My (39F) new old friend (44M), now with benefits [MF]

It has been a long time since I’ve posted here on Reddit. In the past, I shared stories about my out of control libido and my struggle with lack of interpersonal connection during the pandemic. It has been a frustrating time- getting my hopes up when I meet someone, only to be disappointed and feeling stupid for getting excited in the first place.

Near the start of this year, an old friend (I’ll call him A, 44M) and I started spending more time together. We have known each other for about 20 years, somewhat peripherally, but always had good feelings towards one another. He had previously expressed interest in being more than friends, but I was hesitant. I didn’t see him that way and was afraid to start hooking up and possibly lead him on or hurt him. When we started taking the occasional masked walk together, our conversations grew deeper very quickly. We both have crazy high sex drives, and were both struggling without having safe places to explore that energy. Relating to people is hard, and trying to meet new partners and develop some intimacy during the pandemic was nearly impossible. It was nice to be able to confide in and support one another in such hard times.

I had no prospects on my horizon, but women were crawling out of the woodwork to reach A. Several lovers from his past contacted him over the last few months, begging to play with him again, reveling in memories of their time together, all very centered on how great he was in bed. I didn’t know what to make of it. What had he done to these women?! We talked about it a lot and I wondered if I’d ever had truly fantastic sex in my entire life. I’d never thought of a former lover in the way these exes thought of him- as being something of a sexual dynamo, someone I would crave and ache for.

Once we were both vaccinated and it became safe to start dating, we had more to talk about on our walks together. I started meeting up for dates in person with other vaccinated people, finally enjoying the potential for intimate physical contact. After one utterly disappointing hookup (Don’t leave your girl hanging without an orgasm just cause you busted your nut already, dudes!), I found myself flustered with sexual energy and no outlet for release. On top of that, I had had some stressful days at work, felt full of tension, and wasn’t even feeling satisfied from self pleasure. I reached out to A.

A was well versed in polyamory and casual sex- and had a much greater understanding of these kinds of dynamics than I did. Did he think it was possible for us to begin a sexual relationship that was aromantic? Did he think we could keep sex separate from emotions? I thought even making out with him might feel weird, since we were such old friends- but then I thought what’s the worst that could happen? Why would I consider sharing my body with men from apps who aren’t concerned with female pleasure, when my dear friend is right here, eager to please me? I don’t trust men easily, so letting someone into that space isn’t something I do readily. But here, I wouldn’t have to worry. My friend A understood boundaries and consent, sexual health, and clear communication. He loved me like a friend, and I loved him. And I needed to understand what it was that his former lovers were so obsessed with- some even 10+ years after the fact.

He came over. We sat on the couch. I was stoned, slightly hesitant, and giggly. He turned to me, took my hand, and leaned in for a kiss. His lips were soft and tender at first. We kissed slowly. I soon felt my breathing change as I took in the sensuality of the moment and truly started to kiss him back. Both of us hungry for passion and sexual satisfaction, suddenly our kissing took on a greater sense of urgency. My hands pulled at his hair while I kissed him deeply, exploring his tongue with mine. He wrapped his arms around me and pulled me closer to him. When he did, I straddled one of his legs and rubbed myself against his knee while we continued to make out. He felt me grinding against him and was thrilled to know that he was getting me excited. He took my hand and placed it on his jeans. I gasped when I felt his cock- so hard, long, and girthy. Honestly, I hadn’t planned on doing much more than making out with him. I thought we would take things slow, making no assumptions about what this connection might mean or how close we might get. I even thought I might keep my pants on. But here I was, feeling him in my hand through his pants, my wetness gathering between my legs, and all hesitation just faded away. Everything felt so good and I needed more. Suddenly, I was open to anything and everything.

He must have sensed that I was thinking things through while we were fooling around. He asked if it was ok to take off my pants and I said yes. I was wearing thin black leggings with a short black skirt over them, and a local band’s t-shirt. He pulled off my skirt, leggings, and thong all at the same time. He was now sitting on the floor in front of me, and I was still on the couch, only in my t-shirt with a bra underneath. He reached out with his hand and felt my shaved pussy lips for the first time, lightly pressing against them until they opened slightly and he could feel the slickness inside. He moaned when he felt how excited I was, and I caught my breath in my chest as he began working his finger up and down my slit, teasing the area around my clit, but not actually touching it. He was getting me worked up and he knew it. While making eye contact with me, he slid his finger inside of me. I closed my eyes and tilted my head back as he slowly slid his finger in and out of my wet pussy. He asked if he could kiss my kitty and I said Hell Yes! Suddenly his head was between my legs, tongue playing with my hardening clit while his fingers continued to work their magic inside of me. I started bucking my hips against his mouth and nose. He grabbed at my thighs, trying to stop me from squeezing his head too much as my entire body responded to his tongue and touch. I had my hands in his hair as I fucked his face, telling him how much I was enjoying his mouth on me, telling him I wanted him to make me come. I whispered his name as my body started to tremble with my first orgasm. He licked and sucked and kissed me until I came to rest and catch my breath. Then, he stood up, reached out his hand, and said “May I escort you to the bedroom, mi amiga?”

That was two weeks ago now. And we have fucked each other multiple times on 12 out of the last 14 days. I promise I’ll write more at another time. There’s plenty to tell.

Source: reddit.com/r/gonewildstories/comments/n9gey8/my_39f_new_old_friend_44m_now_with_benefits_mf