Tag: Girlfriend

Free Use Town 4 (34M/23F/18F) [Freeuse][Cheating]

This is weird. Normally, I’m not as lucky with the ladies. Not like Lenny and Kyle anyway. I’m neither tall nor short, about 5’7, but I have the typical prison body and I kept it. I have a lot of tattoos on me, and my hair is short with the sides shaved. So, on the outside, I look like a thug. But I own my business, I work with my workers, and I get along with them really well. Whenever I work with them, lunch is on me, and I’d like for say I’m well liked.

Before me and the guys separated, the first time, I stayed back a bit to talk with the old man. While everyone else is fine with what he said, I was a bit more skeptical about it.

“What can I say to make you feel more comfortable?” He asked.

“Well, for starters, why the decline? What lead up to it.”

He gave a disappointed sigh. Not to me, but I think for the situation. Read more »

[MFM] Older guy makes my girlfriend cum and swallow his cum.

A couple of years ago, I met my girlfriend at the time on a foreign trip. From the very first night we engaged in raw sex, so it was immediately clear to me that this was going to be a fun relationship. Upon returning to our country, we decided to be together. Since she lived in another city where she attended college, I came every few weeks to spend a few days together. We spent those few days mostly having sex and trying all the possible things we could think of. Over time, we realized that this relationship was based mainly on sex, but that was okay with us at the time and we enjoyed it to the maximum. Read more »

[FM] Open Relationship Experiment (Part 3)

This happened to [m]e last summer before pandemic somewhere in Nothern Germany. Excuse any misspellings, English is not my native language.

Make sure to read Part 1 & 2 first.

—-

For a while we lie side by side, her head on my chest, without saying anything. My thoughts are circling. I was strangely satisfied and confused. Just a moment ago my wife was sucking my balls through my cock and only a few hours earlier she had her first sex date with her colleague Kevin. I couldn’t get one thought out of my head. Was it really the first time?

“You’ve had sex with him before, haven’t you?” I asked her directly.

“What?” she had already understood me.

“Have you had sex with him before tonight? You can tell me,” I repeated.

“Yes. But it’s not what you think. It was really just sex,” she replied after a long pause like a dog who knows he’s made a mistake.

“How many more times?” I wanted to know.

“I don’t know, maybe 10 times”.

WHAT?? 10 TIMES AND I DIDN’T GET ANYTHING?” it screams inside me. Read more »

Dawn Aced the Oral Exam [MF]

I had seen Dawn around campus. We were in a class together, but never talked. That is, until she saw the book I was carrying.

“You’re taking that test too? There’s so much stuff. You interested in studying together?”

I tried not to notice that her burgundy shorts were riding up her muscular pale thighs. Or that her nipples were clearly visible through her t-shirt. Or that the breasts her nipples were attached to were either 36B or Cs.

“Definitely. Here’s my number. Give me a call when you have time and we’ll make it happen.”

It didn’t take long. She called that evening.

“Is tonight good?”

It was. In fact I was studying either way. I suggested we meet in the library. Dawn had a different idea. She said she was coming to my room.

When she arrived, she was wearing a black dress with white polka dots. She looked beautiful. The only hint of those beautiful legs was via a slit up the side.

Turns out, Dawn was very bold. She walked in and sat on the bed. Read more »

Fun in a classroo[M]

A few weeks ago my girlfriend texted me and asked if I could hangout because she had some news to tell me. I said I’d love to, but she has to tell me while I fuck her from behind and she agreed. I went to her school and waited for her message me when I could come to her classroom.

I walked in, we both sat down by her desk and away from the door and I started to kiss her neck while she was talking to me. We began having a conversation while I was teasing her and getting her ready for me. I made my way down to her tits and I bit them, sucked them, and moved my tongue up and down on them, only stopping to give my responses to our conversation. After a couple of minutes, she took my head and kissed me and said “fuck me.” Read more »

Crossdressing Flight Attendant [m21m55] [m21f22] [crossdressing] [oral] [foot massage] [pantyhose] [uniform]

