My Totally Unintended Encounter with a Long Time Friend

This post is sponsored by Trust Massage Oil.


What’s your gender? Woman
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? Dallas
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Physician
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1

My totally Unintended Encounter with a Long time Friend

How long ago did this hookup happen? 4 months ago

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

How would you best classify this hookup? One-night stand

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? Billy was a cute guy, he was about 6′ tall and roughly 240 pounds. I had known Billy almost all my life. Growing up he was my brothers best friend and was at our house more than his own. He ate dinner with us almost every evening and I basically thought of him like one of my brothers. As a kid he teased me unmercifully but always stood up for me. We remained friends after I left home and I saw him at every family event when I went back home to Michigan.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was no planning, Billy was 57 years old and had been out of work for almost two years. He came to Dallas for a job interview with a marketing promotion company who was opening an office in our hometown back in Michigan. My mom had told me he was coming and I called him. He was covering his own expenses and would be in town for four days and I offered him to stay with me since my husband was out of the country traveling with his job and we had plenty of room.

Billy and I had a very weird relationship, we could pick at each other or be like best friends. I never thought of Billy in any sexual way at all. He was always my big brother figure. I had got home from my hospital rounds late and walked into the house around 9:30 that night. I went into the bedroom and put on a men’s extra large t-shirt and came back out to the kitchen. I liked wearing the men’s shirts around the house adn they came almost to my knees covering my 5’4″ 115 pound frame fully. I got a snack and walked into the family room and Billy was lying on the couch in a pair of basketball shorts. I told him to scoot over and sat putting my plate on the end table and asked him how his day had gone.

Billy was very talkative and I finished my food and drink and told him I needed to brush my teeth and start to get ready for bed. I told Billy he could follow me if he wanted to continue talking. Billy talked the entire time I was getting ready and then followed me into the bedroom and sat on the end of the bed next to me after I lay down.

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? Billy started to get up to leave and then leaned over and kissed me. We had always exchanged light kisses on the cheek but this time Billy kissed me squarely on the lips and instead of it being a small peck it lasted a moment or two. As his face moved a few inches from my face Billy looked into my eyes and said “Thank you for being so wonderful and supportive. I really needed to talk tonight and I know your busy. Thank you.” I told him I enjoyed our conversation and then asked if he wanted to lay down and talk until I was ready to fall asleep. It still did not seem wierd as we had lay in a bed or on a couch many times over the years.

I was lying on my back and Billy lay on his side facing me. I noticed our bodies had moved closer together as we talked and Billy had placed his hand on my stomach over my shirt as we talked. I felt Billy’s hand move under the hem of the shirt and up my stomach until he had cupped my left boob. I felt shivers of excitement run through my body and my nipples became erect. It was the first time Billy or I had made any sexual move or touched. As we continued talking Billy moved his face closer and we began to make out. I reached down and ran my hand over Billy’s shorts feeling his cock that was semi erect. I had never seen him naked at least that I could remember but he seemed to have a nice, thick cock.

Billy pulled my shirt off me over my head and then while we kissed he pulled my panties down off my hips and began to finger my pussy which was very turned on and wet. Billy had no trouble getting his finger up inside me and it felt amazing. Billy pulled me over onto my stomach and began to lick my pussy from behind and alternating licking my ass which was a weakness for me and pushed me into an orgasm that echoed throughout our house. Once I was recovered I told Billy to stop and I pulled his basketball shorts off and took his cock into my hand. He as between 7-8″ hard and probably 6″ around. I got onto my hands and knees and took him into my mouth trying to take as much of his length as I could. Billy was moaning and obviously enjoying himself and I continued until I felt him begin to tense his body and I felt his cock begin to twitch before he exploded a load of cum into my mouth. I did not release his cock until he was completely drained and half limp.

We lay side by side snuggled up together and I felt Billy’s cock get hard again as he had it between my ass cheeks laying against me and holding me. I moved my hips around and he was at the entrance of my pussy as I reached down and guided his cock inside me. Billy pumped into me from the side and then after a few minutes flipped me onto my stomach and was driving into me from behind. I was on the verge of climax and we changed up position again with Billy ontop of me and kissing me as he fucked me hard and fast. It did not take long before we both erupted in orgasm and Billy filled my pussy with his hot load.

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? Billy was still sleeping when I got up and had to get ready for work. I left the house with him still naked in our bed. When I got home that evening Billy acted a little differently and I got something to eat and sat on the couch next to him. I casually mentioned “I can’t beleive that happened last night. I really enjoyed it though and I hope it will not change our relationship.” Billy waited a moment and then told me he had worried about it all day and wanted to call me to apologize. I told him he had nothing to be sorry for and we were both adults and it was totally consensual. That conversation seemed to remove the tension in the room.

Billy had got the job and would be in town for a two week training program starting next month. I told him he could stay and he thanked me.

When Billy returned he and I could not keep our hands off of each other and fucked every night he stayed. I begged him to fuck me in the ass one night and that was probably the hottest night we had together.

I have not seen Billy since this happened and did not get home for the holidays where he was at my parents house. We have talked very briefly but nothing serious. I still see Billy and feel like he is my big brother but when we were together I just felt very comfortable and at ease with him.

I am actually looking very forward to seeing him again next time and hope that we can generate the heat and passion we shared on his trip.

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

What were your motives for this hookup? 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? I don’t know / I’m not sure

Did you consent to this hookup at the time? I did not vocalize anything, It happened and I did not try to stop it.

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? There was never any vocalization but we both went with what was happening in the moment.

To whom did you talk about the hookup? How did they react? I talked to my husband. He was mildly upset but we have always separated sex and love and agreed that if anything ever transpired that the other was able to have a sexual fling in the moment. His biggest area of concern was in that how close Billy and I are and he cautioned me to not allow it to go into a love relationship. I told my husband I would like to have a threesome with him and Billy but we left it saying we can discuss that further when and if the situation ever presents itself.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? The total lack of planning and spontaneity of the situation. It was pure raw passion.

What was the WORST thing about this hookup? My fear that it will inevitably alter the brother – sister relationship we have had all our lives or that my family may find out what happened.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really

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? I am glad we both were able to go with what happened in the moment and that it did not effect our relationship or bond.

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 think that causual sex among mature adults is something that could greatly benefit peoples lives, self image, relationships and even their health. People are far to uptight about sex in our society. My husband adn I have both had a couple casual sex partners during our 30 years of marriage and it has been positive for us overall.

What do you think about the Casual Sex Project? Just came across it but enjoy the stories so far.

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