My first simultaneous orgasm, and the first time I tried anal [MF]

Five years ago, I was in the unfortunate situation of having broken up with my girlfriend, but still living out the lease together. Yikes, I know. So I did my best to get out of the house as often as I could. One prong of this approach was to post and respond on the r4r subreddits: /r/dirtyr4r, /r/BaltimoreAndDCr4r, even /r/Troll4Troll. Yes, there is such a subreddit, which I only found through using the somehow then-working search function and looking for “f4m” and “VA” or “DC”. It was there that I found the (long since deleted) post that described a 27 year old woman who was traveling for work and would be in town for a week and was looking for a date. I messaged her and described myself, a 25 year old 5’10 athletic guy with brown hair and a beard, a lot of chest hair, and some tattoos. I included a picture and listed a few interests, but didn’t get my hopes up– internet personals aren’t known for their high response rate.

I was surprised when she replied with not only a cheery message, but also a couple lovely pictures. Lavender was around 5’9 and was blessed with flawless pale skin and amazing curves, a fit waist, big brown eyes, and dyed hair. One picture had it silvery-white, and another, more current one, had it as a teal bob . I was definitely a fan. Our conversation flowed easily and we eventually moved to kik, where we planned a date at Potbelly’s in a few days. We kept talking, and she straight up asked if sex is on the table, assuming we enjoy each other’s company. I replied with a resounding Yes, and the flirting got heavier and heavier. She eventually said something like, “Do you have a favorite color? Just curious ;)” And immediately, my perverted mind assumes she’s asking what color panties she should wear. Since I’m a sucker for seeing wetness, I tell her something along the lines of light orange or mint green. I don’t pry and I don’t tell her my presumptions, I just keep my excitement to myself.

The day of, the flirting had turned to sexting, and I was killing it. She told me how wet she was, how hard it was to focus on her work… I had to keep myself from jerking my dick sore before I even met her. When we did meet up, I had on a pair of brown jeans and a black v-neck, but she looked incredible. Skin tight jeans that showed off her ass and her slender waist, and just a plain (but form-fitting) grey top. With the shoes (pumps? platforms? I don’t remember) she was an inch taller than me, but neither of us cared. We got our sammies and sat down to eat. This being five years ago, I can’t even tell you what we talked about. I do remember, however, the way our legs kept getting closer under the table, until they were touching. I also remember how I pushed the contact further by placing my hand on her knee. After about an hour or so, I asked if she’d like to leave. We left, with her heading out the door first and me marveling at her ass some more. We walked out together towards our cars and somewhat abruptly, I said, “I can’t wait til we get to the car,” and grabbed her by the hips into a kiss. I pushed her into the wall of the Potbelly’s (protecting the back of her head with my hand) as we continued making our fervently, and my free hand squeezed her ass. When we pulled back, both breathless, she looked at me with such hunger that I felt like I’d burst out of my pants. “You’re coming back to my hotel,” she said. It was a statement, not a question. Not even an offer. A command.

We met again in the lobby and hurried towards the elevator, where we continued our kissing until the ding, and the doors opened to a few people who must have seen our red faces. We got inside and tore our jackets off, pawing at each other and panting every moment our mouths weren’t connected. I kissed her neck and bit her, pulling her hair down behind her back to give me more access. Her shirt came off, then mine. I kissed her stomach and squeezed her breasts and grinded my bulge between her legs as I undid her bra. Her pink nipples were diamonds in my mouth and she moaned as I sucked on them and used my teeth. When I kissed my way back up to her mouth, she said, “I want to fuck you so badly,” but I responded, “Not before I make you cum.” She practically purred as I made my way back down her body again and peeled her jeans off. To my delight, my assumption was correct– she was wearing light orange panties, and they were soaked. I spread her legs and pressed my face into them, inhaling her wonderful scent and kissing her through the gusset, and I remember she wasn’t prepared for such a lewd display, and she gasped and moaned much louder. My cock was straining my pants and I was so turned on I had to be careful about grinding too much into the bed lest I cum from just that.

I kissed her inner thighs and groaned at how good her pussy smelled and how wet she was. When I pulled her panties off I made a show of pressing them to my face and inhaling her scent, and she later told me it was one of the hottest things she had ever seen. What one of the hottest things *I* had ever seen, though, was her freshly shaven pussy, bright pink and dripping with arousal. I wanted to tease her more, I truly did, but I couldn’t help myself. I buried my face in her folds and licked every inch of her I possibly could. Her lips, deep inside of her, the hood of her clit. Each flick of my tongue against her little bead made her jump and curse and blaspheme loudly. Before I could even get my fingers involved, I heard her say, “Fuck fuck fuck I’m gonna cum,” to which I kept doing exactly what I had been, which was licking her clit from the underside as my lips kept it in place. She bucked her hips and I held her steady as she howled through her climax, finally gripping me by my hair and pulling me up to her again. She kissed me with an even more intense hunger than before, licking her juices from my chin and undoing my jeans.

