Sex and the boss [mm]

I’m a 27 year old male (the receiver) my bf is 51 (the giver) But before I got with him, I slept with his dad!

His dad (now 72) , was at the time the manager of where my sister and grandma worked. He came out as gay in the early 00’s. He was a nice bloke and always got invited to family gatherings & parties. When I was 16 and thinking about coming out, I spoke to him – he was super cool and told me how to do it, where to seek support and what to expect from people.

When I was I signed up to the Grindr app for Gay hook ups. After about 6 weeks, a message popped up and it turns out to the dad. We got chatting and exchanged a few pictures etc, in the end I went to his – we had a few beers and I gave him a BJ and went home. After a few more meets I finally agreed to let him fuck me. Lots of lube, condom’s and a strict understanding that when I said it, he would pull out. This worked out well for a few times.

[M]y first [M]ale on male experience

So I’ve set up this account as there will hopefully be more to tell in the next few weeks. If this is ok with everyone and they enjoy it I’ll be happy to post further chapters!

So a little background (I’ll insert a sex starts here! For the people that want the smut). I live in the UK and am 28 years old. I’ve known I was Bisexual since I was 17 but I’ve had a girlfriend for the last ten years. I was completely open with her and told her when we first met that I was bisexual. However I’ve never admitted this to anybody else.

This time last year we split up. It was amicable and I never cheated on her but I’d be lying if I said I’d never watched porn and even messaged some people. I think she cheated on me but it’s kind of irrelevant. We both knew we were done.

For the longest time I wanted to be alone, but after so long I started to have needs. I downloaded a popular app for gay dating and decided to speak to some people and see where it goes.

[m]y uncle let [m]e give him a bj

(Everyone involved is 18l)So ive posted before about how a really close family friend who I consider an uncle was suddenly hot and in my fantasies, well today it happened the story follows like this

So today the U came over,lets call him Bocaj, we were home alone amd talking about me coming out as gay a few months prior, he asked me some leading questions like if I was into anyone (you duh) stuff like that, we stopped talking and he went to play his phone, I suddenly hear a loud moan and look at him watching porn. We both were fully aware and he looked at me as I looked at his phone and him in disbelief, I look down and notice him kind of twitching. As if instinctively I crept my hand closer and closer both of us quiet. I finally had my hand on his other thigh. To not me graphic I gave him a bj and he is going to rearrange my guts tomorrow

Tl:Dr; look at the title

My [M] one and only massage by a [M], unexpected. (Really happened, a bit long)

I was just over 30 at the time, unattached and often went to different massage places. This was way back before the State of Oregon decided to legislate the massage profession, so it wasn’t really that difficult to find a woman willing to do a happy ending. In fact, most places had a receptionist out front that told you the rates and how much it was with a “hand finish.”

That actually was nice, a single guy could get the edge off without having to go through all of the wine and dine stuff. There was one place in south Portland I really preferred, it was clean, they had showers, and the price was right so if a guy struck out on an evening’s hunt for a one nighter, stopping off on the way home was a sure thing. I was young and in shape, had a few bucks in my pocket so usually I could find a friend in one of the clubs, but this night I was having no luck at all, so around 2 in the morning I drove down. The place was always open, I never saw it ever closed. Those of you that knew Portland back then will know about it, it was named after the creek nearby, same as the road it was on. The first thing I noticed was the parking lot in the back was full, I had to park down the street. I knew they usually had 3 or 4 girls on staff so it shouldn’t be a problem waiting, a few times before I had a short wait.

First time with another man [MM]

In my early 20s I went through a devastating breakup. My girlfriend of several years admitted to fucking one of my friends. I went into a depression and filled the void with porn and eventually, random sex. I got really into TS and gay porn on top of my regular stuff. I found myself browsing craigslist personals in search of my first gay or trans encounter. Trans was a lot harder to find in my area. This was the days before grindr and I didn’t like the exposure of a dating site.

I found a guy looking for mutual fun in an adjacent city, roughly a 90 minute drive. He was my age and moderately fit. White with brown hair and hazel eyes. Not weird looking, and I really didn’t have a gauge for attractiveness in men. Not feminine at all, which might have helped later, but I didn’t have a lot of options. Most of the guys on craigslist were way older, overweight, and extremely hairy. That’s a hard sell for a guy who’s only been with women.

I’m a straightish guy but I love botto[M]ing for transwomen, and occasionally men.

