of my finger I worked her vulva, her outer and inner labia with my tongue, slowly, rhythmically up and down turning A on. A began to breathe heavier, and I got several “Oh’s” from her. Slowly as her wetness increased, I worked up and found her clit hard and easily used my tongue to gently stimulate her clit. The tip and side of my tongue did their work and in five minutes, A was moaning and her butt moving in rhythm. I slowly increased the pace until suddenly A moaned loudly, got very loud and in a high pitch tone screamed “Yes!” several times as he butt raised her vaginal area up in the air and down and up and down three to four times.

A pulled me back up and instantly started kissing me as she guided my erect penis into her vaginal opening. I whispered “Sure?” and A replied “Hell yes!” and rammed my penis into her vagina. I slowly shoved it all the way in, I am not a long man at 7 inches but I do have 12 inches of girth and have never had a problem providing vaginal orgasm to a woman. I worked slowly at first, but steady, and slowly increase my pace. It felt SO GOOD to be in a woman and A was kissing me, her tongue in my mouth, her tongue on my neck and kissing my cheeks. I saw her chest grow pink and that pinkness spread up her breasts to her neck to her cheeks and then her entire face. By now I was going fast and steady in her and A  screamed out in pleasure.

I felt her kegel exercises pay off as she squeezed my penis with all her worth. I didn’t want to cum yet so I withdrew as she kept kissing me. I then moved A to be on top of me and had her guide my penis back inside her vagina after providing some gel to moisten her back up. A got wide eyed as I entered her and realized she was in control. I would shove upward but he was now moving up and down, back and forth, controlling our pace of lovemaking.

For the first ten minutes, A simply enjoyed making love and looking into my eyes as we held hands. She didn’t have to say it as her eyes did but she said “I love you” and I replied, “I love you too.” Slowly her pace quickened and I felt my penis swelling as it got ready to explode inside of A. A responded to my penis hardening and increased the pace and suddenly started to quickly, I mean quickly jam my penis in and out of her vagina (not all the way out but about 3/4 of the way) and began to moan. Her moan increased as her pace increased and suddenly she fell on top of my chest as I began to ejaculate in her vagina eight times as she squeezed and keep squeezing to milk every ounce of me to be inside of her.

We stayed like that, A gently moving my semi hard penis around inside her vagina. We kissed and agreed this was the best sex either of us had had. It was more than that too. As we talked the tension of the past year was released, and we shared what we liked and loved about each other. Slowly we began to playfully pet, touching each other again, arousing each other, enjoying each other and we had two more love making sessions where A had multiple orgasms and together, we shared one when I was ready to cum in her.

We both ended taking a day off of work as we had arrived at 10:00am and didn’t leave until 9:00pm that night. We had showered together at the end, thinking to clean up but made love in the shower and then showered as A gave me a blowjob and ended up swallowing what was left of my ejaculate by then.

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? Since the hookup, we have gone to our hotel 3 times a week and had what we call our bonding or intimate time or code work for spouses or work our development time (developing training). This week, A is on a vacation to be with her grandkids in California. She has sent me texts and emails to a private account and we have a room reserved for Monday afternoon and Wednesday all day when she returns.

The Friday before she left though, we had a deadline and so instead of the hotel, we ended up at work really late, 8 pm, no one, not even the janitorial staff was there so we ended up having sex in the office after completing our work. Fun! I had brought a sleeping bag air pad so we did it on her desk, on the floor with the air pad, and A wanted to try it doggie style from behind with her leaning over a chair and then her desk (she liked the desk better) as we made love. A actually found a new position she liked, but not as much as 1. being on top (her favorite now) 2. Missionary style or side by side, and 3. Doggie style leaning on her desk or a waist high table.

We have no expectations for the relationship, one thing A learned in counseling is to have low expectations so you are always content with what you have. Having said that, we plan to continue to have the affair, to keep it going for a long time and to enjoy it. A would leave her husband but fears the impact on her kids and grandkids. I cannot leave my wife. My wife only has a couple of years left and she has expressed that I find someone (I don’t think she thought I would find a woman 9 years older than me) to get my sexual and emotional needs fulfilled as she can’t but to never tell her. I continue to be with, to love and support my wife. That is vital to me and A understands that and supports it. So for now, we are co-workers, lovers, and friends and that is enough.

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, I was feeling lonely, It was easy / convenient

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, just A, my partner in it.

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? First, the sex is AMAZING! Find the right older woman and WOW! They know what they want, communicate what they want, will tell you if they don’t like something and will listen and do the same for you. The result is incredible sex. Feeling wanted, loved and touched was also amazing by this incredible woman.

What was the WORST thing about this hookup? I cheated on my wife. I have never cheated on my partner but after 10 years of illness, I needed to feel human, to feel connected. to have sex again and to love and be loved. So it was a tradeoff of needs, the need to be faithful in a most challenging circumstance, and the need for human connection to a woman, a lover, a friend, a companion again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. Wasn’t just a one night hook up, could have been but my partner A and I have a passion and commitment for each other. If she said stop, I would of course and be grateful for what we’ve shared. It won’t be happening though. For now, I just enjoy every moment I am with this beautiful and incredibly brilliant woman.

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 love when A and I now go to the hotel, or meet there and go up to our room. In the room, we can just be us. We still walk at lunch time together, we still talk and share and we are still highly successful at what we do for our employ. Besides the casual sex which is incredible, we remain dear friends, vested in each other and beyond just knowing we are lovers. Best of both worlds.

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? Casual sex is that casual sex and it has a place when you’re young. As you age you usually want more, at least I do. I am not one to cheat by nature and I prefer one commitment at a time. However, there are times need, want and pure desire takes over and sometimes one has to give into it. If you’re having multiple partner sex, protection is important. In our case, I have no sex outside of A, and A has cut off her husband now.

What do you think about the Casual Sex Project? Allows different people to see how a variety of people act toward casual sex.

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

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