This will be kind of long, but worth it, I think. I’ll still try to keep it sexy W
hen I was 29 and in grad school, I was starting to act like a big manwhore. At one point in the spring of my second year I was sleeping with two women concurrently. One I met online. We’ll call her L (27). We had a phone conversation before our first date where she asked me what I was looking for. Because I was not above telling women what they wanted to hear to get in their pants, I said a relationship.
We went on a lunch date. She asked me if I wanted to come hang out at her apartment at the end of lunch. I pretended to demur, said it felt a little soon – though in reality, I had a condom in my pocket. She apologized and said she understood. I “reconsidered” and said I guess I had some time. So we walked back to her studio apartment in a nice section of the city. She was always home, worked as a marketing associate for a bra retailer – I swear I’m not making that detail up.
We drank wine, talked, and ended that first date by having sex. She called me “daddy” while I was inside her. That was a little odd, though also hot.Over the next week, L texted me a lot. Contradictory stuff. First that she felt slutty for sleeping with me like that on the first date, she’d never done that before. Later: “want you between my thighs.” She seemed confused about what she really wanted and this, too, turned me on. She asked me to come over on Thursday and I turned her down – I wanted to play the hard-to-get/did-not-really-need-her card pretty hard. I was also a workaholic who was busy editing my thesis film.
On Friday we did hang out at her apartment, again. She texted me before and said no sex this time, and how about we just get to know each other. I told her sure. But in my mind I knew that I could and would seduce her.
Hours later, I hit it raw, on her bed. She was okay with not using a condom because it was the end of her period. She called me daddy again, a number of times. I came inside her balls deep, propping her legs up in the air, without asking. I’d tasted blood while going down on her, but there was none on my cock afterwards, when I wiped it off in her bathroom. We cuddled for a bit afterwards, then had sex again. I left without spending the night, like the last time. But I did leave my watch there – she texted me about it when she was on the train.
The next evening, I resolved that I would just go out for one beer and that was all. I went to this place near my apartment and still impulsively sat next to the nearest decent-looking woman I could find. After a little while, she began talking to me. We had a decent conversation. We actually had common interests. We were both in grad school. She was studying for her Phd. in clinical psychiatry. The guy with her turned out to just be a friend.
After a while I asked J if she wanted to come have a drink with me at another bar. She had to “ask” her friend if it was okay. But of course it was (dude was kind of a sad sack). We had drinks at this other bar and I flirted with her a bit more heavily. I asked her at one point if she knew what I didn’t like about the tables. She did not. I told it was that they were too long, and if I wanted to kiss her, I’d couldn’t just lean over and do it. So I sat next to her and kissed her. We walked over to her apartment – which she owned, like a proper adult. It was clear that J was a bit older than me. I wasn’t sure by how much. She said she was divorced. I didn’t care. She pulled me close under a tree and kissed me with tongue. I get it: you can’t just go from a single casual smooch to a dude’s tongue in your pussy.
But in any case, I kneeled over her bed and ate her out. During sex, she scratched my back something fierce. Neck to ass. Might have drawn a teeny bit of blood. She made a comment about how lacerated my back looked when I came back from the shower, naked. This led to me making a comment about the Alanis Morissette song “You Oughta Know,” which led to us discussing how old we were when that song came out, which led to the revelation that she was ten years older than me.
We woke up at about 4:00 AM with one of her cats lying on my face. She shooed it away and thought it was funny and apologized. I was keyed up and wanted to fuck her again. So that’s precisely what happened. She rode me this time. It was dark and I could really only make out her bouncing breasts in what little light there was. This is what I was looking at when she stiffened up and squeezed me with her thighs and made yelping sounds. She rode me faster and leaned over to look right into my face. Her hair flew in her eyes, which were squinty, unlike her mouth.
Would you believe I did not actually cum?
I was spent. But that was both L and J in a leisurely 36-odd hour span. The next weekend was much more condensed.