I’d consider myself straight. I have a girlfriend who I love dearly and have never cheated on. Before we met thoug, I spent years sleeping around. I went through a rough breakup and started watching a lot of porn. Eventually transgender and gay porn. I started fantasizing about tasting cock. At the time, craigslist still had personals and escort pages. I found myself browsing them and masturbating to the ads. Eventually I got up the nerve to try a TS escort. I’d already been with several female escorts so that part didn’t really bother me. I met this trans escort at her apartment. She was a gorgeous athletic latina with a fat cock. I was nervous so she sucked me for a while before I got up the nerve to suck her. I’d had one gay experience before so this wasn’t the first cock is sucked. Afterwards I topped her. I came so hard in her ass and felt so dirty after.

That time I [F] role played a gay male fantasy with my ex [M] over text

Context:

I [F23] and my ex [M24] have been broken up for about a year. We live in different cities now, but recently we’ve been trying to reconnect a via text. Just friendship, though. As context, you should know that although my ex is straight, I always thought it would be really hot to watch him with another guy, and I told him so back when we were dating. Sometimes he would tease like he was interested, but in the end he always came back to “Just kidding. Not interested. I’m straight, after all.” So, nothing ever happened.

But…..last night, I the topic came up again. I mentioned him how hot it would have been for me if he had ever let a guy take him home. And then, he shocked me: he said it would have been hot for him too. And he added, “Seriously. I’m not kidding this time.” I was shocked…and more than a little turned on. Shortly after that the conversation accelerated into less of a discussion and more of a co-created fantasy, imagining what might have been, what…well…what could still be, I guess:

Our First Session [Gay] [MM] [Blowjob] [Massage]

I arrive at your door and you let me in. We discuss any boundaries you have for this first session, and you tell me I’m ok to do whatever I want to do to you with my hands and mouth, but nothing else. I let you know that I have the same boundaries, but as discussed previously, there’s no need for you to reciprocate. I also reiterate that if you change your mind at any point, say the word and we’ll adjust or stop.

I can see that you’re nervous, I am too. I ask if you need a few minutes to chat prior to beginning, and you shake your head, and motion for me to follow you. You lead me to your bedroom, disrobe and ask how I want you. I tell you that we’ll start with you face down. I ask how you want me, and you say I’m fine as I am. I nod and you lay down on your bed, facing away from me.

The Camgirl Part XI: Chocolate Insomnia [mostly fluff and plot] [lots of unresolved sexual tension]

**XI: Blake and Liam**

**Blake**

Sleep, it turned out, did not want Blake as much as she wanted it. Not tonight.

Her mind just wouldn’t quiet. Even curled up next to Chloe as she was, feeling safe and warm beneath the blankets in her friend’s embrace, the knot in her stomach hadn’t left completely. It certainly hadn’t helped that she’d been able to hear Liam and Marie going at it when she and Chloe got back. Blake’s friend, wonderful as always, had rushed them into her room and given her a hug and a kiss. Blake had almost been weak enough to kiss her back. It wouldn’t have been a big deal, not normally. She and Chloe still made out occasionally, usually when alcohol was involved, or to fuck with boys, but they never let it get emotional, and Blake was still far too emotional for that right now.

With a muffled huff, she carefully extracted herself from the blankets and Chloe’s arms, making sure not to wake her friend.

I need chocolate. Chocolate and sleepy-time tea.

[M] Just had my first sexual encounter with another man.

Let me start off by saying I had a feeling this would happen some day because I’ve always been a little curious.

My friends from work invited me out to a gay bar last night. (Because who doesn’t love working hungover on a Monday.) I obliged and after dancing and having a surprisingly great time as I was up at the bar waiting to order more drinks a man offered to buy me one, I was cool with it and we ended up conversing for a little while, he asked me the question (so are you into men) which I knew he was going to pop sooner or later. I said no but before I could even think, the tequila I’ve been having all night had me blurt out “But that doesn’t mean I don’t appreciate others with a big dick.” I’m quite sure that drunken statement made me whole evening take a left turn. His eyes lit up like it was Christmas morning. Not even 10 seconds later he asked if I had any photos, I did and wasn’t immediately comfortable showing him, and I told him that so he said the infamous line “I’ll show you mine if you show me yours first.” It worked. It was now around 10pm and I went and told my friends I was going home so I wasn’t in too bad of shape for work the next morning. In reality I ended up taking an Uber back to the mans apartment after he offered drinks and pizza, which happened to only be a few blocks from my own. For the sake of keeping this story as clean as possible I will end it there, but for those who stuck around to read all of this just know I called out of work the next day and can safely say I survived a 9 inch penis. 10/10 would probably do it again. Cheers!