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Multiple Spring Flings

How I became entangled with two women at the same time one Spring during my troubled years

This is going to be a long one, so if you aren't into reading a fairly involved story then maybe this isn't for you. And this is only part 1. But I know it is (was) hot for me when I experienced all this, so my hope is that others will think it's sexy/entertaining. Just a couple questions for people who finished at the end.

I am settled down now (thirty-two-year-old male) and engaged but I keep mentally remembering the spring of 2016 when I (then a twenty-nine-year-old male) became involved with two women during an overlapping period of time. I was finishing up my grad school thesis at that time and had a pretty big ego about it. I felt fairly overconfident and was going through quite a promiscuous phase. The long work hours I put in seemed to culminate in these bursts of sexual mania that I hadn't felt since I was an undergrad in college (some other good stories from those times, too). Via OkCupid, Tinder and the bar scene-- I was also drinking a bit more than was healthy--on breaks from working towards my degree, I would go out and desperately seduce whomever I could. Sometimes I was completely unsuccessful; sometimes a woman would respond to me. I wasn't going to quit any time soon.

Through OkCupid, I met a woman named Lauren (twenty-seven, I think), who I exchanged messages with and eventually started talking with on the phone. She wanted to talk with me before our first date to make sure I was legitimate. As I walked to meet her at a cafe in Chicago on our first date, she sent me a text with a picture of what she looked like. In the picture, she wore a tank top and short shorts that accentuated her thighs. I sensed that she felt horny and desperate, kind of like myself. At the same time, I wondered if she was a serial killer. I decided to see what happened.

We met and she seemed normal. Looked like her pictures, had a tattoo on one arm, made good conversation. She asked me at one point if I wanted to come back to her apartment to hang out. I at first told her I would have to think about it and that I didn't usually get asked that on a first date. She was apologetic and said she totally understood if I didn't want to.

If you are wondering if I was simply playing somewhat hard to get, then the answer is yes. If you are wondering if I had a condom in my pocket, the answer is yes. I ultimately decided to go back to her place. She lived in this fancy, but dim studio apartment. We drank wine and watched Friends. At some point, I kissed her and she seemed a little startled. But one thing led to another and we ended that first date by having sex on her bed, missionary position, her calling me 'daddy' while I moved my cock back and forth inside her. It was a little awkward--most first sex is--but we had fun. I did not spend the night. I left with promises to hang out the next weekend.

In the intervening week, Lauren sent me a lot of texts. Some were to tell me completely mundane things, like that she was getting her nails done. She worked from home as a sales agent for women's lingerie, specifically bras. She wore a lot of makeup and glittery lipstick and from what I had observed the past weekend, already had her nails done to last her a lifetime. She was very fashion-invested; this was not like me at all. Her texts reminded me of that.

Other texts said things like: I want you inside me. I had never met a woman who was so forward like this and it was a real turn on. Somehow, though, before I went to her place the next weekend, she texted me: Let's try not having sex this time and just get to know each other, K? I thought, 'Bullshit, I am going to get you in bed.' I knew it wouldn't take much effort.

When I went over there the following weekend, she made sure I took off my shoes before even setting foot inside--she was also a neat freak, you see. I brought a cheap bottle of wine. She reminded me that we shouldn't have sex this time, and remarked that she felt slutty about just sleeping with me like that on the first date. So we did our rigmarole of casual conversation and watching TV and drinking wine. We did both like wine. That we had in common.

I kept casually flirting with her as the day progressed and she responded with certain remarks; she said I seemed like I'd probably been with a lot of women whereas she'd only been with a handful of guys, asked me if I liked getting blowjobs, etc. Eventually, I had my hand on her thigh, stroking her calf over her jeans. She muttered, stop that, I was making her horny. I asked her why that was a bad thing. I leaned in and kissed her.

In not too long, I was going down on her. She had a large, easily wet vagina. I remember she said she'd just finished her period and I tasted a faint bloody taste. She kissed me after and said with a laugh that she tasted herself. Then we fucked, then more TV and wine.

We were both still horny. We had some brief, cursory conversation about how she was on birth control while rolling around on her bed and she said we could go this time without a condom. I entered her bare. I'd had plenty of unprotected sex about nine, ten years before, but this was me just being reckless. I started off slow.

When I heard her whimper, 'Daddy...daddy...' I started to, quite suddenly, escalate the intensity of the sex. I recall feeling her get wetter and wetter. And oh, the sounds of rough sex! Mattress squeaks, wet whapping noises competing with excited female noises. Hearing her react, watching her react, and feeling her on my cock made me realize how rough I was giving it to her. She arched her head back on her pillow and went, "AAAHHH!" I came inside her. We cleaned up and kissed and I left.

