Girlfriend Archives — Page 290 of 1305 — NSFW story

My Girlfriend Joins in Blackmailing My Mother’s Best Friend

Please see Blackmailing My Mother’s Best Friend for background info. I showed my girlfriend Nicole the pictures of Paula cheating on her husband. I also told Nicole about how I blackmailed Paula. Nicole wasn’t upset as we had an open relationship. Nicole was about 30 years old, average height/body type, and has red hair. Nicole was also bisexual and was sexually interested in an older woman like Paula. I told Nicole we can make that happen. Nicole and I went to Paula’s house. Paula was wearing a purple dress. Nicole was wearing an orange button shirt with jeans. I was wearing a sweater with jeans.

Paula was wondering why I was at her house with Nicole. Paula and Nicole didn’t know each other that well. I told Paula “You will soon find out.” Nicole kissed Paula. Paula initially protested and said she was not a lesbian. I countered with remember our deal. Paula agreed to go along with it. Nicole resumed kissing Paula. Paula began to enjoy it. They were kissing each other for 15-20 minutes. All 3 of us went inside Paula’s bedroom. Nicole removed Paula’s dress and bra. Nicole and Paula laid down on the bed. Nicole began touching and sucking Paula’s breasts. Paula liked the soft touch of a woman. Read more »

[M] How I had sex with my girlfriend…

HI, yesterday, I had sex with my girlfriend. She came to my place. As my parents live somewhere else and my aunt had gone somewhere, it was just me and her. she came in the afternoon. We talked for sometime and then we had sex, in the evening, we went out for sometime. We ate together, roamed around, here and there for a while. Then, we had sex in my car when we reached home. After having sex in the car, we went inside the house and had sex again, It was awesome. Then, we slept naked and she left for her home today, in the morning. She also lives alone as her parents live in Ohio.

My Catholic Ex-Girlfriend’s Journey to the Poophole Loophole – Part 1 [MF]

Sorry for Repost. I accidentally deleted it, I think. No need to upvote 😂.

Spring of 2008.

Melissa and I met at Freshman orientation. We started dating in the second semester of my sophomore year—my first official college girlfriend. We had both just started dating. I got to our school on athletic scholarship (baseball), and she got in on her academic acumen.

The baseball season had just started, and Melissa was determined to make all my games, even though I told her she totally didn’t have to. I played center field, and I was pretty decent. But I really got a boost to my batting average when Melissa and I dated.

Melissa was very cute. She had a shoulder length brown hair, and stayed in great shape. She was about 5’2 and had a nice butt. Perhaps the best physical feature though were her impossibly large boobs. She’s had a reduction now, but man, they were huge.

Melissa was raised very conservative. Most religious girl I ever dated. She attended mass every week. She didn’t drink and she never used profanity. She had a few boyfriends in high school and one her Freshman year but, she—unlike me—had never done anything with them besides hold hands and kiss; she was a virgin. She wanted to save herself for marriage. Read more »

My Ex-Girlfriend’s Journey to the Poophole Loophole – Part 3 [MF]

I remember looking in the stands after I hit that home run, my sexually repressed girlfriend jumping up and down. Absolutely gorgeous. Just looking at her made my dick twitch a little in my pants as I thought of the blowjob she had just given me in the parking lot.

She waved at me and I returned the gesture. I’m pretty sure I saw her eyes go to my groin, but I couldn’t be sure since she was so far away. As I headed into the dugout to wait for the end of the inning, I began to think more about what had happened before the game. You see, contrary to Melissa’s strict Catholic upbringing, she had previously given me a handjob, let me fuck her gigantic tits, and just before the game she had given me a blowjob to completion.

