My First Experience

by Cathy

What’s your gender? Woman
How old are you? 57
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
Highest education received: High school diploma
What’s your occupation? Housewife
What’s your current relationship status? Engaged/Married (open)
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)? 6
How many hookup stories have you here posted before? 0

My First Experience

How long ago did this hookup happen? 2 month 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? Just met that day

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? Terry is an attractive, rugged, muscular, light-complexioned African-American. Tall, I guess he was about 6 feet since I only came to the top of his chest. He was in his late forties, with a touch of grey in his hair and goatee that made him look so distinguished. A good talker and a good listener.
I met him at the motel my husband and I stopped at on our way home from our daughter’s, we had just spent Thanksgiving with them. The weather was horrible and we were in a hurry to get home so we looked for a motel that had an indoor pool and dining area so we could try and relax.
Terry arrived at the pool and sat down by us. My husband and he hit it off right away. At first, it was just about the roads and the weather but soon discovered that they had a lot more in common including business. Hubby decided that he wanted to sit in the Jacuzzi and then the sauna, but I didn’t care for either of them and hopped back in the pool to swim. Terry joined me. I guess we flirted a bit; he thought that I was younger than him and commented how good I looked in a bikini. It felt good to be flattered, I enjoyed the attention.
When my husband came out of the sauna, he asked if I was finished and that he was going back to our room for a nap and watch TV. I told him that I’d join him soon but wanted to swim for a bit more. I did swim some but spent the next hour just talking with Terry about trivial stuff. I found it comfortable to be with him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Honestly, the actual act of the hookup might have been that night but it really all started a year before this. My husband had prostate surgery six years before and has trouble maintaining an erection. Oh, we’ve had a sort of sexual life, but due to his frustration lately, he is less interested. About a year ago, he mentioned that I was still an active, good-looking woman and that he loved me so much he thought that I should think about finding someone else to meet my physical needs. I was confused because at first I thought that he was suggesting divorce and I thought our marriage was more than just sex. He reaffirmed that he loved me, that he wasn’t considering divorce and then he was blunt and said I should get a FWB. I told him the truth. It would be great to have sex again, but my reservations were about whether he would be able to handle it without getting jealous and how it would affect us. Also, in the back of my mind, I was unsure if he was just testing me.
When I got back to the room, hubby was lying in bed watching the weather, I slipped out of my suit and plopped into bed next to him. I told him that I had a good time and if he was ready, after I showered we could get dressed and get something to eat. He remarked that I was really excited by that guy and was very flirty. I laughed at that but then he asked if that was the type of guy that I’d like to have sex with. I said that he was being silly, but told him that yes I wouldn’t mind having sex with him, but I doubted that he’d want an old woman like me.
What a coincidence, while we were waiting for our table, Terry showed up. My husband immediately walked up to him and invited him to dine with us. No one likes to dine alone is what hubby said to him. We had a great meal and drinks, it was so much fun. Terry excused himself to go to the bathroom and hubby leaned over to me and said, “Here’s your chance. I’m going back to the room, you can tell him that I was tired or not feeling well,” and he got up and left.
My head was spinning, Terry came back and sat down, the first thing he asked was where my husband was. I was running excuses in my mind and finally said that my husband has prostate problems and didn’t feel well and was hoping that Terry would keep me company until we finished our meal. He gave me his sympathy and said that he would be honored. Even so, we finished our meal in an eerie silence. We talked a little while we were waiting for the check only to discover that hubby had taken care of it. Terry leaned over to me and asked if he could ask me something personal. He wanted to know if we were some sort of swingers that looked for black men. I know I blushed, I felt the warmth in my face. I assured him that we weren’t, just an old married couple adjusting to our problems. I thought that would be the end of our evening but then Terry said he was relieved and if he could buy me a drink as an apology.
We sat at table in the bar and sort of made a joke of that conversation. I wasn’t by any means drunk, I pride myself on being able to hold my liqueur, but I do get honest and after one more, I told him truthfully, about my sex life, my husband’s problems and what he told me to do about it, and that I found Terry extremely attractive and would be the kind of guy that I’d like to meet. It felt so good to get it all off my chest and he listened so intently and had the most sincere look. When he finally spoke, the only things he said were, “You really find me that attractive?” and “Are you really sure you want this?” I said yes, and he took me by the hand and led me back to his room.

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?  We did a lot of kissing once we were in his room. He asked me a couple of times if I was sure I wanted this. All I can say is that all of my inhabitations were gone. My brain was swirling around, I was as giddy as a teenager. The excitement of his hands exploring my body, the soft passionate kisses. Everything he did excited me, he was so deliberate, from slowly undressing me, gently fondling and kissing my breasts to slipping off my panties and feasting on me.
I had an orgasm and was trying to pull him up so he could mount me but he continued to give me oral and asked me what I wanted. I told him I wanted him inside me. I helped him get undressed, his penis was more than adequate and it was so good to just lay next to him and feel his erection against my belly.
We started out in missionary, then doggy and finished with me on top. I orgasmed in every position. He finished inside me. We cuddled and snuggled and kissed. We talked about how good the sex was. He apologized for cumming inside me without asking.
We both got our second wind and went at it again. It was even better as he encouraged me to be vocal, I actually asked him to do me harder and I had this long orgasm that was punctuated by his final thrusts.
We slept for a bit, I got up, took a quick shower, gathered up my things and dressed. As I left, I  gave him a last kiss, thanked him, and went back to my room.

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 slipped into bed with my husband. He put his arms around me and I fell fast asleep. I was totally exhausted and drained. I woke up, it was late, almost checkout time. Hubby had my coffee ready and told me I needed to hurry. The only time he has mentioned it, he asked if I had a good time.

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, Intoxication, To feel better about myself, To feel more desirable

How intoxicated were you? A little tipsy/high

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Just my husband.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I got rid of years of sexual frustration that I didn’t realize I had.

What was the WORST thing about this hookup? I don’t know

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, it definitely has, I just haven’t been able to get it all straight yet.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? Maybe that I’d have been more open to the idea when my husband first suggested this.

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? On my part, I think that because it was casual, it lent a certain excitement…

What do you think about the Casual Sex Project? I like it

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