Once she fished my cock out, she looked at it with these hungry eyes and complimented its size. After stroking my ego, she began stroking the shaft, and then devoured it. It was the first time I had been deep throated and it blew my mind. “Wait no,” I protested after a few minutes of sloppy, intense work, “you’re gonna make me cum.” Nothing. “Please, Lavender.” I didn’t want to bust just yet, I needed to fuck her. I grabbed her by her hair and pulled her away mustering a fierceness I didn’t feel. “You’re going to lay back and spread your legs and I’m going to fuck you until you cum on my dick.” Her subby tendencies took over and she did exactly as I told her while I put on a condom. I batted my cock against her swollen pussy lips, each impact eliciting a gasp and a shiver. She pleaded with her eyes, biting her lip and using her legs to pull me into her. The tip slid in first and we both breathed a sigh of relief. She was warm and wet and tight and just perfect. Her legs worked harder to draw me further in, and I was in no place to resist. I sunk in to the hilt and my elbows damn near collapsed it felt so good. I heard her mumbling something, but it was so quiet at first, I thought she was just having trouble breathing. When it got louder, I recognized the slurry of noises as, “… fuck me, fuck me, fuck me.” It kept getting louder until I reared my hips back and drove into her. She stopped begging, dug her fingers into my shoulders, and pulled me in for a kiss. I still tasted her juices on her tongue and I began fucking her as if my life depended on it. She released me and began gripping the sheets as I looked into her eyes with what must have been a lust that hadn’t been properly sated in at least a year. I was vicious with her, and she ate up every bit of it. I couldn’t even keep kissing her because I needed to breathe, but her breasts were shaking and her radiant face was contorted in ecstasy, and I knew I wouldn’t be able to last too long. Fortunately, she announced that she was about to cum and please don’t stop. I told her I was going to cum too and she gripped both sides of my head and looked like she was about to cry when she finally told me that she was cumming. I dropped to my elbows to kiss her raggedly as I kept pumping into her. I filled the condom and with each throb she quivered and moaned into my mouth again. I kept on thrusting until her legs locked around my ass and held me there, our aftershocks echoing with one another.

After a period of catching our breaths and saying “Oh my god”, she told me that was the first time she had ever had a simultaneous orgasm with someone, and it was mine as well. I finally pulled out and we cuddled for a while. I found out that her query about my favorite color was indeed meant to suss out what panties I’d like, she showed me the dildo she’d been using all week, and she asked if I’d ever done anal. I told her no, that I’d been very interested in it, but had gotten no further than using a finger or my mouth. When she told me she loved it, I had her turn over flat on her stomach and began massaging her ass. Much of the arousal of her pussy had dripped down to her asshole, so I used it to tease a finger there. I alternated between that and my mouth, and I was already hard again. She felt it on her leg and told me to get a condom and the lube. I watched as she fingered her ass with a healthy amount, and I lathered some on my rubbered cock. Going slow was a given, so I eased myself in, pausing every little bit to make sure she was ok. I ended up on my elbows, kissing her neck and her ear as I sunk in deeper. She began rubbing her clit and moaning her assent every time I made sure she was still enjoying it. “You can go harder,” she whispered, and so I did. Not too hard, not nearly as hard as the first time, but I began rocking back and forth. It was slower and far more sensual, and she kept moaning my name and telling me how good my dick felt. She came once, and I felt it in her tightly puckered asshole. She started begging me for my cum, urging me to cum in her ass and fill it for her. She started grinding her ass back into me, and I buried my head in the crook of her shoulder as I started cumming. She could feel each pulse, as groaned as she milked me of every last drop.

“Wow,” I breathed. “Did you enjoy your first time?” she asked, and I could only laugh. We spooned for a while until it was getting late. She told me she usually showers at night rather than in the morning, so I offered to join her before I leave. We washed each other and made out and washed each other some more until I got hard again. She dropped to her knees and didn’t let me resist this time. She deep throated me with no problem, the glug glug glugging sounds getting lost under the patter of the falling water. Her hands were on my ass and kept looking up at me with those big, pretty eyes, and I could only marvel at her lust. She pulled away at one point, shuddering, and I thought she was crying. I asked if she was ok, but she told me that she came again. I was astounded and ridiculously turned on, and it only took another twenty seconds or so of her oral skills before my knees buckled and I came in her mouth.

We dried off and I asked if she was serious, if she had really cum without even touching herself. “It was so hot,” she said, “and the water was dripping down, so that helped.” That she had a hands-free orgasm while giving me a blowjob is still something I masturbate to to this day.

I saw her a few times before I left, and we had a few more great experiences. We eventually tried a long distance thing (~6 hr drive) but it was too much. We still have those lovely memories, though.

Source: reddit.com/r/gonewildstories/comments/jaib8l/my_first_simultaneous_orgasm_and_the_first_time_i