I’m not a girl.
My name is Eric Redman and I’m 100% a guy through and through, which is why you might be surprised to learn that no one knows that. 
Have you ever seen those super androgynous people where you just can’t peg down what their true gender is? That’s me, and it’s been me my whole life. I’ve been mistaken for a girl so many times I can’t even keep count. Teachers, classmates, coworkers… one time a doctor even called me ‘she’ when I was getting some antibiotics even though my paperwork clearly said ‘male’. 
My parents were horrified at my gender ambiguousness, so much so that they tried everything to ‘right’ it, including buzzed hair, baggy clothing and all the contact sports they could fit me in. They even had my hormone levels checked out, which all turned out to be in order. 
When puberty finally came around handing out deep voices and muscles, it seemed to just pass me by. I grew for sure, but not much. I looked just as ambiguous as before. One thing it did gift me though was an insatiable sexual appetite that just wouldn’t leave me alone. There was hardly a day that passed by without at least one jerk-off session being performed. And the real kicker? I usually did it wearing my mom’s clothes. 
You see, I had developed a real interest in cross-dressing during my teenage years, partly because I could pull it off so well, but also because it turned me on so much. I thought I was Trans for a time, but no. This was definitely not a wrong body thing as I liked being a guy. I just… liked being a guy who pretended to be a girl more. 
My parents never knew. Seriously. They legitimately never found out that I would sneak into my mom’s drawers, put on her pantyhose and heels and masturbate like a madman. 
At 19 I moved out and never looked back. Now when I say that, I really do mean I never looked back; I’m 21 now and haven’t spoken to my parents in over two years. Or my friends, or anyone else I ever knew.
I started a whole new life in which everything about me was a lie. And you know what? I fucking love it.  Read more »

[FM] Found a great new way to make my married girlfriend cum

This is about [this girl] (https://www.reddit.com/r/Cuckold/comments/p5vgow/i_wasnt_expecting_this_from_tinder_but_i_guess_im/), who I’ve been seeing for a year now. We’re both in open relationships.

As I discussed in the other post, she really loves it when I give her a big load of cum. Recently, after I came in her pussy, she told me to stay inside and keep fucking her. So I kept fucking her, in missionary, with my big load of cum inside of her. I was wearing a condom so I didn’t want to fuck her really hard – I concentrated on grinding against her clit. She loves this, so she got worked up very quickly – and that kept me hard, even though I just came. After a couple of minutes of grinding she had an intense orgasm – but why stop there? I just kept gently fucking her while she kept grinding into me, with my big load of cum inside her, and she had about 4 more orgasms. The dirty talk helped too. Now we do this every time.

She says: Read more »

[M] 24 girlfriend cheating with personal trainer

Just wanted to share since this is on my mind and get someones perspective female or male who is open minded. I found some pics on her phone that Obviously made it seem like she was cheating. Me and my girlfriend has been dating for quite some time now. She recently cheated which I found embarrassing and hot but as I found out more and had more time I thought it was pretty hot. It happened a few months ago and I kind of indirectly helped. Obviously as more time goes on I’m more understanding to why she did it. This happened a while ago but it’s been extremely wild and honestly to be fair there were tons of red flags. I should have seen or had an idea it was happening. I do have mixed emotions about it if im being honest. Like I said overall complicated situation

Watching My Wife Fuck Her New Girlfriend [MFF]

I made pancakes for breakfast. Anne, my wife, had spent the night sleeping in her new girlfriend’s bed. Maxine had been insecure in her sexuality. Anne had helped her decide, Maxine was definitely gay. After one night with Maxine Anne had spent a few hours with me, then spent the next night fucking Maxine.

Maxine was radiant when she got out of bed. Her experience with Anne had been a revelation to her. She was almost giddy with joy. Anne was a bit slower out of bed, she was never a morning person.

Pancakes and orange juice later we went into the city. We were staying at Maxine’s family’s apartment in Rome. Yesterday we’d explored the city but today we were little slower. We found a Cafe and sipped coffee for a long time. Then we moved on and found another Cafe to sit at.

“I’m gay.” Maxine said. She said it few times in the last couple of days. I looked at her quizzically. She smiled at me. “I’m gay and I’d love to spend more time with Anne. But I’m starting to feel a little guilty about taking up all her time. Can I have one more night?” I smiled. Read more »

My [M] girlfriend and her ex

My girlfriend and I are in a semi-open long-distance relationship. That’s to say, anything and everything other than sex is on the table, while sex, defined as penetration, is off it. We have both been happy with this arrangement. That is, until she started hanging out with her ex again.

Since then, we have both been happier. I am kidding. I think we have both been kinkier. I get an unexplained boner when she tells me that they’re going for dinner and she knows this. I wonder what their chemistry must be like, what his eyes must be looking at, and whether he misses her undressed as a longing or as regret. It all turns me on. She teases me with the details. I cum every time.

She sends me a selfie before she leaves. She sneaks one in when she’s there. I am updated. My mind is at peace. She sends one when she’s back. I look for signs. Is there is a mark around her neckline that wasn’t there before? Is her lipstick slightly smudged by someone else’s lips, or did she just wipe off that breadcrumb? I zoom in with one hand. I anticipate and dread with another, hard. She tells me they limit themselves to a hug. Do they? Do I want them to? I think so. She thinks so. He thinks so. I don’t think so. I have zoomed into tens of selfies. No sign. I tell her there’s no sign. She asks me to look closer. She laughs. I don’t want to see a sign. But I want to look for it, in anticipation. Read more »