The Night We Switched and my best friends girlfriend let me cum inside her [FM]

So, back to the question. I looked down at Stephanie. Her blue eyes sexy as fuck looked at me and she gave me a shoulder shrug and approval of “sure, why not”.

“Yes, we are down. Meg, you good with this?” I asked.

“Ofcourse, just fucking get over here.” She said with an embarrassed and playful tone.

I made my way the the bed. Ryan came to the floor.

Meg starts lifting her hips up and taking off her jeans. Feet still on the floor. No eye contact. She pulled her leg fully out of her jeans. She was just in her top and bright red silk panties. She motioned for me to come over to her. Sexy yet shy.

I looked into her hazel eyes. She bit her lip ever so slightly and we started to kiss. I could taste Goldschlager or some peppermint schnapps on her lips. Very festive.

She was a slow kisser. Her tongue would always linger a little bit longer in my mouth. It was hot as fuck and sweet little Team Mom was turning into a fucking sex pot. This was fucking exciting.

The Weekend: Molly, my roommates ex-gf [f] [20] and the most sensual and sexual night of my life

This happened a while back when we were in college.

To this day, it is still one of the most intense nights and weekends of my life.

A quick back story:

My roommate, Kyle and I had started dating two girls who also lived together. I was dating Katelyn and he was dating Jennifer.

Katelyn and I stopped dating after a couple of months. Come to find out she was totally bat shit crazy. Jennifer also ended up moving out.

Jennifer and Kyle continued dating and we would all frequently hang out together.

A little more about her, Jenn had jet black hair just to the bottom of her shoulder, pretty face (think a bit of Mila Kunis mixed with a bit of Natalie Portman) she was not as drop dead gorgeous as Mila, but she was attractive. Very attractive.

She had these deep brown doe eyes, the kind that would focused intently on you during conversations.

The kind you could just get lost just looking into.

She carried a solid B cup chest and a uniquely hour glass like figure. Approx 115 lbs, but a super small waist with a bubble butt in the caboose.

My First Time with a Cougar [30] [f] who Pried Me [m] [21] Out of My Bartending Shift

This story takes place a few years back. I was twenty one, in college and worked as a bartender at a sports bar just outside of downtown.

Although I lost my virginity in High School, and had a pretty consistent and solid sex life, I had always been girlfriends both in HS and College.

I had recently broken up with my girlfriend and just started to hook up with some of the girls at school who I knew and hung around with frequently.

That said, I’d never had a one night stand, nor had a hooked up with a customer from the bar and I had never been with an older woman.

Soon enough this would all change. Looking back on it, I was pretty naive about a lot of sexual things, but I digress.

The bar. It was a cool place. Private owner (non-corporate), great clientele, a handful of regulars and a solid staff. Most of us were in college or had recently graduated, it was very much the fun, vibrant grab-assy type of staff that I’m sure many of you who have bartended or worked in restaurants can relate to.

The Night I Accidentally Had Sex w My Close Friend 23 [f] Molly but Very Purposefully Came Inside of Her the Next Morning. [M F] NSFW. TRUE STORY

To fully appreciate this story, I’ll take you back to the beginning and a quick background about how I met Caley.

It was a Sophomore Speech Comm class. Small class of 15-20 students and we sat next to one another and started talking before class.

That would be a conversation that would ignite a friendship, relationship and many firsts that would occur between us.

A bit more about her. Her name was Caley. Her grandparents were of Eastern European descent, mostly Polish, but she grew up with hippie parents in Colorado. She was a total free spirit with natural beauty in her features.

5’ 5”. Blonde hair that cascaded to her middle back. Almond shaped Green eyes, blonde eyebrows with a small circle eyebrow ring, fuller than average B/C cups a tight petite body. She wore minimal make-up and a porcelain like Nordic complexion.

We would ultimately have a lot of firsts together in our relationship. But to get to this story I will need to gloss over how we got here.

Shortly after we met, she was the first person I tried Molly with. We had an amazing night. Got naked, fooled around (I possibly fell in love), but we never had sex. Just touching, making out— more sensual than anything.

Adventures w/ Stephanie— The Night She [f] [24] Gave Me the Remote to Her Panties at the Bar and the Awesomeness that Ensued on the Drive Home

Interestingly, I had a couple of comments/upvotes asking about Stephanie and had a few people reach out via DM wanting to know more.

Quick refresher. Stephanie is about 24. She has long brown hair that cascades to the small of her back. Captivating light blue eyes. Super tight and athletic body. Solid B Breasts.
Tribal “tramp stamp” tattoo on the small of her back and a pierced belly button.

She just kinda looks like she wants to fuck. Very sexy. Not cute. Even when I first met her, this was my first impression.