Melissa told me later that she had masturbated for the first time in the car after I left, and she even gave herself her first orgasm. She had always been told that it was a sin, but that her desire was just too strong. Read more »

[MF]My ex liked to humiliate me, and I like that

Has had a cuckold fetish for several years. I was a virgin until I was 20 and then I met my first girlfriend. I met her at a friend’s party, and shortly after I left her, she was kissing one of the party people (he told me about it some time later). I was seeing her for a month. We had sex exactly twice. The first time she was willing, but the second time I took her for pity because she said all the time that she was tired, sleepy or that she didn’t feel like it. She had an ex that she loved to tell me about and they continued to be friends. From the very beginning, she told me how good he was. She talked about how she gave him a blowjob more than once, and even asked if she could do him, she also said that he used to cum inside her a regular basis and generally had sex without condoms. On each of those two occasions, I had to put a condom on and eat her pussy, and any pleas for a blowjob ended up refusing with a nasty smile. I didn’t earn much when I was with her because I was in school, but she didn’t mind asking me to buy things for her, which of course I did. Her ex was unemployed and she paid for their things and had a job during her relationship with me. Read more »

Julia, Aged Like Fine Wine. [M/F] [MILF]

*Note: I originally posted this story two days ago, but was unhappy with that version. After some constructive feedback from a fellow author, I decided to revise and expand it a little. Enjoy.*

The woman lived on the other end of the block from me and she was a fixture of the neighborhood. In the few months since I’d moved there, I saw her almost daily (usually as she worked in the yard or power-walked around the area), but up to that point, I’d yet to talk to her a single time. She was in her mid-forties with shoulder-length hair, tanned skin, large breasts, and had what looked to be a very fit figure. Considering I was a healthy, twenty-five-year-old man, the fact of the woman’s attractiveness was not lost on me, but because I tended to be more interested in women my age and younger, I never thought of her as an option, romantically or otherwise. She was just the nice-looking, older woman from down the street; no more and no less, but that was all about to change. Read more »

Wife’s past remembered [MF]

On a recent trip I had with my wife it was revealed to me more of her hot encounters she has had with guys when she was still in high school. Most of what I had shared about her so far was was during her college years with the exception of when she was a babysitter during her early high school years.

She had shared to me that she used to give this one particular friend of hers a blowjob whenever he wanted in high school. I believe the timeline of this was right after her encounter with the adult dad as a babysitter. This friends of hers was one of the popular kids who was known for getting away with things. Read more »

A pleasant chat [Mast][Solo][FF]

*Ding!*

My phone notified me about a new message. It’s was late, I was just about to fall asleep. But now I was curius about the message. Who could it be at this hour?

I reached for my phone and unlocked the screen. There was a notification from Messenger on the screen. Someone called Caroline had sendt me a message.
I didn’t know any Caroline, i thought it probably was one of those sex scammers. But I opened the message anyway.

*Hi! You don’t know me, but we’ve met once.*

That was all it said.

I looked at Carolines profile picture, and got a vague feeling that I recognized this person. But I couldn’t tell from where. Strange.

I answered her.

*Hi, who are you?*

I waited.

10 seconds… 12 seconds… 25 seconds…

*Ding!* – a new message.

C: *Thank you for answering me 😊 I think we met once this summer.*

My head was completely empty. Where had I met this girl?

Me: *This summer? When? And who are you?*

C: *Ok, this may sound wierd, but do the word ***shower*** jolt your memory?* Read more »

My [29M] hot friend [28F] in my bed

We just came back from a weekend trip. I booked a hotel for us, two beds. We’re friends, nothing more, going out for a vacation. We spend a lot of alone time together and we get along really well. I had other women to invite, but it was her company I wanted. When we came back to my place, she didn’t have a way to get back home, so I invited her to stay here with me for the night, in my bed, no expectations.

I remember when I first met her, it was at Coachella. My girlfriend at the time met her and we all hit it off. I remember vividly, she wore a matching pink skirt and top, and she was the wildest person I had ever met. She was so full of energy, cute, sexy, tatted, and she was fun to be with. She had this innocent sexy vibe to her, and I liked being around her.

We all kept in touch after that Coachella, seeing each other and partying often. But me, being the faithful person that I am, never made a move, never let her know that how interested in her I was. Read more »