[MF] Anonymous, Risky Sex With a Curvy MILF

Before my wife and I found each other and [started having our own adventures](https://www.reddit.com/r/Swingersgw/comments/fezm9x/a_few_more_outtakes_from_her_gangbang_last_summer/), when I was in my late 20s and early 30s, I spent a few years exploring the swinger scene as a single guy. This was in the heyday of Craigslist personals, and I had some great luck finding folks to play with. One of the biggest turn-ons for me was the anonymity of it all. There was nothing quite like meeting someone for the explicit purpose of sex, knowing that within a few minutes the clothes would all be off and you’d be deep inside this person that you’d literally just met. It focuses the mind on the urgency of fucking…no thoughts about relationships, consequences, personality…all that mattered was the act.

Most of my hookups during this period were with hotwife/cuckold couples that were looking for a guy to come in, act the role they wanted, and hit the road, which suited what I was looking for perfectly. I did have a few experiences with single women, however, and one really still stands out to this day. She was a short, curvy MILF named Tina, in her early 40s, divorced, with a teenage son who she shared custody of (so she often had her house to herself). I met her on a swinger personals site (as opposed to my usual haunt of Craigslist). Her profile pictures were some boudoir shots and they were absolutely stunning…she had red hair, huge (but firm) breasts, and a big curvy ass that I just needed to see her throwing back on my cock.

She messaged me first, and was very explicit about what she was looking for – a dominant guy in the bedroom for no strings fun. My profile on the personals site was targeted towards couples looking for dominant guys, and I guess that checked the boxes for her. Anyone who’s spent time as a single guy in the swinger world knows how incredibly rare it is to have a woman message you first on one of those sites…I was absolutely enchanted. I took the invitation to be aggressive and replied that I’d be happy to give her what she needed, but if she wanted me to fuck her right, I would need her to prove to me how badly she wanted it. I messaged her, “I want to walk into your house and see you on all fours, naked, dripping wet, ready to be fucked hard….”

Tina didn’t respond right away, and I was afraid I had overplayed my hand. As the hours wore on without a reply, I moved on mentally and chalked it up to “win some, lose some” (as you have to to stay sane as a single guy in that world…it’s not for the faint of heart, and rejection, changed minds, and last minute cancellations are pretty par for the course). Then my e-mail dinged (we hadn’t even exchanged numbers yet). “That sounds so hot! I want to meet you in public first though. I’m fixed, so you don’t have to worry about condoms.”

Pro-tip, guys – you should always wear condoms. But as we all know…it’s so much better without, and so much hotter to take that risk. We quickly agreed on a location to meet up that was close to her house, and we set a time. I got there first and again had nerves that she was going to stand me up, but she texted me and told me she was running slightly late. A few minutes later, she pulled into the parking lot next to me. We didn’t talk, or even get out of our cars – she just wanted to verify that I was who I said I was. After a quick thumbs up to each other to verify that it was on, she pulled out of the parking lot and I followed her back to her house.

As I pulled in to her driveway, I received a text. “Give me 5 before you come in, I’ll be ready for you. Bedroom down the hall, first door on left”

I waited in the car, idly wondering if this was a good idea – I literally had not yet talked with this woman in person, and our first contact online was the day before. She could be lying to me about having her tubes tied, she could be crazy, this could be some kind of scam…but I knew that I wouldn’t back out now, though. A picture of her on all fours, ass up, was already burned into my brain…I needed to see it in person.

After five minutes or so had passed I got out of the car and walked up to her door. It was unlocked, and I let myself in. As I walked back the hall I felt my erection pressing against my pants, my heart pounding a mile a minute, barely able to understand that this was really happening. I was locked in, thinking of nothing else than filling her up with the huge load of cum that was building in my balls. As I walked into the room, I saw her, exactly as I’d pictured in my head. She was fully nude, her knees on the edge of the bed, arched to expose her ass and cleanly shaved pussy, and she had her head resting on her arms, her curly red hair spread out in an arc across her shoulders and back.

She didn’t look back at me as I unzipped my pants and dropped them to the ground, letting my pre-cum covered, diamond hard cock spring free. I walked up behind her and grabbed her ass cheeks, spreading her wide open from behind so I could see how wet she was. Grool strung between her thick, long pussy lips as they pulled apart, and I knew that she wanted this just as much as I did. I let my cock slide from just below her taint, across the opening of her cunt, then down between her lips, mixing my precum with her wetness, and then teased her swollen clit with my cock head, with her slick lips draped on either side. She let out a low moan at this, the first time I’d heard her voice.

“You’re such a good girl Tina…such a good slut. Did exactly what I told you. Do you want to feel this cock in you? Do you want me to fill your cunt with cum?”

She moaned in affirmation.

“Not yet…I’m going to tease you until you can’t take it anymore…I want you to beg for it.”

I pressed myself in close behind her, pushing my cock tight against her clit, but not allowing her leverage to slide it inside. I reached around and started teasing her nipple, pinching it, while grinding the tip of my cock again and again against her clit.

“Please…ohhh….fuck. Please….”

I pinched her nipple hard, and she moaned again

“I can’t hear you”

“Pleaaaaaaase fuuuuuuuck meeeeee….ohhh….I need you cock….fill me up….”

I pulled back….grabbed her ass cheeks again and spread her wide. I slid my cock up now, the tip right at her entrance…and I slowly, slowly pushed myself inside the warm, wet depths of this woman who I’d met less than thirty minutes before, who was creaming on my cock and begging me to fill her with cum. I finally bottomed out, deep inside her, and I smacked her ass, hard. She pressed back harder against me, growling, needing me to take her.

I grabbed her hair and pulled her up, onto her elbows. I started to slowly thrust into her, pulling her back with her hair, taking care not to pull too hard but enough to make her feel controlled, to make her know that I was fucking her how *I* wanted to fuck her. I smacked her ass again with the other hand, picking up the pace, telling her what a good little slut she was, and how much cum I had for her cunt, spanking her again and again as I felt her getting wetter and wetter. The room smelled of sweat and sex, our bodies overheated, tense like piano wire, so much tension built up that our orgasms were necessary things now, or we would break.

I knew that she was close, and I wanted her over the edge. I pulled her hair back a little harder and told her I wouldn’t fill her up until she came on my cock, and she reached down and started rubbing her clit as I pounded her, faster and faster, until I felt her gush all over me, her pussy squeezing my cock as she started to cum. I couldn’t have held myself back even if I wanted to. I felt the first spurt of cum rise up from my balls and through my cock, shooting deep inside her. I pulsed again and again, draining myself into her, as she pressed back hard against me, trying to take it all.

Finally spent, almost collapsed on top of her, I raised myself up and grabbed her ass cheeks, spreading them again, wanting to watch as I pulled out. My cock was covered in our mixed fluids, and when the tip pulled out between her swollen, pink lips, a big glob of cum ran out out of her pussy and down over her clit, dripping onto the sheets.

I moved up onto the bed next to her, finally closely seeing her face and beautiful blue eyes, and we kissed for the first time, covered in sweat and cum.

Source: reddit.com/r/gonewildstories/comments/ifux1r/mf_anonymous_risky_sex_with_a_curvy_milf