We ended up dating off and on after this story.

Adventures in Holiday Party— The Night We Switched and I [m] Got to Taste My Best Friends GF 21 [f] and So Much More… from gonewildstories

Stephanie has a sexual appetite and sexual awareness that I have rarely seen. If sexual intelligence was a skill set, she would probably have the equivalent of a fucking Doctorate degree.

This story took place about a year after the last story. It is probably my best Stephanie story.

Adventures in Holiday Party— The Night We Switched and I [m] Got to Taste My Best Friends GF 21 [f] and So Much More…

This happened after a Holiday party at the bar I worked at few years ago.

QUICK BACKSTORY:

I was working as a bartender at a sports bar in college. Around November, a super close friend of mine, Megan, reached out to let me know her restaurant was closing and wanted to see if I could swing a job for her. I did.

To give some back story on Megan. She is about 5’ 5”. Light skin, brown hair, hazel eyes and fit. She is more cute than sexy, she is super nice but also has a mystery in her smile that is hard to put into words. A mysterious sexiness in her smile.

At any rate, it is important to note that she is my Best Friends Girlfriend. Megan and Ryan had been dating for 2+ years. We were all super close.

We hung out together all of the time. If we weren’t at their house, they would be at ours. I probably saw Ryan and Megan 4-5 nights a week.

The Night I Accidentally Had Sex w My Close Friend 23 [f] Molly but Very Purposefully Came Inside of Her the Next Morning. [M F].

To fully appreciate this story, I’ll take you back to the beginning and a quick background about how I met Caley.

It was a Sophomore Speech Comm class. Small class of 15-20 students and we sat next to one another and started talking before class.

That would be a conversation that would ignite a friendship, relationship and many firsts that would occur between us.

A bit more about her. Her name was Caley. Her grandparents were of Eastern European descent, mostly Polish, but she grew up with hippie parents in Colorado. She was a total free spirit with natural beauty in her features.

5’ 5”. Blonde hair that cascaded to her middle back. Almond shaped Green eyes, blonde eyebrows with a small circle eyebrow ring, fuller than average B/C cups a tight petite body. She wore minimal make-up and a porcelain like Nordic complexion.

We would ultimately have a lot of firsts together in our relationship. But to get to this story I will need to gloss over how we got here.

Shortly after we met, she was the first person I tried Molly with. We had an amazing night. Got naked, fooled around (I possibly fell in love), but we never had sex. Just touching, making out— more sensual than anything.

Close Friends [mf], Molly and the Night I Finally Came Inside My College Crush More Than 2 Yrs in the Making… Part 1

To fully appreciate this story, I’ll take you back to the beginning and a quick background about how I met Caley.

It was a Sophomore Speech Comm class. Small class of 15-20 students and we sat next to one another and started talking before class.

That would be a conversation that would ignite a friendship, relationship and many firsts that would occur between us.

A bit more about her. Her name was Caley. Her grandparents were of Eastern European descent, mostly Polish, but she grew up with hippie parents in Colorado. She was a total free spirit with natural beauty in her features.

5’ 5”. Blonde hair that cascaded to her middle back. Almond shaped Green eyes, blonde eyebrows with a small circle eyebrow ring, fuller than average B/C cups a tight petite body. She wore minimal make-up and a porcelain like Nordic complexion.

We would ultimately have a lot of firsts together in our relationship. But to get to this story I will need to gloss over how we got here.

Shortly after we met, she was the first person I tried Molly with. We had an amazing night. Got naked, fooled around (I possibly fell in love), but we never had sex. Just touching, making out— more sensual than anything.

The Afternoon That I [M] Unexpectedly Came Inside My [F] 23yr old Hair Stylist Before She Moved to Seattle with Her Boyfriend

It was one of the most fulfilling, unexpected and best afternoons of my life.

I had been getting my haircut at the same place for the past 11 months. My stylist, Crystal had the ideal girl next door look. She was 23-24ish, long shiny brown hair with big brown eyes, one dimple and a laugh would reveal a seductive sideways smile when you said something in just the right way.

We always had a good rapport and a somewhat flirty relationship, but never anything more than I assumed she had with other customers.

This particular day, she gently put her soft hands on the back of my neck and said, “I have some bad news for you?”

“Oh yeah?”, I asked.

“Yes”, she continued, “my boyfriend and I are moving to Seattle. It’s for a job opportunity for him and we will be gone in two weeks.”

“Bummer”, I said, not sure if she could sense my disappointment.

As she continued with the finishing touches of my neck massage she stated, “so maybe we can finally grab a drink before I go?”

“For sure.” I said. “How much longer to you work tonight?”