The next day was Saturday. I was at work on my thesis again. I thought a bit about Lauren and how I'd just raw-dogged a relative stranger and wondered if any of her previous guys had given it to her like that. I had left my watch at her place, which she'd already texted me about. So I was definitely going back there next weekend. But would we keep things going after that?

I decided to go to a nearby bar for a drink. Just one drink, I told myself. I got there and, telling myself I had no plans to meet anybody new, sat at the bar next to a woman wearing a purple blouse and fancy scarf. She was with a guy who I assumed was her boyfriend. I drank my beer and minded my business and eventually, she said something to me. Something like, did I come here often? I said I'd been a couple times and liked their craft beer. We gradually slid into conversation.

Unlike Lauren, this woman was capable of interesting conversation. More capable than I was, I think, though I wouldn't call it a weakness of mine. Like me, she read books and liked movies. We talked about our families, our grad-school lives--she was also in grad school, for psychiatry--and everything else. The guy next to her slid out of the picture. He sat there drinking, looking not that surprised that she was talking to me. When he went to the restroom I asked her who he was. She said he was a friend of hers. They'd just seen the Amy Winehouse documentary in a nearby theater.

Her name was Amy. I would learn later that she was thirty-nine, a full ten years older than myself. She had freckles and sandy brown hair. I could tell she was older and that attracted me. At some point, I asked her if she wanted to go to another bar with me and have a drink. She had to think about it and asked her male friend about it. I felt confident that she would agree. And she did.

At this other bar, we sat at a table to ourselves, drinking cocktails. I made constant eye contact with Amy as I listened to her and talked to her. This was my only real method of seduction in those days: don't drop eye contact and it will woo her in. At some point, Amy mentioned that I made good eye contact; score one for the Method! I told her that the problem with these tables was that they were too big for me to lean across and kiss her. She blushed at that. I went to sit next to her. I kissed her. She kissed me.

In the same way that Lauren probably didn't guess that she'd fuck me raw the day before, I didn't guess that there would be long, pointy fingernails tearing down the length of my back from neck to butt later that night. I was moving steadily in and out of Amy, on her queen-sized bed in her beautiful apartment. Her passion seemed outsized for the gentleness of the sex. Sure, I'd gotten her worked up by going down on her first, but still. She moaned with each stroke of my cock and scratched my back again. Yes, it definitely hurt. No, I didn't say anything. I was into it.

I hadn't, of course, brought any condoms with me this time--I've never been just a straight-up condom-walker--but she had a supply. I sped up just a bit. I sped up some more. I listened to her pant and staved off my orgasm for as long as I could.

Pantpantpant scrrratch.

Afterwards, we took our respective trips to the bathroom and lay in bed. We talked some more and cuddled. We fell asleep only to be woken up a few hours later by her cats, which had been very annoying all night. In a way, they didn't have to wake me up. I was completely keyed up anyway. I didn't want to fuck again; I craved it.

Amy dealt with her cats and apologized for them. I started massaging her chest. She wore a plain white t-shirt and nothing else. I was completely naked and very hard. I kissed her face and nibbled her ear and moved my hand around her body. She was into it. She wanted me to. I finally slipped a couple fingers between her thighs and over her mound. I dipped them into her labia and worked them around in circles. Amy's breathing picked up. I fingered her a little deeper. She moved her legs around.

The next thing I remember is her riding me in the dark, illuminated by some moonlight. I held onto her hips and helped her bounce her body up and down. Maintaining constant eye contact now wasn't as easy--I had to strain my neck to look into her face. So I looked away from her face and focused on her tits. They were nice, rounded tits with hard nipples. I slid my hands a little further up her torso to get them closer to her tits. I bounced her a bit harder.

Amy panted and gasped in an increasing crescendo. This crescendo ended with her yelping in these drawn-out bursts followed by hyperventilations. How do I write it? Something like "UuuHHHAHAH...AH! UH!"

She stopped bouncing for a moment and squeezed my waist with her thighs. Then she kept riding me, fast and hard this time. I looked into her face. She was bent down closer to me now, a hand on her headboard, another on my shoulder. Her hair flew in her face and her freckles scrunched up on her open-mouthed, squinty-eyed face.

We talked a little more after that. It was then that she found out I was ten years younger than her. She seemed to feel almost guilty at having sex with a guy who had been in fifth grade when she was a sophomore in college. She remarked on the long scratch on my back. I told her, "Yeah, I'm pretty sure that was you."

The next morning--not too many hours away--I woke up first because I'd set an alarm. I had a job on a film set. I was very under-slept. Amy and I exchanged numbers before I left and agreed that we'd had a good time and should see each other again. I planned on waiting a couple days before I texted her.

 

While on the film set I received a text from Lauren. It said: Want you inside of me. I didn't respond to it for the time being. I focused on my job.


 

(This is the end of PART 1. Part 2 will be posted shortly. If you feel like stopping here, it's cool.)

 

 

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