[TF/TG] From Boyfriend to BFF

Requested by reportahri on DeviantArt

“Max are you even listening to me? I asked you what you think of this one.”

Max looked up from his phone to find his girlfriend, Lisa, glaring at him in yet another yoga outfit. They’d been at the mall for hours as she tired on various leggings and crop tops, always asking for his opinion when they all just looked the same. What did it matter if one pair had a little flower in the corner or a slightly different pattern?

“It’s great. You look hot babe.” He offered and Lisa just rolled her eyes.

“That’s what you always say. Do you even remember what the last thing I tried on looked like?”

Nope. It had left his mind the second she’d gone back into the changing room but something told him saying that wasn’t going to end well for him. He tried a different approach.

“It’s just, you look great in everything!” He smiled, “They’re all my favourite, I can’t pick.”

Rather than being flattered Lisa groaned in frustration and Max felt his temper flare. It was her idea to drag him from shop to shop looking at outfits when she knew he hated it.

Retail Wet Dream [M18/F21/F24]

Middle and high school were rough for me. It’s not that I was bullied, I had friends. It’s not that I had bad grades, I did fine. It’s that I always had a feeling I wasn’t presenting on the outside who I felt I was inside. I was always a little overweight and never found a way of getting myself in shape to feel more confident. And I could never believe that a girl would find me attractive, truly.

Instead of going to college like everyone else in my uppity suburb, I took time off. I thought a big risk would help shake me out of my complacency and malaise. My parents were very skeptical, but because I promised I’d go eventually, they didn’t fight me too hard on it.

My close friend became my girlfriend [FF]

I have been friends with Julie for about a year and a half. We spend a lot of time together. I was always physically attracted to her. We have cuddled, kissed a little on occasion, then eventually had sex.

We had sex together regularly for about a month….
Saturday morning after a wonderful night together and falling asleep naked wrapped around each other I felt her hands caressing my body…

She began softly kissing me with her beautiful full lips. Her tongue lightly dancing with mine. My nipples were hard and my pussy was wet. She caressed my face and looked into my eyes and said, “I love you”. A tear came to my eye and I said, “I love you too”. Then we continued to kiss and caressed each other’s bodies.

She started to rub my pussy, as I moaned and gasped at her touch. I reached down and lightly slid my finger up and down her wet slit. She whispered my name as I rubbed her clit. I kissed my way down from her neck to her breasts down her stomach and finally her pussy.

My gf, Amy, tells her friends and me about her hot past (FFFM 21)

This is continued from a story about my birthday at my gf Amy’s vacation house.

My gf, Amy, was sucking my dick on the side of her pool and telling me about how she sucked off two lifeguards back when she was a lifeguard.

Josie said, “Damn, Amy, I did not expect this from you.”

Amy said, “Josie, I invited my boyfriend’s ex girlfriend, you, to my house for group sex with me. What makes you think I wouldn’t suck two dicks at once.”

Josie said, “Fair enough.”

Amy was still sucking my dick and then paused. She said, “Jack, sorry to drop that on you for the first time in front of the girls. I just got horny and it slipped out.”

I said, “Uh, Amy, I’m kind of surprised by this, but I want to hear more about this story.”

Amy smiled at me and licked my dick.

Amy said, “you know I dated my first boyfriend for a little more than a year. He was my first. I never told you why we broke up.” She bobbed her head up and down on my dick a few times and then said, “Are you sure you want to hear about this? Me with other dudes?” She was licking the head of my dick and looking up at me. “You might find this story kind of…slutty…very slutty,” Amy said.

Fucking a work colleague in every hospitality box on the top floor of a Premier League football stadium [MF]

I have been a long time reader of this thread but never felt comfortable with the username Reddit created when I started. I joined Reddit under an anonymous name while I was bored in my previous relationship but never really felt comfortable with the name. I posted one story under my previous username that I will one day repost but this month’s monthly submission contest winner felt like a great place to start writing up my sexual history with the world.

This story happened when I was 20, so about 12 years ago. As the title says, my first-ever job was at a football stadium. I won’t disclose the location or the club for obvious reasons.

I’ve included some ****** below so you know when the good and really good stuff begins.

I started the job when I turned 17. I was keen to get out and work as I had passed my driving test and I knew working would mean I would meet new people. I started as a waiter in the main VIP hospitality sweet. I was your typical 17-year-old who wouldn’t say boo to a goose. The management quickly saw I was shy and moved me to carry drinks to increase my confidence and to start interacting with customers.

