My RAOBJ was a boring date but a great fuck [FM]

I can’t say that many of my boring dates led me to swirling my tongue around a good load of sperm, but I do love a good exception to the rule.

The thing with RAOBJ dating, to call it that, is that the promise of sex salvages otherwise boring meetups. On Tinder, this date would have ended with polite excuses as soon as we split the bill amicably. But this time we lingered after one too many awkward silences, after a rather boring conversation, if only because he knew I’d be down on my knees and sucking his big dick.

It was only fair to assume that… since I had advertised it on Reddit.

I know no one is surprised that it turned out to be so boring in practice, but I honestly was. On paper, everything had looked good: he was handsome, successful, likely single, kind, and horny. The only thing missing was, well, IRL chemistry. That should have ended the date at the bill, shouldn’t it?

But I was horny, so was he, and we needed to get off.

[FM] Drilling McDaddy (A Pegging Tale)

On a warm August night last year at my favorite inn on the north side of town, I gave my new FWB McDaddy a proper buggering for the first time.

McDaddy, just separated from his wife, had recently achieved silver fox status in my eyes due to some cosmetic improvements and was really starting to enrapture me. Yes, OK, he was still in a state of long-term unemployment. And yes, he was temporarily homeless too. But hey, at least he looked good, had weeknight availability and was adventurous too! I wasn’t in the market for a husband after all, just a fun fuckboy.

And fortunately for me this particular fuckboy was down for some pegging.

I was pretty amped because 1) I find pegging to be empowering AF and 2) I already owned a designer harness that I’d used on just one other person at that point.

My harness was shimmery and sliver and had a fur lined interior. I’d bought it at a sex shop in D.C. so whenever I wore it, I felt like a leader of the free world understandably. And I was especially excited to see how it would look with the hot pink dildo McDaddy had brought with him that trip.

[F] STUPID SLUT CLUB

I’m always early, which is maybe a terrible thing, but most of the time I’m on time and everyone else is running late. He[M]40 and I used to work together, so our friendship is relaxed. We’ve played D&D together before, and I know his wife 38[F]. She usually attends our sessions (playing sessions, don’t get dirty yet), and if we tell folks to arrive at 7 o’clock, most arrive by 7:30.

Exceptionally, lol.

As a result, I would arrive on time, assist with setup, lay out coasters and glasses, and clean up after myself because, as I mentioned, we are friends and I am comfortable with their home. He was engaged and later married, so I didn’t act on my suspicions of tension or attraction when we were direct employees. Never straying from the rules and always acting professionally.

Several months ago, I arrived promptly, helped set up as usual, and made a joke about how there wasn’t much to do as we waited for everyone else. As I pulled coasters out of their kitchen, I heard him enter from behind me. Again, hardly extraordinary. I need to get the whiskey and water for our game. To my astonishment, while I was choosing the coasters, he rubbed against me and remarked, “We could make it less dull,” while going for the whiskey on the shelf.

[M] I sat and watched a friend get their big clit hard for me.

I went to see my sister and her wife the other day. While I was there a friend of theirs turned up who was transitioning from female to male. Although he wore men’s clothes and had a mans short haircut he still looked very feminine even with patches of 5 o’clock shadow around his chin.

He had been on hormone therapy for some time as is due a mastectomy in a few weeks but seemed extreme due to him being quite flat chested anyway. He is hoping for his genital reconstruction soon after.

It was interesting to hear how he made the decision and all the things he has had to go through to get this far. I was fascinated with how his body had changed due to the hormones. He said his voice had deepened but it was still quite light to me. There was the obvious increase in hair growth on his face but he explained it was now thicker on his arms and legs. No chest hair though. He said the most noticeable change was his clitoris. He said his was already quite big but now he could play with it like a little dick.

Chastity B-Day Pt 3

Now as I mentioned before I do wear skirts at home because I find them more comfortable than pants while in chastity. Which actually means I own more skirts than jeans since I work from home. I had never considered being completed dressed feminine. You know the saying happy wife-happy life, besides I wanted to know where all this was going. In all these many years I had never seen this side of my wife.

My biggest concern was how to put on pantyhose without ripping them to shreds, I must admit at first I tried to put the bra on first then hook it in the back until I remembered how my wife put hers on. Also the falsies kept falling out until I realized that’s what the medical adhesive was for. Oh yes I tried to just take the wig off the styrofoam head a couple times then just held the base and yanked, pins went flying all over the place. I have to admit when done and I looked in the mirror my thought was I get why women like to dress this way as it looks better than the standard white, black and brown us men tend to wear.

