Tag: Girlfriend

Fucking my college professor. [FM]

I posted on here a while ago and ended up deleting my account/posts because I suspected somebody had outed my professor, but turns out it was unrelated to my Reddit content. SO I’m back!

Back when I was 18 and a freshman at a major public university, I was taking a gen ed course (can’t say subject for privacy). My professor was insanely handsome (for writing purposes I’m just going to refer to him as Professor/my professor) and I crushed on him throughout the whole semester. Turns out that my thing for him wasn’t as discrete as I had hoped, because the day after the semester ended, I got an email from Professor. REALLY wanted to attach the email for y’all but I just looked back and alas, since it was to my university account from many semesters ago, it was automatically cleared away. Anyhow, in summary, this is what it said:

“Hey Student, I really enjoyed having you in class this past semester and I hope you enjoyed me as your professor. Tell me I’m not crazy and that you might be interested in me beyond just discussing (subject)?” Read more »

[MT] First time anal with my college girlfriend. :)

My last post was a bit too kinky for some of you, so I thought I’d do something a little more vanilla – one of the earlier times we tried anal.

So my college girlfriend was a transwoman, and you can read more about her in my previous posts – she was gorgeous, with small supple breasts, big doe eyes, and an average sized, slim cock (5 inches long, ~4 inches circumference). In my first gonewildstories post, I described our first sexual encounter, and in the second, a kinkier cum-saving adventure. What I’m about to describe happened somewhere in the middle.

So after our third or so 69-cum swap adventure, we were laying in bed, cuddling, and Meg asked if I had ever considered anal. I told her my experience was pretty light – I’d tried sliding a finger or two inside myself a few times in the shower, but nothing really routine or anything. She responded, “Oh! Wow. How did you like it?” And I very quickly realized at that moment that what she really wanted was for me to top her, not for her to top me. I told her I’d liked it, but I didn’t really have the flexibility to do it comfortably with my hands. She giggled and told me she’d actually never done anything anal before, and hadn’t even considered topping a man. I think at this point I looked pretty embarrassed, but she was encouraging about it. Read more »

I can’t tell this to anyone in my real life, but god, I loved it. [FM]

The only reason I’m posting here is because I need to talk to someone. Better yet, I need to tell someone what happened because I can never bring this up in real life.

It happened exactly 12 hours ago and I’m still thinking about it, still shaking all over. I can feel him again and again, I close my eyes and he’s there, his scent is all over me, his voice in my ear, his hands all over.

He’s tall and lean but muscular. He’s got the bluest eyes, teeth white as snow and dark hair. I’m petite, my hair goes down to my waist and my hazel eyes sometimes lock on his blue ones and I can’t look away. We want each other and we can’t be together. We can’t be together because he’s the adopted son of my biological father. The father I only met a year ago and since then, my adoptive brother and I have been falling for one another. Read more »

Cockring anecdote 1 [MF]

To start off, I’m K, my girlfriend is O. This happened when we were both 19 and had never used toys before.

So I bought myself a cockring as I was interested to see if it improved sex, O was up for it. We were round O’s mum’s house, things were getting crowded downstairs with other family members so we decided to go upstairs to O’s old bedroom.

One thing leads to another and the time to test the cockring was upon us.

Things were going great, she’s loving it, I’m bigger and harder than I’ve ever felt before so I’m loving it too. Then a knock at the door.
It’s O’s sister.
“O?”

O replies “yes?”, because what was she supposed to do? Say nothing, then the sister comes in, or say something, and the sister comes in.

The door handle squeaks, I pull out and jump into the nearest closet. I say into, it wasn’t open, I literally just rammed my body into a closed closet and pressed myself as hard into it as I could, trying to become 2 dimensional. Read more »

Another Saturday hookup [TM], [cheating], [cumshot]

First we finally decided to meet. After I found he had a girlfriend. The short black guy saw me about 10 feet away, eyes wide as saucers. And I didn’t see my next man so I kept walking. The boys down the block whistled at me as I walked by, a gang of four hustlers. I kept walking one of them asked me “comment ça va?” My next guy called me and we met up around the corner. We walked and talked and he out his arm around my waist as I availed it to him, and then we held hands and went upstairs to practice my French. Put his hand up my dress and lay across the sofa with my head in his lap. He played, and I spring erect and he grabbed my balls as I instructed, and I could hear his heart racing through his rib cage as I had the first if multiple orgasms. We then went to bed together and I rode and grinded my clitty on him. I then lubed up his cock and went down on him by rubbing his cock on my soft squishy nipple, cumming myself in the process. He told me to stop. Then I told him to finish on my tits. And he got on top of me and blew one of the biggest load I’ve seen since I’ve ever been apart of. It was nice and then I washed it all off in the shower and some dripped on the bathroom floor. Ahh, nothing like a good hookup. Dinner with her in the evening, desert with me at night. What have I gotten myself into? Swore I wouldn’t. Now here I am. We’ll probably end up seeing each other again, when his balls need that big ole milking again #diaryofatgirl ❤️❤️??

