My [m] first time with an older woman [f]

I was on this random dating app, not even a particularly popular one and I matched with Jules she was 38 and I was 26 so this was definitely a bigger gap. At this stage in my life I wanted to experience an older woman, it was a sense of thrill.

Anyway Jules was stunning. Blonde hair, attractive, lovely blue eyes and had an amazing body, two kids later; impressive!

We got to chatting and it quickly became flirting, I knew Jules was attracted to me and could sense that she definitely wanted to let loose. She was in the process of being divorced but not officially. I remember asking her what she had been doing since she separated, was she making up for some lost time? Jules had been with a few people since her split but nothing really clicked. The conversation quickly turned naughty, Jules told me how she first squirted with a semi serious partner, she liked it but was adamant it required trust. We talked about her toys and what I might do to her… and what she enjoyed in the bedroom.

My opportunity was clear… I suggested gin and see where the night ends

[MF] She decided I was going to make her cum, but only on her terms.

This happened about twenty years ago but still burns bright in my memory after all this time. Sorry, I know it’s long but I wanted to set the scene properly.

It started, as with many things in those days with me trying to score some weed. My dealer, G was an alternative gay girl who was far too cool for her own good and a terrible convertor of straight girls. We taken a lot of drugs together and as a result were bloody good mates. As ever G had company when I arrived. No surprise, her house always had loads of random people lying around getting stoned. 

This is where I first saw Amy. I noticed her straight away the moment I walked in. Not just because she was stunning, she was, but more her aloof attitude. Sitting there on the sofa staring at the wall. When I said hello to her she completely blanked me. I mean fuck you too bitch. But there was something about her, something sultry, smouldering even. That said, I lacked any form of confidence back then so her being so fucking rude wasn’t very nice tbh.

[FM]18 The blowjob ghost

The blowjob Ghost is commonly found at Halloween parts and is recognizable by its collar around its neck with “The blowjob ghost” written on it, it’s white slutty clothing and further into the night often has white stains on its clothes usually around their chest or make-up that looks like it’s gotten wet. The blowjob ghost is trapped until it can give 10 complete blowjobs to different men in one night and a special supprise challenge once all 10 blowjobs are complete or it’s trapped until next Halloween. A blowjob ghost is also not allowed to say no to any guy who wants a blowjob and they can cum wherever they want

This was my idea for my Halloween costume and so far it’s worked great, I have an hour from when I’m writing this to give the last 2 blowjobs to avoid being stuck for another year

[TM] 42/30 Trans Man D/s Hot fuckin Weekend

I am a 42 year old, gay, transexual, man from a major city. For a while my life centered around pleasure based sex ed & I also taught kink classes. My service submissive is a 30 year old slutty trans faggot, darling bitch I met on an app when I posted an ad titled “Are you a good boy?” We chatted for a bit before meeting & I was overjoyed to learn that he’s particularly focused on service, protocol, chastity & giving head, as I love training for best service, including getting perfect head. Over a year later & things are better & hotter every day.

Things to know about us: we are both transexual gay men who are into the leather lifestyle. We have each had top surgery & still have our original bits down below, though enhanced by testosterone. We both happen to use the words “dick” &”hole” (hope you follow) to refer to our junk, & we both happen to be multi orgasmic; me much more than him, but as we mainly do chastity/denial/ruining with him, I don’t actually know how many times he can cum. Before this weekend, we’d topped him off around ten. I have given up divulging anything near the exact number of times I cum because most guys don’t believe me, as the average for someone with a penis is one. I now say “dozens & dozens” because that’s more digestible than saying “hundreds” or “After my first orgasm I will likely have continuous orgasms for the rest of the time we fuck.” The one thing about that is that I don’t typically feel done after orgasm, I just stop when I’m at a good stopping point.