[MF] Putting the temp room to good use

Rotating through hospitals is part of my job and sometimes I might have to stay late, or be there early for surgery. Luckily, at one of these hospitals, they gave me an on-call room to sleep in. One particularly cold month a few years ago, we were snowed in due to an incoming blizzard. I had my wife waiting for me at home, she would have to wait some more because it was too dangerous to drive in the rural Pacific Northwest in that storm. I spent my time in the ER talking to some nurses, keeping ourselves entertained with stories ranging from our favorite movies to scariest experiences in life. As a horror movie nut, I try to keep an open mind regarding supernatural experiences. And the moment I started talking about haunted hospitals, everyone’s eyes lit up, and they began frantically sputtering about the morgue.

“Oh dude, you definitely should not go down there,” the cute travel nurse said. But I would not be deterred. I’ve never had a paranormal experience in my life, and while i’m not a thrillseeker, this particular place did not seem overly evil or gav me bad vibes. So I asked If someone would accompany me to the morgue just to see from outside. Pin drop silence, and suddenly that travel nurse volunteered.

My first hotwife experience [MF]

A few years ago I was in a London pub on a Friday night and wound up talking to Kiera. She was dressed well, classic black number, gold ear rings and a delicate necklace that subtly drew the attention down. She had a great figure, full and curvy, and was a little older than me which was a nice surprise. I’d always had a thing for older women but never really got the chance to talk to them.

My friends had moved on to the next bar so we were left alone. The conversation was fun. She was eloquent and witty, and things were getting a little bit flirty. She explained she was visiting for work, asked me what the dating scene was like in london and wanted fun stories about nights out.

We’d been sharing a bottle of Malbec and carefully inching closer to each other as the night meandered on, and it was only when she went to pay that I noticed a flash of silver on her left ring finger.

“Is that a wedding ring?” I asked, slightly shocked.

“It is,” she replied with a hint of a smile.

The Mormon Apostate and the Bishop’s Wife [M|F, 18-30s][religious innocence][exhibition]

**Title: The Apostate and the Bishop’s Wife**

“Bishop James, hello.”

“Brother Smith! Well gosh, I’ve been missing you. I –”

“I’m gonna stop you there.” It comes out louder than I meant. “I came to church for one reason.”

Everyone in the foyer looks at me. I didn’t mean to draw a crowd, but fuck it. “I need to tell you to your face that I’m done with this Godforsaken church. Mormonism is bull-fucking-shit and you are a fucked up, power-hungry, overly-chastity-preaching cancer for all these people.” I turn to his wife. “You deserve better.”

I feel like I’m floating as I leave, and I can’t suppress the grin. People talking – about me and to me – are muffled noise.

As I’m opening my car door, she calls out. “Shep!”

“Oh – Sister James. Hi.” She cuts across the lot at twice the speed I did, “What are you –”

“Call me Julie.” She catches her breath. “Please.”

“Right. Julie.”

“You – that was amazing.” She pauses. “What you said.”

miiiiightve just done one of the sluttiest things ive done yet [26F]

i was incredibly hormonal and awful this afternoon; my fiancé had had me suck him off the night before, and it had gotten me so so wet. when i asked him to get me off, he refused, and eventually i fell asleep dripping and incredibly unfulfilled. as a result of that, i picked a dumb fight while i was at work and blew up at him. i knew if i was gonna have any fucking hope of keeping myself together, i had to get fucked.

while i was at work, this guy came in, wearing a wedding ring but absolutely flirting with me. i was wearing a tiny lil black semi see thru crop top (no bra), and a tiny lil wrap around plaid skirt that had a split almost up to my pussy (no panties) and obviously made a point to bend over to show off for him. i passed him my # in his purchase, and not even a full minute after he left, he was txting and asking what i was doing after work. i replied “u 😜”. he told me that if we were gonna do this, we’d have to be so so so careful because – get this – he would have to host me because his wife would hear if he left but id have to be so quiet.

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[MF] My blessed second marriage to a gorgeous and horny ex-stripper

I posted an earlier version of this under another account. Now that I’m back, here’s an updated version.

So yeah, it’s been a rollercoaster. In 2018 I took a job overseas, in Milan. My wife and I moved out there and it grew on me more quickly than her. Other tensions were present as well, and we decided mutually to split up in early ‘20, it had been coming for a while and we both knew it wouldn’t survive lockdown.

During the same period, I became gym-buddies with a gorgeous, twenty-something, whip-smart (engineering degree!) tattoo-covered stripper with an absolutely obscene body—skinny waist, round ass, huge tits and (I later learned) a penchant for pairing denim jeans with translucent tops. She liked me because I was just about the only guy at the gym who wasn’t either leering at her or hitting on her. We started chatting one day and we hit it off. Of course, I never dreamed a goddess like her would see our friendship as anything more than platonic—I felt she saw me as a “safe” friend, and (being in my forties at the time) I probably reminded her of her dad. (I was right, but that was not the barrier I’d assumed it was.)