German town experience [mf]

So yesterday was a pretty awesome day. My girlfriend and I started dating about a month ago. We initially met up for a hookup to lose our v cards. We fell for each other and started dating. He haven’t had sex in awhile. I wanted to prove to her that I cared for her and not just the sex. Yesterday we went to a German town about 150 miles from our home town and we were having a good time. We eventually decided to have sex. But we couldn’t get a hotel so we decided to do it in my car.

We looked for a park where we could put up some window blockers and go to town. We eventually found a dead end that had condom wrappers all over the ground. So we blocked up the windows. I bought a cock ring to help her orgasm but the shit cut circulation off on my dick and caused my dick to turned purple so she used it as a vibrator. Read more »

The start of my comeback [M][FF] (Voyeurism, Gentle Femdom, Lesbian Sex, Exhibition, Breakfast)

This is the first part of the story about how I became the luckiest bastard in the world thanks to two of the most vivacious and carnal woman I’ve ever met. This story spans about a year and in that time I went from an awkward reclusive nerd to a confident somewhat charming nerd living with two wonderful partners. This part of the story contains some gentle female domination, voyeurism and lesbian sex that starts at the ***Sex starts here*** I wouldn’t blame you for skipping ahead. This next section is really long.

At the time my story begins I was a few years out of college and was completely lost about my life direction. I was working crappy retail jobs and just barely scraping a living while depression and mental health issues swallowed up my life until I felt utterly hopeless. On top of that I’ve never been a small person, I stand about 6’ 2” and am fairly heavy set which never really bothered me but years of eating my feelings and sitting around for long hours in front of a computer turned me from cuddly and lovable into just gross and fat. Read more »

Cabin for the weekend. [mff] [preg]

I and my girlfriend arrived at the cabin that we rented for the weekend. It was only a short distance away from the slopes we could use for skiing, and some local restaurants were also near by, which is what we told our parents we would be visiting.

My girlfriend’s friend was going to be coming over in about two hours, but my girlfriend could not wait that long. When we walked in the cabin we didn’t even look around at the rooms, she was already too horny. We found the couch in the living room and she started to undress, first taking her boots off and then her winter hat and scarf. I took my boots off and started on my coat, but at the same time, I watched her undress herself. She took her coat off to reveal her T-shirt and her blue-jeans were still on. Her breasts were hanging in her shirt, resting in her light fitting elastic bra. Read more »

Failed anal adventures with Ava [MF]

When I was in college I studied abroad in Asia.

It was an incredible experience, and I recommend it to everyone who has the opportunity. But my time there was made truly special by my first real girlfriend: Ava.

Ava was the language partner of a friend of mine. For those who don’t know, this means a local in your city who wants to learn your language, and you want to learn theirs, so you informally hang out together. I met her at dinner with friends, and we hit it off. She had long silky black hair, a perfect slender frame, nice curled lips, pretty brown eyes, and a cute butt. She was also a year older than me, at 21 (I’ve always liked older women). After a few more times hanging out with friends, I asked her to take a walk with me around our university at night, and I kissed her beneath the pines trees in the warm night air.

We became pretty inseparable after that, dating officially, spending large amounts of time together, and just generally basking in the happiness of young summer love.

One problem we had, however, was sex. Read more »

Meeting my neighbor [part 1] [mF] [cheating] [college]

As a freshly minted college junior, I finally had the chance to live off campus and really experience freedom. A few friends and I went in on a house in quaint New England town our little school called home. Within a few weeks of moving in, we turned a once decent family home into a complete bachelors pad. Posters were haphazardly tacked to the wall and beer cans adorned every corner. It was perfect. The hot New England summer was fading, and we decided to have a cookout to finally meet our neighbors, for fear of their itchy fingers dialing the police every time we had a party in the future–fear of underage drinking arrest is certainly real at that age.

We knocked on doors all around the neighborhood, and were met with smiles and non committal responses. Our next door neighbor wasn’t home, so we walked back into the house. It was getting to be late Thursday and our fake ids begged for a test drive at the local bars. As I came downstairs and waited to leave, I noticed the lights on in the house next door. My roommates were all getting dressed upstairs, so I hollered that I’d go invite our neighbors to our block party extravaganza. I let myself out the front door, walked the few yards down the sidewalk and rang the bell next door. Read more »