I [M] then 24, obliged my female platonic nerdy friend [F] who was then 25, when she asked to be creampied…

I’m Jesse. My gf and I, who hooked up in our early 20s, went our separate ways into miserable marriages, are now together and couldn’t be happier and will use this account to post our stories where we were absolute sluts back in the day…and some stuff we’re experimenting with now.

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TL;DR at the bottom

Anyway, here’s my first post. Lisa, my gf, posted the story she told me that I think is really hot. This is her favorite of mine:

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In my mid-late 20s, I (M/45, now) was a complete fuckboy. I had a good job and made decent money, had an apartment with another fuckboy, and life was good.

Isabella (we called her Izzy) was a peripheral in our group for a few yrs, and every so often she’d be out with us. She never really seemed flirty, just friendly.She was a friend of the girlrfiend of another fuckboy associate, and had gone to college in my area and never moved back home afterwards so she didn’t have a big friend group.

She looked similar to the actress Rosie Perez; no striking beauty queen but not unattractive, either. She was Puerto Rican, abt 5’4, and very solid; a gym rat. She was flat-chested, not manly but muscular. Her belly was ripped, as was her ass and thick legs, abt a year or two younger than me. 

One night I was hanging at her apartment and I was telling her about how my girlfriend and I had broken up, not in an attempt to get in her pants whatsoever. I only looked at her as a friend and wasn’t even all that attracted to her in a romantic or even sexual way. She was one of the girls in our loose group and it could get complicated, and she didn’t seem like the type who would be down for a discrete ‘friends with benefits’ arrangement

She made a comment to the effect that I had to really ramp up my game.  I made a joke, saying “I’m gonna wear this out”, making a jerk-off motion with my hand. She had just taken some holistic massage therapy course (no shit, *eyeroll emoji*)  and she says how the hippy lady that taught the class showed them how to “release” a client. She kinda demonstrated on a hairbrush some techniques, and I told her what would feel good, we discussed lube, etc. She tells me that ‘she’s never done half of that stuff’, referring to using lube, handjobs, etc. The convesation goes on into the night, and relates that she has been with four guys: a bf in hs, 2 bfs in college, and the dork she dated the prior year from work. During the chat, she says “if you get blue balls because you ain’t getting any, I’ll give you some professional treatment”, winking.  The conversation still wasn’t really sexual in nature at all, though. It was an innocent joke, on her part….at least that’s how I read it. I didn’t get the vibe she was feeling me out.

So a few weeks go by, and I’m over her apart ment helping her move a giant fucking tv. It’s hot as fuck out, so she’s wearing a tube top and jean shorts (90s- fashion was often terrible). Again, she had a banging body but I hadn’t even given much thought to the conquest.  She ordered pizza and sat around her apt. After a few beers, she says, “can I ask you something, and I want you to swear to never tell a soul, but I need to know if you’d think I’m a slut”.

She tells me she that a couple weeks prior, she met her college ex for lunch, and he came over to see her apartment afterwards. She told him abt the massage thing, including the happy ending, and he asked for it. She said that since she hadn’t even seen a dick in almost a year, she massaged him and jerked him off, and he left. I asked why she didn’t fuck him, and she said he was a pig. I told her people our age gotta be a little sexually liberal, and she should’ve just jumped on it.

She then said she didn’t like fucking him bc it was “too big”, it hurt, and she didn’t have condoms anyway. She said it wasn’t like that anyway, and that it was to ‘relax’ him. I laughed and said, “Ok Izzy…whatever you say”.

I tell her that no, I didn’t think she was a slut, considering the complete lack of scruples I had at the time. I give her some scenarios of where girls are legitimately slutty (bless their hearts), and she seemed intrigued. It was now late, and I had work early, so I get up and moan about my back hurting from the TV, so she offers to  massage my back. I say “I’ll just take the handjob”, she tells me to shut up and lay down.  I do, now strangely turned on, and she massages me for abt 15 min, and by this time I gotta leave. I get up, and she HAS to notice I’ve got an erection I didn’t attempt to hide in my sweat shorts but she doesn’t mention it

The next day, we talk on the phone and she said, hey, I really appreciate that talk yesterday…I didn’t get to finish your massage. We joked about the happy ending again, and she talks about working for a legit masseuse. Before we hang up, she shoe-horns this question in there: “why don’t you come over here after work, I’ll massage you and you can sleep here while I’m at work.” (she was a hospital security supervisor).  Now, I had slept there a few times over the year or two we’d been hanging out, but it was often some of us just crashing there after drinking or whatever.