[F] (30) [F30] I can’t help if but…

I’m a [30F] (30) mom if two. Single and obviously on the more thicker side. It seems like it’s what most guys like these days.
I keep getting messages daily or every other day of just random men I don’t know or met of all ages and color and size just sending me snaps of my social media of their junks.
Well, what I’m getting at is that is it bad that I actually enjoy when I get unsolicited dick snaps on social media. I low key really love it when I see that I can get someone that hard. It doesn’t matter who, black, white, old, young, I just enjoy them in general. Idk if I should be embarrassed about it

[FM] My (28M) friend (27F) cheated on her boyfriend with me

We got back to our hotel room extremely drunk after partying with a mutual friend that we were visiting in a different city. My [27F] friend’s bf wasnt able to join, but their relationship had been going downhill anyway. My friend was lying on her stomach on the bed and wanted to show me something on her phone, but held it so that the only way I could see it was to basically be next to or on top of her.

Some backstory: Our friendship had been platonic even though she’s often very flirty and suggestive whenever we go on trips – we always share a hotel room and share a bed most of the time. She’d come out of the shower either in a t shirt and underwear, or in just a towel (and ask me to “turn around” while she got dressed), ask me to help her with lotion, fix her hair, and a bunch of other things. I have no interest in her romantically although she is cute and extremely fuckable (I made a move on her once when she was single and we were both drunk and she rejected me lol)

Husband’s friend (30M) fucked pregnant me (28F) in car [FM]

After I regretted fucking my friend I denied doing him or any of my friends again. I told my husband (ben) if he wants me to get laid he should spare his friends and not ruin my friends. He agreed and told me to pick and make a move. He did not want to get involved.

I was supposed to visit doctor in my 6th week of pregnancy. My hubby had to go to work so he asked one of his friend to take me. He is single and kind of rich. I kind of had crush on him already. He picked me up in the morning. We were not that familiar with each other so we talked about casual things. I started dropping hints and light flirting. I didn’t expect tension to build up this soon.

At doctor’s the assistant assumed he is my husband and called him my husband’s name. We both blushed as he corrected her. He waited outside until I was done. When exiting the office I intentionally bent down right infront of him to fix my shoes. He was walking and bumped into me. I looked at him with a sly smile and continued to car.

Fucked in our friend’s driveway [MF]

Last Saturday we (F23) made plans to do some karaoke fun with a group my Fiancé (M31) has known for a few years. Somehow there was some miscommunication on where we were meant to meet them and ended up at the wrong house. Our friends live in a, for the most part, remote location and I found it too good of an opportunity to pass up. We drove halfway through their driveway when I politely asked my fiancé to fuck me. No one has ever pressed the breaks as fast as he did right then and there 😂 I have no idea if it was because there was a possibility someone was home, or the fact that half my body was out in the open while being fucked…but I came so hard (consecutively at some points) that it soaked through a spare blanket we kept for “emergencies”. It was the first time I had been fucked in a car so I plan on doing this again with him very soon 🙈

[FM] I provided some unforgettable fucking aid to a homeless man.

