Hot “Match” Up

by JWToyz

What’s your gender? Man
How old are you? 65
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation:
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Oversexed
How many sexual partners have you had in your life (including oral sex)? Too many to count (100+)
How many hookup stories have you here posted before? 1

Hot “Match” Up

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For less than a month

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? J is a very slim and sexy looking 50 year old that I met on Match.com. I was single (widowed) at the time and looking for a casual, and fun (non-exclusive) relationship. It’s hard finding women on Match who just want to have a good time. Most are looking for their “last best love and marriage”. J and I connected on Match and had a few very nice phone conversations. She lived about 150 miles away, so it took a while for us to actually make a date. Her pics were quite good. She was on the skinny side, but with large tits. We clicked quite nicely by phone. She had a sexy voice and laugh, and our phone chats became more sensual over time. It was obvious that she liked sex, BUT she was not looking for “just a hook up”. We finally agreed to meet. I was to drive to her city and book a hotel nearby.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I arrived at the hotel and asked to upgrade to a suite. My plan was to take her to dinner then invite her up to the suite for a nightcap. I thought that having a suite with a real living room would increase my odds of seducing her upstairs. The hotel offered me a great price on their presidential suite which happened to be open for the night. It was an apartment-sized suite with a living room, dining room, kitchen, AND a huge master bedroom. Perfect!

When J arrived, I told her that I had a great big suite with a nice view and a chilled bottle of champagne with some snacks. She was a little reluctant but decided to risk it and come to the suite. When she rang the doorbell and entered the room she declared, “wow!” She was obviously very impressed and now more comfortable. I showed her around and we took in the view from my balcony, then we sat on the large sofa for some champagne and conversation before going to the hotel restaurant for dinner.

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? J was wearing a short black dress which showed off her thin, fit legs. It was a low cut spaghetti strap dress that also showed offer her large and very perky boobs. I could tell they had been enhanced since they stood up so firmly. She was not wearing a bra, so her nipples were evident and asserting themselves through the silky fabric. She may not have intended to fuck on the first date, but she surely knew she was going to turn me on. She did! As we sat down on the couch, I already had an uncomfortable boner in need of rearranging (and some fresh air!). Some very flirty chat ensued as well as lots of touching and seductive laughing. At one point, I asked if I could kiss her. She said “what took you so long”. I leaned and expected a nice soft, sensual kiss that quickly turned to heated, heavy tongue fucking and hand groping. I caressed and squeezed her right breast and nipple. She arched her back and let her legs open. I took the bait and caressed her inner thighs.

She reached down and moved my hand up to her panties which were already soaking wet. I pushed her skimpy panties aside and began to stroke her cunt lips and clit. Moaning and grinding commenced! I inserted my middle finger applying pressure to her clit. Her pussy was so hot.. like an oven. I don’t think I’ve ever felt anything like it. A little finger fucking and her pussy began to spasm. “Oh God, I’m cumming!” Her hips and ass bucked and squirmed, fucking my hand and fingers. It’s been a long time since I jizzed in my pants, but with this crazy hot response, I was certainly close. J recovered while we continued to deep french kiss. She unbuckled my belt, unzipped my pants, and reached in to let my hard dick out for some air. I was leaking pre-cum. She dropped to her knees and pulled my slacks down with one pant leg on and one-off. She opened my legs and began devouring my cock and balls. There was lots of sloppy sucking and tongue action. She made incredible moaning noises like a someone enjoying a meal after starving for a few days. I felt my balls tightening. I was close but didn’t want to cum yet. (At my tender age, recovery time ain’t what it used to be). I pulled her back up and she straddled me. She grabbed my cock and literally slammed her pussy down on me, taking me all the way inside. I could feel the back of her vagina. We were both breathing heavy and moaning loudly. It was a good thing we had such a big suite or we surely would have disturbed the peace.

We fucked on the couch for like school kids, and before I lost control, I picked her up (she’s a lightweight spinner) and, with my cock still inside her, maneuvered to the bed. I laid her on her back, spread her legs wide and high, knees to shoulders, and buried my face into her hot, wet, well-fucked cunt! She loudly announced another orgasm and bucked against my face. Her pussy going into spasm again. I turned her over, pushed her legs together, and entered her from behind. I slammed her ass and she came again loudly and I lost it too. My dick spasmed for 20 – 30 seconds. I laid on top of her, spent. As my dick began to soften, we rolled over so she could lay on me. I could then feel our fuck juices drip from her pussy onto my balls and legs. What a HOT, HOT fuck! The rest of the night is a bit of blur. Room service was ordered, but I can’t remember what we ate other than that we did so naked. After eating, we turned on the tv, but I can’t recall what we watched. We started hot making out during the show and ended up fucking on the balcony with me fucking her from behind while she leaned over the railing with her tits out, moaning and watching hotel guests meandering around the pool and bistro 20 floors below. I kept hoping they would look up and watch the show. We eventually slept in our funky, spunky, sweaty mess. The scent of sex was heady. We woke up early and showered together, then fucked some more before we both had to leave.

So began a great FWB “friendship” that still happens from time to time. More stories to come! Stay tuned!

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? We have become great fuck buddies. She has a guy in her life now and I am engaged. We still talk and text from time to time. We fully intend to get together when our schedules permit for some seriously hot, casual fun. We look forward to visiting a swingers club sometime soon. She’s keen on having an extra cock (or three) and I can’t wait to fulfill that fantasy!

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)

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? Somewhat

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 a few close friends

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Crazy, hot sex with a true MILF that I thought was just going to be a first (sexless) date.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am a casual sex fan so this was not a problem for me and just fit with how I think things should be between two (or more) compatible, consenting adults.

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? My fiancé is quite sexually liberated, but also prone to jealousy, so I just don’t want her to get hurt. She and I are considering “swinging” a bit. That said, she’s more inclined to like it if I bring a new “cock” (especially a dark one) around. Not sure if she’s all that open to me enjoying strange pussy. Therefore, my time with J may not be all that viable.

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? Sex is like food! We all need both. Restricting our sexual diet makes no sense at all. If we are honest, open, and safe, we should be able to expand our sexual menu. I like the idea of exploring an expansive sexual cuisine with my fiancé lover. I think doing so has the potential for enhancing our love and relationship. After all, if kept in a playful spirit, it’s just dick and pussy! No big deal! Enjoy!

What do you think about the Casual Sex Project? I’m a fan! Glad to be able to contribute. I plan to share more!

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