Author: RolandLord

My [F]irst Affair – And [M]y First Phone Sex

I’d had plenty of opportunities to stray. Both in college and with the triathlon club, I interacted with a lot of attractive, available women and other than the occasional spank bank fantasy, never went a step in that direction. We’d had some challenges, a miscarriage shortly after we hit the five year mark, but didn’t let that get in between us. I loved my wife as much as ever, even during her distress.

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Note that I never really considered the dalliance with my neighbor to be an ‘affair’. Hell, we never even kissed! It was just a few erections (well, and a couple of orgasms) and that was that. Funny what we can talk ourselves into when we want to.

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However, years later, after the successful birth of our child, my wife started shutting down emotionally. “I have more important things to worry about.” that sort of thing. She literally said that to my face several times, along with “It’s not important to me to look nice for you.” She went from a drawer full of nice Victoria Secret’s things to three for a dollar Wal-Mart granny panties, for example. Yet she would spend an hour in the bathroom fussing about her hair before she went to a book club meeting or sewing circle, because heaven forbid another frumpy, flabby room mother would see her with a hair out of place. Read more »

[M]y Second A[f]fair – Part 2 – Her House [LONG]

A while back I told about my first sexual encounter with Anne, who eventually became my second affair. (I am a computer idiot, I don’t know how to link to that page.) I closed with her mention of ‘a next time’. Here’s what happened ‘that next time’.

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A couple weeks later I had just gotten home from caddying, and was alone at home. Showered, changed into clean clothes, wandering through the kitchen looking for something to eat. The phone rang, and it was her. She had seen me finishing up my round when she was playing tennis with one of her brothers, and knew I would be home. Her brothers and parents stayed for more tennis but she begged off and went home.

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So she, too, was home alone, freshly showered and hungry, but not for food. She asked what I was doing, and I told her. “Why don’t you come over? We can find something to eat here. We can sit out in the back.” I stammered for a bit, and she added, “I’ll be in my bikini….”

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[M]y Second A[f]fair – Part 1 – Stranger’s Backyard [LONG]

My first true sexual encounter was with a girl, I’ll call her Anne, first letter of the alphabet. She eventually became my second affair, so the preamble is important. We met one summer during grade school, we belonged to the same country club – 18 holes, two swimming pools, a dozen tennis courts, even a couple squash courts. We’d been on the same swim team, played junior golf in the same mixed foursome once in a while, even had squash lessons together one summer.

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One border of the club, where the line of tennis courts was laid out, bordered on a residential neighborhood, with the typical McMansions, big back yards, extravagant decks, some with pools, play sets, and so on. The houses didn’t have fences, due to homeowner association rules or it ‘simply wasn’t done around here’, I don’t know. Those along the 4th hole of the golf course, their yards abutted the fairway as this type of arrangement does. But the group of houses by the tennis courts had long rows of dense evergreens and other shrubbery to create some sort of privacy, who wanted to look out their back yard and see acres of cyclone fences surround the courts? Read more »

Busted! A neighbor’s [F]riend caught [M]e jerking off at a pool party (The Sequel, Part 2, The Disappointing End)

So she disappeared back into the bedroom to change, and I walked to the bathroom door that exited to the hallway. Just before opening the door, I adjusted myself. It wouldn’t do to have sideways tent pitched in my pants, particularly with Kendra having disappeared shortly after I did.

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I moved my erection so it was pointing straight up, under the line of my zipper, in order that it would stay supported and close to my stomach. I fluffed out my tshirt, hoping it would hide any visible ridge along the zipper line.

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Opening the door and leaving the bathroom, I was extremely aware of the meaty flesh throbbing between my legs, so I walked quickly down the hall, trying to distract myself. Upon entering the kitchen, her friends were all there, loud and boisterous as before, and they barely noticed me.

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I escaped from the house, grabbed another beer and a hamburger. Slathering it with sauerkraut, relish and onion, because I knew I wasn’t going to have to worry about kissing anyone that afternoon, I realized that while I’d seen her mostly naked and she’d had her hands on me twice, we’d still not kissed. That felt a little uncomfortable, but rather hot at the same time. Mulling that over, I sat back down. Read more »

Busted! A neighbor’s [F]riend caught [M]e jerking off at a pool party (The Sequel)

Some of you have asked about if there was ever any followup. Sorry it took so long to compose the followup. TL;DR: Took an unexpected turn.

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Turns out the Fourth of July party at the neighbors happened. I told several of you loyal readers that I brought her thong with me, just in case she would show up, but I didn’t hold out much hope.

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So I got there fashionably late, which turned out to be right on time, as there was a crowd that arrived right around the same time. We sat around and drank, and I casually looked about, to see if Kendra and her friend group was there, but no luck, not at first.

