The time my fwb/ex convinced her friend that I would be a great judge for a BJ contest [MF][Cheating]

Dear Penthouse Letters…

Ok well honestly I’m a little too young to get that reference but still old enough to read a ton of erotica that started with it, satirical or not. Either way, the following is true, no I can’t prove it… I was a good Christian kid who’s dad had found his porn stash one too many times so I stopped keeping evidence.

This story is about Anders, and how she somehow convinced me to judge a Blowjob contest while I was dating neither of the contestants. Anders was the type of girl who was able to charm their way past just about anyone. When I first met her I was your typical quiet Christian cult member. (Think Mormon, but we called ourselves “non-denominational”) I’d been porn free for almost a year, I denied the deep seeded perversion growing within me, and there was no way I was going to get married without my virginity intact. Anders had different ideas. Within a year of meeting she was my first girlfriend. She spent the whole first date innocently grinding on my lap, the second date she didn’t stop until I’d accidentally came. A date later she my first hand job, within a few weeks my first BJ was surpassed… hell within the year we dated she was everything except my first PiV, but due to the emotional attachment I still consider her as the one I lost my virginity too.

I had four [f]irsts in the sa[m]e night

* five

It’s also my first here and I hope you’ll enjoy!

We met up shortly after texting for a week.

Before that, we spoke on the phone. He made me laugh and I felt like I could talk to him forever, it just never gets boring. I was almost completely over someone else and thought it’d be good to get to know someone new. He knew I was a virgin (although I had a dildo, so not much hymen left).

Upon meeting up he was very nice and authentic. I’ve never met someone like him. We talked for a few hours and I was adjusting/trying to relax.

Anyways, we went out along with a bottle of white wine to a historical building surrounded by fields. This place had a balcony and we were completely alone. We were making jokes, teasing each other and drinking. Both started to get tipsy and he started putting his arm around my waist while I leaned on the balcony. After some more talking, he put our wine glasses away, looked at me, ran his hands over my neck, breasts and waist, said he liked me and kissed me. I am super sensitive and kissing is enough to make me wet. I started moaning almost immediately, he said he liked how I kiss.

Lost a bet, gave a bj [FM]

So about a year ago I met this guy Tyler. He’s my sisters husband’s friend from the military. As soon as I saw him, i thought he was so sexy. We meet at a party my sister was having, we exchanged numbers and talked and video chatted a bit, flirted. Anyways I’m a cowboys fan and hes a philly’s fan, he’s from there. He bought tickets to a Sunday night football game, and asked if I wanted to go with him, and of course I said yes. So Sunday afternoon he picked me up and we went tailgating. It was so fun. I loved feeling his little touches. He’d occasionally grab my ass, caress my back, had our first kiss it was nice. We got a little tipsy, and as we were waiting in the tail gate area we were flirting a bit. He said we should make a bet. I agreed and he told me he wanted a bj, if he won and if I won he’d eat me (which he did regardless) anyways I laugh but agree. We go to the game and hes very handsy. I lose the bet and as we’re walking out he says dont worry babe, I was jk. We casually talk and get to his truck. We’re in his truck and stuck in. He says so the bet and laughs. So I pick up my hair lean over and pull out his BBC. I end up going to work, having him feel on my ass. I worked him about 15 mins until I got my reward. We ended up at his place after. But it turned me on so much and made feel so slutty. He recently text me as he is on deployment. :(

My first time with a tgirl [MT]

This happened over 10 years ago after I had dropped out of college and was trying to “find myself” so the details are hazy, but I wanted to share it because I still think about it to this day. I still jerk off thinking about how hot it was.

Some backstory… I grew up in a pretty big city (I won’t tell you which one). After high school, I went to a state college that was about 3 miles away from where I grew up (I wanted to be a teacher… I didn’t become one, but that’s a different story) and my dad died suddenly when I was 21. He was diagnosed with cancer and the doctors said he had a really high survival chance but he was one of those weird cases where he suddenly died about two weeks after the diagnosis for what seemed like no reason. I’d gotten about $30,000 from his will when he died and just didn’t feel like working or going to school. I was really lost.

The first time I [m] sucked dick [mf]

This happened in March of 2018

Over many years I’ve had a recurring fantasy about being with men and/or trans women. I would push this away, since “I’m a straight male – not interested in that, and married with a child…” and all the reasons I wasn’t gay. While at the same time, 95% of all my male friends were gay.

Over the last few years, these fantasies happened more often, and stronger. A couple weeks ago, my lovely wife and I had a conversation that changed my life. In that conversation, she helped me come to the realization that I like men and women (and at least trans women, if not all trans probably). She had known for years, but never wanted to push. She told me that while she would support me in exploring this, and I could talk to her about it, she wasn’t interested in exploring it with me. So, I was free to explore outside our marriage.

From this conversation, I felt at ease in a way I haven’t in a very long time. I started watching the things I’d been avoiding for years. I kept checking my reaction to different videos, pictures and writings. Come to find out, a lot of it turned me on.