I still wasn’t getting the vibe; she seemed more awklwardly lonely than anything.

So after work, I get there and I get a shower (I worked in construction at the time and was sweaty and nasty) as I come out in a towel to get my bag with sweats in it, she asks if I’m cool with just a towel draped over me. I didn’t fucking care so I laid down on the mat thing in her living room with this small towel covering my ass, already hard lol, since she’s wearing these super tite and tiny gray cotton stretch shorts that showed *everything* and loose “gym” style weightlifting tanktop with no bra, so her tiny tits were just hanging there the whole time. She has the windows and balcony door open and the AC off, even thought it was fucking hot out.

She oils up my back and legs, and asked about my butt, if I want it done. I tell her of course; let me have the platinum package. So she gives me an incredible hour massage before telling me to roll over, and does the same for the front. She proceeds to give me an awesome massage, and as she’s doing so, she is kinda kneeling/squatting alongside of me, and I can see that she is quite wet (her light gray shorts are dark where her camel toe was).  Leaving the towel covering my waist, she moves her hands under it, oils me up and ends the session with the most awesome handjob (and I am not a fan of them) ever. Nothing spoken, and the one time I open my eyes, I glance at her, and she’s got this drunk-with-lust look on her face, sweating. It ends with me cumming onto my belly and all over her hands. 

I lay there on the mat, unable to move after 2 hrs of being massaged and masturbated, on my back. I’ll never forget this: She gets up, picks up the towel and stands, turns, and as she steps away, she dabs the tip of her tongue onto the back of her hand, tasting my load. This overwhelmingly hot thing about this is that she didn’t do it to be sexy; rather didn’t even know I was watching…I was lying there w my eyes closed and opened them as she stood up. She just wanted to taste it. She walked to the bathroom, and got in the shower. She had closed the door, and knowing her, I assumed she was done–the massage/happy ending wasn’t openly “sexual”, so I didn’t go in there with her. I wiped up with sticky load on my belly, put sweatshorts on, crawled into bed and passed out before she was out of the shower. 

A feel weeks go by, and she apparently kept quiet, as no one mentioned anything about us hooking up. We left a bar at closing, and she gets me alone in the lot and asks me out of the blue “are you cool with your massage—did you tell anybody?” I assure her that no one knows anything (I hadn’t said a word) and tell her again that it was the most relaxing experience I’d ever had! She said that she didn’t want to be known as a whore and told me that she thought she could trust me.

She was kinda excitedly babbling abt how she was sooo comfortable doing the whole thing, and how she wanted to do it again, and now that she knew I was “cool with it”, she’d like to “try some other techniques”.

She’s gotta work the next day, so we part ways but now I’m *really* curious to see how this goes.

Now that she’s “so comfortable” with this, she calls me every day, and now all she does is talk about sex, but like a curious teenager: what positions do you/guys like? What’s better:”oral sex” or “intercourse” (she was apparently a sexually inexperienced dork jock, and actually used those words), etc. I asked her about her big-dicked boyfriend (I’m average in a room of Irishmen), and she said “you only need 3 or 4 inches to feel it, anything more is a waste”. This immediately endeared me to her!

So a week or so goes by, until I ask her if I can come over for my “super massage” as she was calling it. She said “not for about two more days”; whatever. I kinda begged, but she was oddly not having it. So, me being the brat fuckboy asshole I am, don’t call her and blow her off. She calls a few days later and tells me “don’t make plans tomorrow nite, be here at abt 9” (I worked till 7).

I got done work, shower and head over there where we hang out for a bit, and have a few drinks. She’s wearing those basketball shorts (EWWW, fucking awful) and a tight  wifebeater tanktop, braless.  She lays the mat and a sheet down on her bedroom floor and drops the shades, making it very dark, but light enough that you could still kinda see once your eyes adjusted.