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Maybe a half hour later, though, a new crowd walked in, already wearing shorts and bikini tops, ready for the pool, and Kendra was among them. Unfortunately, there was a guy with her. That was a source of either concern or relief.

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Was it the boyfriend she ditched? A new boyfriend? Or perhaps he belonged to one of the other women and just happened to be talking to her. I’d play it cool and find out. Read more »

Busted! A neighbor’s [F]riend caught [M]e jerking off at a pool party (Epilogue)

(A lot of readers have asked ‘what happened next?’)

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So she was offering to hold my cock while I peed. This was totally not my style, I’m pretty open-minded about sex, but bathroom functions are private. On the other hand, I had to go really bad, I was about to burst, and reeling from the post-orgasm delirium, I relented to her pestering.

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I was still long and meaty, but my stiffness had completely subsided, so it was just a moment before I was ready to start a stream. “Ready?” I asked, and she pointed me toward the center of the bowl.

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The intensity initially surprised her, but she quickly adjusted, saying, “Wow, you really DID need to go!” Then she giggled, and started aiming the stream, around the bowl, at the center. “How do you not do this every time you pee?” She squealed in delight. “This is so much fun!”

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I just stood there, hands at my side, speechless. I mean, what do you say?

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Busted! A neighbor’s [F]riend caught [M]e jerking off at a pool party (Part 3 – The End)

I wrapped one side around my shaft, and gave myself a few slow strokes. I began to do the same with the other side string, when suddenly I heard a noise, and there was the door to the bedroom, partway open, with Kendra standing there.

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Oh-my-fucking-god.

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This is bad, how am I going to explain this, there was no where to go, she’s totally busted me, standing there with her panties wrapped around my hard dick. It couldn’t get any worse.

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And then it did.

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“Oh my god! You’re such a perv! I’m getting a picture of this!” and quick as a flash, she brought her phone up to eye level and tapped, before I could even register what she was doing.

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I looked down, even if I tried to cover myself with my hands, I’m standing there with my pants down at my ankles, there was no way out.

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“Holy fuck! Those are MY panties!” she exclaimed. She clicked again, and again. “You’re jerking off into MY panties?”

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Busted! A neighbor’s [F]riend caught [M]e jerking off at a pool party (Part 2)

I was stroking pretty fast, I needed to get this over with, there were enough people at the party that I was worried about hearing a knock on the door before I was done.

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Fortunately, having had this experience before, I knew I’d be able to make short work of this annoying erection. I was both extremely hard, due to the need to pee, and extremely sensitive, so it wouldn’t take long to bring myself over the edge. Already I could start to feel a bit of tingling in the knob, a for-sure precursor to orgasm.

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More to the point, that feeling was the whole purpose, it felt so good, the tickling around the knob, starting to focus at the tip. I could already imagine myself cumming, feeling myself explode over and over.

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But I wasn’t quite there, and that brought up the issue of where do I deposit my load. I wasn’t about to just spurt all over the floor, of course. Nor was I going to be able to aim at the toilet, I know I’d end up with cum all over the porcelain.

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A neighbor’s [F]riend caught [M]e jerking off at a pool party (Part 1)

I was at a neighborhood pool party over Memorial Day. The hosts were a family that were always at loose ends – that’s polite talk for saying their house was always a mess and the kids were wild. The dad was distant and often absent while the mom was the neighborhood flirt. You get the idea, right?

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So they host a Memorial Day pool party, they had an in-ground pool, with all the usual pool toys, and a large deck surrounding half the pool. As a result, most anyone who was in the pool would hang out on the deck still in their swim suit, but the deck was big enough that those of us who didn’t get in the pool were mixed in with those who did.

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There were two big tables on the deck, but only one with an umbrella. As I wasn’t going to be in the pool, and no chance to cool off, I parked myself under the umbrella for the afternoon.

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The wife was 20 feet away when our houseguest made me hard [MF] (Epilogue)

A number of people have asked if this was it or not, and, sadly, it was.

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After the sudden blowjob from Part 4, she’d started making more advances, but on the order of hints about how it didn’t seem like I was happy with my wife, that my wife didn’t seem to treat me very well, that she’d treat me so much better than my wife, and then along with those suggestions, stories about her past started to surface, how she’d tried to get between her coach and his wife. It became increasingly clear that she had an agenda to get me to leave my wife, and I was having no part of that. So we ended up having a huge fight after a particularly heinous scene.

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The scene? We had not been getting along, and it was clear she was not going to get her way. She tried to make up with me, and asked me over to her house. I went over, and her door was open. I walked in, and she appeared at the foot of the stairs, just wearing a long t-shirt, although really not that long.

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