The background is that every day when I leave my apartment for work, I pass a homeless person sleeping on a covered bench. I talk to him every morning and occasionally offer him money. He has only lately been homeless, according to Covid, and I feel terrible for him. He is a genuinely decent man who, for the usual reason, lost his business to COVID and ended up on the streets.
After selling his company, he ran out of money to pay his rent. When he eventually revealed to me that he would soon be having a job interview at a nearby business, I was incredibly happy for him. I decided to let him come take a shower at my apartment before he left as I walked home from work after giving it some more thought during the day.
I got to him, handed him the bags, and after getting him some deodorant, toothpaste, a toothbrush, and other personal care items, invited him over. He was really appreciative of me because he hadn’t showered and the owner of the gym who usually let him shower there wouldn’t be back for a few days. We entered my flat after walking back there.
I let him take a shower and shave before we had dinner. He appeared to have altered when he was done. We talked about his life since leaving Covid during dinner, which only made me desire to offer assistance. My house was not very big. The bathtub was the only isolated area in the one-room apartment.
Despite the fact that I lacked a guest bedroom, I did have a couch, and I considered having him stay. I was still hesitant despite getting to know and trust him because of the horror stories you hear.
Story:
I took the dangerous step of allowing him to rest on my couch. Nothing occurred after that, and I felt totally at ease with him. The next morning, before going to the interview, he took another shower. When I returned to work, he was seated on a nearby bench outside my apartment. He approached me and hugged me. As I ushered him inside, he continued to thank me and told me all about how he got the job.
We sat on the couch after eating, and I brought him some wine. We talked while sipping a small glass of wine. As the time passed, he stood up and said, “I appreciate everything. Soon I’ll be able to live on my own. I informed him as he headed towards the door, “You can stay here if you want until you can pay rent in this area.
He shook his head, “No, I don’t want to intrude or anything. You’ve helped me enough, thank you. There shouldn’t be me there. I observed, “I don’t give a damn. It’s actually rather lovely to have a partner here. He shook his head in response. I pleaded with him to stay as I got to my feet and hugged him. I especially don’t want you to be there when you start work tomorrow. You can leave as soon as you can stand up.
He stated he would stay and thanked me once more. As we sat on the couch and watched a movie, I started to realize how much I cared about him. I also started to think he was quite beautiful. He was roughly six and two and thirty. He had a great body and was pretty tan. I asked him whether he had a wife. Since the time before Covid, he had never done so.
After I did, he quickly started talking openly about his relationships and sexual life. He answered, “I haven’t had sexual activity in nearly a year. Because of covid, I haven’t done anything and I’m lonely. Because of my COVID and the fact that no one with a normal life wants anything, I really didn’t want to be around any homeless people.
I waited a while before stating, “I want you,” drawing his shocked attention. I leaned closer to him and kissed him. Are you certain? He stopped me and inquired. I don’t think doing this is a good idea. I said, “I want this.” Do you want this? He paused for a moment before nodding and kissing me once again.
We sat close to each other for a minute and cuddled. I cautiously moved my fingers down to his trousers and felt his boner. He began to grope my breasts as I began to open the zip on the jeans I had purchased for him. As I took down his underwear, his dick jerked. I wasn’t disappointed, even though it wasn’t much. I stroked his bum before stooping to take him in my mouth. I leaned closer as he took his top off.
I slipped my tongue down his cock and opened my mouth to start sucking on him. He stopped me in less than a minute and stated, “I’m about to cum.” That’s okay, I said with a smile before starting over. He started cumping as soon as my hair touched his balls. As it exploded out of him and into his upper chest, he groaned. Massive ropes of come burst upon his chest, slowed down, and then began to emerge out his dick.
He twitched and hurt. I kissed him as soon as he began to unwind. I licked the come off his dick and then wiped it off his chest. I raised my head and grinned. That’s embarrassing, he said, and I grinned and responded, “It’s charming.”
I kissed him one more as I embraced him. I gave him a kiss, grinned a little, and mumbled, “I know it’s okay,” in response. After that, he said, “I can’t go tonight,” to which I replied, “Come snuggle with me.” He changed, and then we went to my bed. I fell asleep with him holding me.
I woke up the next morning to find my bed empty. He fell asleep on the couch, and I shook my head. While we were preparing breakfast, I brought it up. He waited before answering “Why didn’t you spend last night with me? I shouldn’t be in your bed because I’m homeless.”
I turned and cast him a quick glance. I don’t consider you in that way. You are a businessman who lost money as a result of an outside factor. Additionally, you are striving to stand up “He gave a quick nod to finish the conversation. He showered before leaving for his first day of work.

[FM] 23 I let my friend enjoy sucking my tits as he jerked away.

We ended up having a long, great night of drinking and then spent the early morning hours in my car. We somehow came to discuss his dick. I told him that after drinking, guys’ dicks turn pink, much way your hands and cheeks do. He insisted it wasn’t true. “Well, see, I know I’m right,” I said. Then, he removed his pants to show off his cock. He argued that it was unfair because he was tough, which is why it’s pink.
He started to stroke it right there in front of me. Watching his foreskin cross his cock’s pointed end made me incredibly horny. I gave him a brief glimpse by removing my tank top and coat and gently dropping the bra straps until my tiny tits were visible. He was reaching over and flicking my tight nipples.
He asked me to suck his cock. I told him about how great I am at sucking cock as he pulled me in and put my nipple in his mouth. I described to him how I first spit on it before allowing it to descend all the way into my throat till I start to puke. But because I wasn’t going to be swallowing his dick, I told him to keep touching himself.
He finally had had enough and had to get out of the car, still carrying his load.