Jessica Emerges [crossdressing, cuckold, bi mmf, oral, femdom]

“Come on out! It’ll be fine!”

Kevin took a deep breath. He and Sandra had been friends for years and it wasn’t as though he didn’t trust her. Still, there was a difference between trusting a friend and taking a step that he, himself, wasn’t sure he was ready for.

His chest was a little tight and that made it difficult to breathe. Only a little. It wasn’t as though the clothes he wore restricted him. They were snug. That’s all. Very snug. The blouse that showed off his shoulders had a neckline that cut across his obviously masculine chest yet, as he admired himself in the mirror, he adored how the floral pattern flowed down past his obliques. He wore a singlet under the blouse. It was black and provided a foundation that let the pattern shine, in addition to giving his body much more slender appeal.

The pair of tight, form-fitting jeans he wore made his hips and butt look good. As he admired himself in the body-length mirror in the store changing room, he considered that the trouble he got forcing them up past his thighs were definitely worth it.

After blowjob hookup with younger Bumble guy who made me lose myself during sex [FM]

So I’ve posted about Mike, the guy I was hooking up with/dating for a bit last year. [Here](https://www.reddit.com/r/gonewildstories/comments/bke4zl/my_first_time_with_a_guy_from_bumble_fm/) is the first story, with all the details about how he made me do things I either really never did before or would never do with someone who wasn’t a long term boyfriend. [Here](https://www.reddit.com/r/gonewildstories/comments/bq2knw/my_first_public_blowjob_fm/) is the second story about how he made me cum in a stairwell at a fancy rooftop hotel bar and then came on my stomach after I gave him head. Again, I never did anything *near* that risque in public before, or since.

More than a few people have asked for pictures. I wouldn’t share any of his without his permission. [This](https://i.imgur.com/fiH1OZm.jpg) is the best you’re going to get of me unless someone can tell me a better way to blur my face rather than blurring half the picture. But at least you have an idea about what I look like instead of just the descriptors in the first post.

Something more than sex [MF][Fsub]

”So…” Lucas moaned as Madeline swallowed his cock to the root. “Last time you mentioned that musical you wanted to see?” He moaned softly as she bopped up and down on his cock with trained familiarity. “I was thinking maybe- oh god yes, that’s the spot.” He moaned as her tongue found its way to the underside of his cockhead and broke his train of thought. “Keep going babe.”

Madeline worked her magic like she always did and Lucas’ breathing got more and more ragged before he came with a groan. Madeline’s lips stayed locked around the base of his cock as cum splashed down her throat. She slowly pulled off his cock and swallowed the last of his cum as she gave him a smile.

“What about it?” She asked relaxed as she undid her impromptu ponytail and let her hair fall freely again.

“I’ve-“ Lucas stopped himself to catch his breath for a few more minutes while Madeline checked her makeup in the mirror. “I’ve actually got 2 tickets for it, a friend of had to leave town and gave them to me.” Lucas claimed. “So I was thinking… maybe you wanted to-“

My hands smell of him [MF] [married]

My hands smell of him tonight…

He said goodnight, I said I wanted to stay up a bit more. He kissed me goodnight, like he always does, and I… I just couldn’t stop kissing him back. Normally I’d let him go, especially after he’s had a long day at work like today…

But not this time.

I kissed his lips, tongue, cheeks. His temples. That sweet nose, the chin… I got ticked by the beard. I love him like the first day. He is so tall, slim, sweet, smart and his eyes… When I first looked into his eyes, over a decade ago, time just stopped. I had never believed that stuff but back then, for a moment, I was lost. All I could think was “Oh”.

I still think that.

When he finally stood up from the couch, I stood up too, and kissed him some more. Then I let him go, and there I was, sad, just about to give up when I thought… I am gonna need me some more.

So I went after him, and blocked him in the corridor. He smiled at me, and I kissed him. I brushed my hands on his beautiful body, and then I don’t know… I had to have him.

We [MF] spent the afternoon together, with his permission. (w/pic)

Last week, my relationship with Sam and Aly (scroll past my dick pics for earlier posts with these two) progressed to a level hitherto unexplored by us: I was allowed to spend the afternoon alone with Aly, without any rules.

Well, there was one: Don’t get arrested.

Scroll way down for the sex. Also, this is Sam and Aly: u/fun_in_love

We’d hung out, all three of us, a number of times up until now. A couple of those just as friends grabbing drinks and appetizers. And Aly and I pushed the boundary a bit in the week leading up to this. We were well-behaved, mind you. Hard as that was.

“Above the clothes only,” she’d informed me. We had a couple coffee dates that week, each of us with our laptop and a whole lot of shit to do. It shouldn’t surprise you that sitting beside someone as beautiful as Aly for several hours distracted me from getting much done. But we were well-behaved. The first coffee-date, we only kissed and hugged upon my arriving. On the second, being so close to her was too much for me. I suggested we put the work away and take a walk around the neighborhood.