I made out with my girlfriend’s sister [M/F, Fiction]

I recently graduated from Michigan State University. My girlfriend hooked me up with a position in her mom’s company. My first day at work went pretty well until end of day when we closed down the office. My babe was supposed to pick me up after work but she left me waiting for an hour without texting me back. I was think about what could go wrong. Anyway, I decided to wait for a little longer in my cubicle. That is when a cute brunette girl walked in to my office. She introduced herself as Abella, my girlfriend’s sister. My girlfriend rarely talked about her and honestly this chick is hot as fuck. After some small talks, she let me know that every new employee was left alone like myself because this is a test. I laughed and asked her what kind of test this was..anyway, she showed me around her mom’s company and in the end, we ended up in her mom’s office. She locked the door behind me and let me know that she found me attractive and in fact she has been single for a long time. Things got a little weird since we were the only two people left in the room. I couldn’t stop having some naughty thoughts about Abella in my mind since she is hot but I was acting cool the whole time. But then Abella slipped and felt into my arm. That’s when I could not contain myself anymore and decided to go for a kiss. Holy shit! She didn’t stop me there. She actually told me that she was waiting for me to make a move….

20 [M4F] Savannah,Ga if you truly believe age is just a number this one is for you💝

I am a 20yo male and I have always found it interesting having conversations with older women like some of my college staff members. While growing up over the years some of my friends parents (Milfs that were married) would always tell me that I would have intriguing conversations when I would tell them about what I wanted for myself in the future & about being finically stable then compare me to the way their partner talked. Sitting there having those conversations would be a turn on for me when I saw their beautiful smile and small giggles 🤭 and I could tell they would look me up and down just seeing my D*** print from my basketball shorts or at more professional events when I would dress differently getting complements on my cologne with a unique button down with some slim khaki pants.

Dating an Actress Pt. 2: The Instrument [M/F]

(All characters are 18 or over and any past sexual encounters described also occurred when they were 18 or over.)

So after the last rehearsal I was like 99% sure Ainsley Park wanted to fuck me. On the one hand, Ainsley was hot as fuck. And my girlfriend Delilah was taking load after load of cum from several of her cast mates. But on the other hand, Delilah had a pretty rigorous code of ethics and all of her what-looked-like-infidelities were to her just expressions of her character in Cabaret. That little alt right shithead Ben Stevens tried to fuck her and she turned him down saying “Sally Bowles does not fuck Nazis.” And sure enough there’s no implication in Cabaret of any sexual connection between Delilah’s character Sally and Ben’s character Ernst. She didn’t fuck Chase Park, one of the most popular guys in school, because he was playing an old man who Sally wouldn’t be interested in. To her it was SALLY doing all this fucking. DELILAH was 100% faithful to her boyfriend. I had trouble wrapping my head around this since Sally was a fictional character and her vagina was very much Delilah’s. But that didn’t change the fact that if I fucked Ainsley it would be cheating. I didn’t have any of Delilah’s “artistic” justifications.

[MF] [Str8] Lazy Afternoon in a Hammock, Part II.

*Check out Part I of this story first (in the comments)!*

I set up near trees near the busy intersection of several paved walking paths. I had a perfect view of the lake and the mountains. More importantly, I could easily people watch. I always wondered what others were thinking about, listening to, or working towards.

I stripped off my black tank top, kicked off my sandals, and laid back with my book in the late morning sun. After an hour of reading, I realized how distracted I was becoming. The warm morning drew people outside in droves.

I chose this lake in particular, as it was in an active area with lots of runners, cyclists and roller skaters lapping the lake on the paved sidewalks. Fit women in sports bras and tight running shorts went bouncing by every minute.

There was a sex scene in my book, and I couldn’t help but look up at the athletic women jogging by – their perky breasts bouncing and curves accentuated by tight leggings. Was I a creep? Maybe. What’s the harm in looking from a distance? A casual glance.

[MF] Lazy Afternoon in a Hammock, Part II.

*Thanks for reading! You can check out Part I of this story* [*here*](https://www.reddit.com/r/gonewildstories/comments/v5uq5r/mf_lazy_afternoon_in_a_hammock_part_i/)*.*

I set up near trees near the busy intersection of several paved walking paths. I had a perfect view of the lake and the mountains. More importantly, I could easily people watch. I always wondered what others were thinking about, listening to, or working towards.

I stripped off my black tank top, kicked off my sandals, and laid back with my book in the late morning sun. After an hour of reading, I realized how distracted I was becoming. The warm morning drew people outside in droves.

I chose this lake in particular, as it was in an active area with lots of runners, cyclists and roller skaters lapping the lake on the paved sidewalks. Fit women in sports bras and tight running shorts went bouncing by every minute.

There was a sex scene in my book, and I couldn’t help but look up at the athletic women jogging by – their perky breasts bouncing and curves accentuated by tight leggings. Was I a creep? Maybe. What’s the harm in looking from a distance? A casual glance.