She tells me, matter-if-factly, to get totally underessed and lay down. She oils my back up and massages me. I’m face-down on this massage mat, but it’s obvious to me at one point when she takes her shorts off, and is wearing what I later learned to be a thong. She continues the massage, and we chat.

I ask her why I had to wait, and she says “yeah, I wanted to wait till you were here to ask you abt that…you can tell me no and I’ll understand, but I want to get a few things straight, and you need to swear secrecy”.

So of course, I do. She tells me, as she’s massaging my back, her friend (the girl who was dating the associate fuckboy) told her she loves it when he cums in her.

She tells me that she’s never even had sex without a condom, and goes on about how her friend describes the feeling, the warmth and wetness, etc of her boyfriend cumming in her. She tells me to roll over, and now I see she is wearing just the thong and tank top,She is now straddling/kneeling on/over me, rubbing my chest and shoulders, and she slides down (she had been sitting on my lower belly/pelvis, just above my dick) so she’s straddling my thighs. She’s rubbing my belly/hips/waist, and she tosses the little towel covering my rock hard dick aside.

She said really wanted to know what a bare dick felt like, and what it felt like for “a guy to ejaculate” into her (this fucking dork really did talk like this while giving me the most erotic massage ever). She then stops and says “this is going to sound crazy, but I don’t want to have intercourse with you but if I masturbate you, can you ejaculate into my vagina”?

Now, three things race through my head: 1) what a dork, using those terms, 2) she’s puerto rican: she’ll get pregnant, 3) what in the actual fuck did she just ask me to do? I’m confused.

She’s now sitting next to me as I lay on my back. So I first ask her is she’s concerned about, oh, I don’t know, getting pregnant, and how she didn’t know I didn’t have aids or something. She tells me that she knows I used condoms and that she didn’t want me to come over for the past few days bc she had her period and just finished the day before and therefore it was “safe”. As she is talking, she is rubbing my legs.

She climbs on top of me, facing away and is now straddling my lower belly, facing my feet, leaning over rubbing my knees, with her ass and pussy about a foot from my face, her soaked thong not quite containing her pussy lips. Quite an erotic position.

She reaches my feet, rubs them, the stands, turns, quietly and without comment , pushed her thong down her thighs and shimmies it off. She then straddles me so now she’s facing me again, and sitting on my thighs/hips, so my hanging balls are just touching her pussy, rubbing my hips and belly again.  I can feel on my balls her pussy is literally hot. 

I ask what she meant by “ejaculate into her without having sex”, and she says she’ll “masturbate” me sitting here (how she was sitting), and when I start to come, she’d move up, slide down onto my dick, I’d come, and she’d get off of me. There would be no thrusting, “fucking”, etc. She repeated that she did not want to “fuck” me, since she felt it would “change our friendship”, as she sat there naked, straddling me, her soaked thong next to me..and she was serious….DORK. I asked what she defined as fucking, and she said “like thrusting, kissing, changing positions, etc, to the point you climax”. She repeated she didn’t want to ever be a “fuck buddy”, but trusted me enough for this, and it was only to experience a bare dick and what a load feels like shooting inside of her.

I’m only slightly buzzed, and even as fucking turned on as I was, I was kinda nervous about this.

I was also in my mid 20’s, so….

She moves up now so she can rub my chest, and her pussy barely touching the tip of my dick. I say “be careful or we’re going to fuck!..3 or 4 inches!”

I asked her, as she rubbed, sitting here with the tip of my aching, thobbing, dripping dick just a fraction of an inch between her ridiculously wet pussy lips, how she could tell what was “3-4 inches”.  She said “when I feel the end of the penis on my g-spot”. I just look up at her, confused, and she rolls her eyes, leans forward so she’s on all 4s with her hands on either side of my head, and says “this”,  our faces an inch apart, and slides down, taking what seems like just the head of my dick in her. “Oooh…right abt there”, and then moves forward so it slides out. Her pussy was soaked and felt so warm. Just that second the head was inside her let me know that I was going to cum really quick.

