The Hungry Cougar

by ty

What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 1

The Hungry Cougar

How long ago did this hookup happen? 2 days

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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? She is 42, about 5’6″, average weight, black haired, and blue eyed. She has nice tits, is a bit of a pot head, and very flirty. She feels a little past her prime, but still quite attractive in that milf/cougar kind of way. She told me that she has a couple kids and is engaged. She started working with my company six months to a year ago. She was friendly and flirty from day one. At first I just assumed that was her personality, but I started to notice she was only really flirty and close with me. A few weeks ago, at a company Christmas party, we got drunk and she asked for my number. I gave it to her, and she texted me immediately, asking if I had a nice cock. Things escalated quickly, and we went to her car where we fooled around. During which she gave me head and swallowed, she was also a squirter. She offered to drive me home so I didn’t have to catch a cab. When we got to my place, we continued to fool around, and with very little convincing we had a quickie. The following week at work, she told me she wanted me to fuck her again, but more than just a quickie, so we set it up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was Friday, we planned to meet at my place after work. All I could think about that day was banging her again, she was a bit of a nymphomaniac and had a lot of pent up sexual energy. It didn’t sound like she was getting enough from her fiance. Around lunch time she sent a text asking if I would cum on her face, I’d never had a woman actually ask for that before. The end of the day arrived and I went home and took a quick shower, she arrived shortly after and attacked me the second I opened the door.

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 made out very briefly before she instructed me to take off my pants. Then she began stroking my cock, admiring it and telling me how big it was, saying it was the biggest she’d had in probably 15 years. She began sucking it, she knew what she was doing, I’ve had a few women that were really good at sucking cock, but she was like porn level good. She’d try her best to take it all but couldn’t get much more than six inches, I hadn’t jerked off all week so it didn’t take long before she had me on the edge. I asked where she wanted it and she looked up at me and said “cum on my fuckin face”. She leaned back at the last second as I gave my cock a few good strokes and erupted. The first burst hit her cheek and she tightly closed her eyes but stuck out her tongue, another half dozen ropes of cum splattered from her chin to her forehead and dripped to her tits. I sat down on the edge of the bed as she opened her eyes and looked up at me, a little shocked with how much cum there was, she looked at her self in the mirror and licked it off her finger as she told me she’d never had a guy cum that much from one orgasm. I handed her a towel to clean up, and she asked how long I needed before I was good to go. I grabbed her hand and put it on my semi hard cock and told her to find out. I was hard again in a few strokes and grabbed a condom, she hopped on and started to ride me, she had her first squirting orgasm in under five minutes, then another, and another, and it just kept going. Every time I’d get close, she’d squirt and I’d have to build up again. She told me she wanted me to cum so I pulled her to the edge of the bed and took her doggy. I fucked her ruthlessly, bottoming her out, she blurted out between yelps that I was hitting her cervix. I eased up, but she yelled for me to keep going, she would go to pull away to squirt but I wouldn’t let her, I was close and determined to finish. Grabbing her hips, I pounded everything I had into her until i came, we both collapsed to the bed my cock still throbbing inside her. I finally got up and pulled out tossing the condom in the trash, she laid there catching her breath as I laid beside her stroking my cock. She rolled onto her back and took one look at my cock and said, “Are you seriously fucking hard again?” I laughed and shrugged my shoulders and she says “I’m not complaining, I mean most guys can barely manage two rounds in a night, but shit I’m not sure how much more of a pounding my pussy can handle.” I asked if she wanted to stop and she hesitated then said “one more time” she tried getting me to go bareback but I insisted on a rubber, we went for a good 45 minutes, my sheets were completely soaked. I could tell she was loving every inch but she was getting exhausted, I flipped her onto her back and pulled her legs to my shoulders and folded her in half, for the first time she actually looked concerned and blurted out “No, No, Oh fuck you’re WAY too big for this position,” but I just eased my cock in, her eyes rolled back and she began mumbling gibberish. I was hitting deep, and she was begging me not to stop, I lasted all of five minutes as she clenched her pussy. We laid there for a bit collecting ourselves.

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 discussed possibly being fuck buddies, we will see how it goes.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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

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

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