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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? Sant Fe, New Mexico
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Realtor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 0

She Gets By With A Little Help From Her Friend

How long ago did this hookup happen? Still Happening

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 less than a year

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? Emily is a beautiful middle-aged Hispanic woman. She is happily married but has a complicated sex life. Her husband Robert is also a friend of mine. I have known them from my work as a realtor and like both of them very much.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I like to stay in touch with all of my past clients because I need to network as a Realtor. I ran into Robert while shopping and asked if he and Emily would like to go to lunch the next day. They accepted my invitation and we met for lunch to just chat and catch up.
As we talked the subject of Robert’s health came up. He is diabetic and is struggling to stay healthy. We talked freely and openly because we are comfortable with each others company. Robert disclosed that he can’t keep up with Emily anymore because she is a bundle of energy. He also said quite matter of factly that he has had ED issues for the past year or so and that he has tried everything his Doctor has prescribed to no positive effect. Emily was holding his hand as he disclosed the situation to me.
I didn’t know what to say except that I understood how hard things are for him and I wished he could find something that would work for him. At that moment there was an awkward pause as they looked at each other while still holding hands. I squirmed a little but was relieved to see our waitress arrive with the check. I quickly grabbed it and insisted it was mine to take as I had been the one to ask them to lunch. Robert said fine but asked if I would care to walk around the corner with them to get a drink. Robert can’t have any alcohol but Emily wanted to get a Margarita. It was a Friday afternoon and I was ready to call it a week so I said sure.
After settling in at the Bar, Robert pointed out how beautiful Emily was in her outfit and how lucky he was to have her. I agreed. Emily did look great in her blue sundress. She has a beautiful complexion and such smooth skin and a killer body. She is definitely what I would call a HotWife. Robert wasn’t going to beat around the bush any longer so he asked me outright if I would be willing to help him and Emily out with their problem. I kinda blushed and half laughed that I would love to help them in any way that I could. At that moment the three of us set in motion a series of events that I never could have imagined. I was chosen by both of them to be Emily’s surrogate lover.
I am happily married to a beautiful woman that I love dearly. In our younger days, we had done some swinging and enjoyed the free love lifestyle. Kids came along and so did more work responsibilities so we let the lifestyle slip away. With the kids away at College, I have wanted to check out the swinging scene again but my wife isn’t into it any longer. I have always been a very sexual person and thought what the hell, let’s give this a try with Robert and Emily. My only rule is I will not play when my wife is in town. My wife does travel quite a bit with her job so I have plenty of opportunities to play if I choose. So it was decided we would meet at their house the next Thursday evening.

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 arrived at Robert and Emily’s home a bit nervous but happy I had made the trip. Robert let me in while Emily was just getting out of the shower. Robert fixed me a drink and we were chatting casually when Emily walked in wearing a silk bathrobe. She looked amazing! I noticed her nipples were showing through her robe. I started to feel myself getting a little aroused. Emily must have had her radar on because she brushed by me to get a drink and casually ran the back of her hand across my crotch. She smelled wonderful and I almost reached out to caress her ass but checked myself from doing so.
We went to the family room and I sat down on the couch while Robert took a seat in the recliner. Emily followed us in and sat down beside me. Robert began by thanking me for coming over and being such a great guy. Emily put her hand on my thigh and said how happy they were to have me as a friend. My heart was pounding and I knew at that moment I was going to do whatever they asked of me.
Robert was so cool when he said I was free to do anything with Emily that she desired. It was all about Emily and her needs. I agreed that Emily’s wishes were all that mattered. No sooner were those words out of my mouth when Emily leaned to me and kissed me on the cheek. I turned and wrapped my arms around her and gave her a deep kiss and as the kiss lingered on she flicked her tongue into my mouth and the kiss got even deeper. Boy was I ready to get started and so was she. We walked to the bedroom and as we walked I reached out and touched her ass. This time I wasn’t going to check myself, I was going to do everything I could think of to Emily. I opened her robe up and saw for the first time how amazing her breasts were. Her dark brown nipples were huge and so inviting. I put my mouth around her beautiful full breast. I’m guessing she has 36D’s and they are so firm and fun to play with. Emily undid my pants and reached in to grab my hard cock. As my drawers hit the floor Emily let out a gleeful yelp as she saw how big my cock is. Robert even chimed in and said, Honey, I think you have hit the jackpot. I don’t want to brag but I am blessed with a seven-inch cock that is super thick. My wife always says it is my girth that makes her happy. Emily seemed to share her exact thoughts.
Dropping to her knees Emily began to lick and rub my cock at the same time caressing my balls. I was in heaven, but I remembered it was all about Emily. I eased her onto the bed and gently spread her legs apart to reveal her gorgeous pussy. Her lips were thick and as dark as her nipples. Her clit was large and very suckable. As I spread her lips apart and began to insert my tongue into her I was amazed how brilliantly pink her vagina was. She was so wet I could taste her moisture immediately. Emily came almost right away. I had no desire to cum right away, I was going to make this evening last as long as I could.
I must have spent a half hour or more between her legs making her cum again and again. I began to work my way up from her clit kissing her beautiful little soul patch of pubic hair than on up to her firm tummy, still not believing she is someones, grandma, up to her amazing breasts and neck and finally her lips. While we were deeply kissing I slid my cock slowly into her and felt her heave and groan as I continued to push deeper inside her. She took all that I had and continued to moan as I pumped her long and hard. God, it is great to be with a woman who knows how to fuck. We went at it from every angle and I swear I felt like a teenager again. For the better part of an hour, we fucked until I finally asked her how she wanted me to cum? She said she wanted me to fill her pussy so I let go and it felt like the world was exploding.
After catching me breath I pulled out got off of Emily. Robert, who had been quietly standing by the whole time laid down between Emily’s legs and watched as my cum began to run out of Emily’s pussy. He was smiling with delight as his wife spread her lips wide for him to enjoy the sight.

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? Every encounter we have had since then has always been new and fresh with ideas and fantasies. I could bore you with the details for hours. Needless to say, the three of us have developed a deep and passionate friendship.

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, Thought it was an important experience to have, Making new friends

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? No one else knows.

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? I did it out of friendship and still believe my motives are good.

What was the WORST thing about this hookup? I wish I could share it with my wife.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Even though my wife is not part of this I do think our sex life has improved because I feel so blessed to have her, Emily and Robert in my life.

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

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

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? I am glad I agreed to meet with Robert and Emily. Sex is a very important part of who we are. When Robert lost his ability to make love to Emily it didn’t mean he lost his way to love her completely. In fact, I believe they are the best loving couple I have ever met.

What do you think about the Casual Sex Project? Very interesting to hear about how others enjoy sex.

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