I left early the next morning and said I’d had fun and wanted to see her again. We exchanged numbers. A week passed, during which I spent more time on my film and boasted to my close friend, (on whose couch I had fucked a nurse months earlier), about these two women in detail. I made plans with both L and J.
On Saturday of the following weekend, I went on a date with J. We saw a movie and came back to her place and played Never Have I Ever while drinking sherry and listening to vinyl. We made out on her couch and moved to her bedroom, where I suggested she sit on my face. She agreed, and I spent some time eating her pussy with my head craned upward between her legs. We fucked sideways on her bed and both fell off. We laughed. We cuddled.
The following morning, not long after waking up, I told J I wanted her again. We lay on our sides and kissed. In not much time I was completely submerged in her covers, head between her thighs, my feet sticking out from the back of her sheets. It would have looked comical to anybody who peeped in. Also pretty hot if you kept watching. I went down on her for a long time, using mostly my tongue, moving my hands around her body, occasionally up to her mouth. When I did finally move a hand under my chin to finger her – my tongue was focused on her clit by now – I couldn’t believe it. I felt nothing solid. All liquid. She was hemorrhaging fluid out of her labia. I still swirled my fingers around, let them slip against her thigh, which already felt wet. Her moans were all muffled through the sheets, so it was mainly sensory for me. I moved my mouth down to get myself drenched. Her vocals halted and her legs closed together and she jerked backward on the mattress.
I came up for air and kissed her and told her I wanted to do her without a condom. That made her face go from scarlet to a more uncomfortable shade. I told her it was fine, I had a condom. I still wonder how terrible it would have been if I’d persuaded her to let me raw dog her anyway.While fucking her, her head was cocked to the side. She was looking elsewhere. I said,
“Look into my eyes.”
She complied. She said,
“Fuck me.”
Which I was, uh, already doing…but I knew what she was really asking.
I went harder. She said,
“Harder.”
Faster and harder still. She said,
“Harder.”
As fast and as hard as I could.
“Harder.”
I went a little nuts (no pun intended!). I felt like I’d have a heart attack. Instead I just came really strongly.
We had breakfast and I almost burned down her microwave by putting a butter packet in there with the foil still around it. I went home and showered and puttered around a bit. Then off to L’s apartment.
L was in a very sassy mood. It was almost like she didn’t want to see me. When I texted her days before with a sexual innuendo, she’d told me to find someone else if all I wanted was sex. But she did not actually dump me. So I told her it was only a joke and continued to make plans with her.
At her apartment that Friday – some eight hours after J creamed on my chin – I tried kissing L and she turned her head away and said,
“Nope, I’ve already decided. Not today.”
We actually left her apartment this time. We had a picnic in the park. I decided I didn’t care if I didn’t fuck her this time. My plan was already to forget about her after today and keep things going with J. At one point, walking back to her apartment, I got distracted by some birds ( I was getting into birdwatching). She kept walking, ready to leave me behind.
…But I still sensed that sex with her would not take too much effort.
Back at her apartment, I still managed to coax her into a mood. She said,
“Okay, you can touch my vagina if you want.”
I did more than just that. I ate her out and fucked her against the wall and came hard. Again.
I did not forget my watch this time.
Two women in about 16 hours.
Later that night, my throat felt sore and my neck was whiplashed from all the cunnilingus. You see, when spreading L’s legs, I’d noticed this white gob dangling off one of her lips. Other guys would stop right there, I guess. I moved in and lapped that shit right up, and kept on giving her tongue. I’m pretty sure I licked up a yeast infection. So yeah, I’m disgusting and sort of kinky.
I did not sleep with either of them again. I stopped texting L and J broke up with me, saying she wasn’t ready to be seeing anybody. I moved on, and met my now-wife soon after. I’m aware that I wasn’t the most upstanding dude. I would say I was going through a phase. Still, I’ll never get tired of talking about this experience.
Source: reddit.com/r/gonewildstories/comments/w8o2lx/i_29m_juggle_two_women_2739_in_two_weekends_mff