I tell her “that was just the tip, though. I lift my hips, put my hands on hers, and slide my dick abt 3/4 of the way in and say “this is good, right here”, then I slid it out, my wet dick dropping back onto my belly. She said, “yeah, it is…that’s all it takes”. I asked if she could tell a difference w/o a rubber, and she said, “even as long as it’s been, yeah…it’s warmer and smoother”. As we talked and she was straddling me on all fours, my hands on the floor, against her knees. A drip from her pussy landed right on my dick–I’ll never forget that…

  I asked her exactly how fast she’d come right now, and what stimulation would make her come the fastest.

She initially got serious and said “it’s not about that right now”, but I told her it was hard to ignore her DRIPPING on my dick. She said that very light touches to her clit would do it, and right now, it would take seconds. “What do you mean?” I asked, and she lowered herself down so her exposed clit just barely was touching my dick, abt mid-shaft. She quietly gyrated, just barely touching my dick with her clit, in a circular motion, for maybe 15-20 seconds–wasnt long as all, and she silently tightened up, I felt her knees squeeze against my hips, trembling, and after abt 15 seconds she opened her eyes and kinda relaxed. She said “that was it, omg”, and laughed, her face flushed. I said, “You actually just came??” She said yeah, she said she “orgasms easily, and can have them one after another”. I could feel that the underside of the shaft of my dick was now very wet.

I asked her again if she was sure it was “safe”, and she said yes, and promised me that “even if something happened, even though it was impossible, I had nothing to worry abt”. I’m so fucking horny, I didn’t care what she said, I just wanted to cum. In her. Bareback. Now.

I told her ok, slide it in, I’m right there. She slowly slid down, all the way then up a bit so it was maybe 1/3 the way in. I grabbed her hips, pushed her down so I was all the way in, and let loose a fucking intense orgasm, staying still so she could feel it. I relaxed, said “that’s it” and she rolled off onto her side next to me. She said “that was wild–its warm and I could really feel it pulsing…it’s leaking out, and kinda opened her legs as she laid on her side, showing me the load drippng onto her thigh. She stood up, smiling giddy, and said, “yeah..oh wow…she’s right…definitely a difference”, and waddled into the bathroom, hand cupped between her legs.

We got dressed, hung out, got food and ran to walmart. The whole time she just babbled about how it was so “physical” and how she never solely focused on the sensations as she was always distracted during sex, etc. So it’s now getting late, like 1am, and I have to work again at 7 in the morning. I’m leaving, and I said “we don’t tell anyone, and never do this again, right?”, being the respectful fellow I am, as I’m making my way to the door. She says, “yes; I don’t want anything to change and no one to know…but was it fun?” I tell her it was so totally erotic…

She said that it felt good, but wonders what it would be like–if she could feel more pulsing (she liked that) if her vagina (her words, of course) wasn’t so stimulated from the orgasm she had only a minute or two prior, and if it wasn’t so deep.

So I said, well, let’s do your original plan real quick: I’ll lay down, you jerk me off, and hop on.

She says ok, and but she wanted to control the depth when I came. She’s naked in 2 seconds and has me undressed and on the floor. She strokes me, and it takes a while. I tell her I’m close, she straddles me so it only feels abt 1/3 in and waits, still, saying ” I want it here, on my g spot”. The sensation of the building orgasm subsides, I tell her “let me get there and that’s where it’ll be”. So I roll her over, and fuck her missionary for a few minutes until I feel my orgasm starting to build again. I quickly roll us back over, with her on top. She slides down halfway onto my dick as I explode again, inside her.  She tells me how “different” that was, and that she could feel more.

Exhausted, I get dressed, and went home…

Postscript:
She wound up having to abruptly move back home (several hours away) after her dad had a stroke…saw her once briefly after that at a bar, and got an email from her abt 8 months later telling me she was in the army and getting married…lol…ok…at least it wasn’t a baby pic.

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TL;DR: nerdy but built friend hears how sexy it is to have a guy cum in you and asks me to cum in her and not tell anyone. Of course, I did.

Source: reddit.com/r/gonewildstories/comments/apaix7/i_m_then_24_obliged_my_female_platonic_nerdy