Author: itasitwas

A Handjob by Any Other Name . . . [F21] [M21] [HJ] [BJ] [Str8]

Ashley (Ash) and I dated briefly my junior year of college. There wasn’t really any particular reason for the briefness (I suppose we just didn’t have too much in common), and we did have a very fun few months all the same.

Ash was categorically beautiful: blonde hair, hooded green eyes, and full DD breasts, not to mention a penchant for some of the dirtiest talking I’d ever heard. Witness, for example, something which was equally hot and (somewhat) amusing: Ash would refer to “handjobs” as “fist fucking.”

Anyway you look at it, this wasn’t exactly an issue: what difference does it make, and besides, I had to admit it made the foreplay even hotter.

One night Ash and I were watching a movie in the common area of the suite she lived in with a few roommates. Given that the lights were out (and no one really gave a shit, anyway), she and I began to fool around a bit. Before long, Ash had my cock raging at attention as she playfully stroked me over my pants while we made out. Correctly sensing that the movie was no longer the main feature, Ash soon stood up and led me back to her room. Read more »

CONTINUED: The Best Kind of College Reunion [MF] [MFF] [Str8] [Les]

After soaking she and Kim with her explosive, squirting orgasm, Julie eyed my again-hardening cock. Excusing herself briefly, Julie said “Umm . . . I need a break, but don’t go anywhere,” as she made her way to the bathroom to freshen up a bit.

As I watched Julie walk away, Kim slid up the bed to me. “That was fuckin’ amazing,” Kim said; I had to agree. “Honestly, though,” Kim continued, looking me
right in the eyes, “if I’d thought anyone was going to cum on me tonight, I’d have guessed it would be you.” My cock pulsed slightly at the thought. Leaning in for a kiss, Kim said, “or possibly in me.”

Kim and I started to make out as she grabbed my cock and stroked it. It didn’t take long at all until I was fully throbbing, my cock reflexively starting to fuck her fist as she stroked me slowly. “I hope this isn’t too much,” Kim said, “I just have to admit I’ve been thinking lately back to when we fucked that time at your place, and I’ve been fantasizing about what it would be like to fuck you again.” I told her, of course, that not only did I not mind, but that I too had been reminiscing about her and her tight, athletic body. Read more »

The Best Kind of College Reunion [MF] [MFF] [Str8] [Les]

Like most people, I’d be lying if I said I was looking forward to my ten-year college reunion. Not that I had anything in particular to dread, but rather I’m just not the type who generally enjoys all the small talk and “catching up” involved in reunions. On the other hand, I’d also be lying if I said there wasn’t something in particular piquing my curiosity as well.

​

Let’s just say the curiosity won out, and when that invitation came, I was quick to RSVP.

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I had reason to believe that two of my old friends—Kim and Julie—would also be in attendance. The three of us had an interesting history; since college, I’d had the pleasure of spending some intimate time alone with each of them (Kim and I hooked up after a party once, while Julie once helped me though some relationship issues with an extremely intense evening), but it was actually something else which had me excited to (hopefully) see them at the reunion.

​ Read more »

Making Work Conferences Fun [MF] [MFF] [Str8] [Les]

On the grand list of bullshit jobs one will work in a lifetime falls a job I had about ten years ago. On the whole, I don’t suppose it was all that bad, really; just a lot of tedium and boredom mixed with occasional bouts of extreme stress.

So, a job.

That said, most of my co-workers were in their mid-twenties like me, so there was a fair amount of screwing around and socializing when the managers weren’t around (or–more often than not—hiding in their offices). A few months after I started, Michelle and Amber started. At first, they mostly kept to themselves and didn’t engage much with the larger group. Soon enough, though, they were paling around with the rest of us.

The three of us formed a somewhat tight bond. As the only male in my department, I was something of a novelty, which I suppose Michelle and Amber embraced. Before long, the three of us were hanging out outside of work as well.

Both Michelle and Amber were fairly attractive, and I have to admit that was never lost on me. Most interesting was that—-from time-to-time—our banter would turn flirty (especially when we weren’t at work), but I never read too much into it . . . until we all three attended our first off-site work conference together. Read more »

A Summer Night Making Up for Lost Time [MF] [Str8]

Dorothy was a spectacular woman I dated for a few months during the summer between my junior and senior years of college. Although we only dated for a few months, we’d known each other for several years and I’d had a crush on her for some time, so I was excited to see if we could be something more than friends.

Dorothy and I met up for coffee one evening that summer at a place near her apartment. We’d been seeing each other for a few weeks, and I was generally really enjoying our dates. I’d just broken up with a mutual friend a few weeks before Dorothy and I started going out; that fact wasn’t strange for me, but I sensed it was a bit for Dorothy.

In any event, we met for coffee that night, and we got on the topic of sex. She very casually commented that she’d been told by previous partners that she was really good at giving head; I replied that I’d been told the same of my own skills. I liked where this was going, but at the same time I couldn’t believe my own good fortune. Read more »

[MF] The Challenges . . . And Opportunities . . . Of a Long-Distance Relationship

As someone who’s been there, I suggest you tread carefully when it comes to maintaining a long-distance relationship with your significant other. In my experience, the most important aspects of a healthy relationship erode over time as distance extends . . . except for the sex.

My friends, this is a story about the sex.

Sarah and I met through mutual friends just as we were about to both graduate college. Although we felt a very strong attraction, we had both resolved to move to different post-graduate cities. This left us with daily phone calls—wherein we mostly argued—and weekend-long visits.

At first, there weren’t any red flags: Sarah and I had a great relationship when we were together in-person often, and we thought the physical attraction would bridge the long-distance gaps. Honestly, it wasn’t a bad plan from my perspective: Sarah had a thirst for sex and a body round, soft, and tight in all the right places. Moreover, she really knew how to use it, not only for her own pleasure, but for mine as well. Read more »

[MF] Being a Pawn in Her Game Wasn’t Too Bad.

Casey lived with Julie in the rundown apartment I mentioned in a previous story. Although I’d known Casey for some time—and we had many close friends in common—we’d never really spent any time alone just the two of us.

One evening I knocked on their apartment door, and after announcing who it was, I heard Casey’s voice from somewhere within, inviting me to let myself in.

When I opened the door, I saw Casey on the opposite side of her living room, standing in nothing but a towel. Although taken aback by this, I did my best to play it cool, pretending that Casey was fully dressed as I had (reasonably) expected her to be (especially given her usual shy personality). Still, I had to admit to myself that there was an exciting sight before me; Casey was the most fit of all my friends, and was somehow perpetually tan. I couldn’t help but steal a few glances at her toned legs and the hint of cleavage peaking out from the top of her towel. Read more »

[MF] From Friend to Fan to FWB

Emma and I came up in the same hometown, but our adult lives couldn’t have been any more different. While I’d always vaguely flirted with the idea of a career in the arts, Emma was actually making it happen as a photographer.

Still, our friendship remained intact as her success grew. One fall afternoon, Emma stopped by my apartment to visit me. We spent the afternoon exploring before returning to my place with some Chinese carryout for dinner. Since my roommates were home, we set up to eat on the floor near the foot of my bed in my bedroom.

Although I’d never really thought too much about Emma sexually (save for a few instances where—I’ll admit—I jerked off thinking about her just for fun), I can’t deny that there was something very attractive about her that evening: her artsy style (large-framed glasses, shoulder-length brown hair, a dark sweater, and a flannel skirt) went well with her somewhat slight frame. Read more »

[MF] Old Friends Give the Best . . . Advice.

After college graduation, my friend Julie moved into a old rundown apartment with a few of our mutual friends. Because her place wasn’t too far from my own, I frequently stopped over after work (occasionally bringing dinner, being the great guy I am).

Such was the case one night when I stopped by the apartment. Around this time, I’d been dating a women for a few months; as I recall, we were having a rough patch around sexual compatibility and had recently decided to take some time apart. I remember lamenting this to my friends as we ate, and they recommended I get advice from Julie (who had thus far spent the evening in her bedroom).

Finding Julie’s bedroom door shut, I gently knocked. Julie’s startled voice called out asking who it was, and I identified myself. “One minute,” she replied, and I heard a drawer quickly open and shut. “Come on in,” she then called.

I opened the door and saw Julie sitting at her desk, across from her bed (which was surprisingly not made; strange for her). She was a little flush, but smiled as she gestured for me to come in. Finding no where else to sit, and honestly not thinking too much about it, I took a seat on the bed across from her. Read more »

[MF] From Platonic Friends to Make-Up Sex

Those first few years of my early twenties felt much like the college years before them: I didn’t move too far from my college town—and neither did many of my college friends—so we mostly stayed in touch and continued hanging out.

Although we were all making our way in the world, that didn’t mean we were suddenly different people. With no one was this more true than Kim.

Kim and I had been friends for a few years, but—as one might expect—our graduation trip the year before had changed things a bit. Although we’d never really discussed that night of mutual masturbation we shared, but we both clearly never forgot.

One night after a party in my apartment, Kim and I had some sort of stupid argument (as friends sometimes do), and we ended up alone at the end of the party to talk it out. I ended up next to Kim on the couch with my arm around her, likely consoling her over whatever it was that was really bothering her. Read more »