Massive Ass Play with a Friend [MF]

Shortly after graduating college, I moved to a new town where I didn’t have many friends close by. This led to me cruising facebook a lot to find old acquaintances that lived in or near my town. During this time I reconnected with an old high school friend named Amanda. She had always had a crush on me, and I always thought she was cute, but we never dated. She was still adorable. She was 5’6” 140 lbs with curly brown hair and lots of freckles (which I love). She was not well-endowed up top with just A cup tits, but her booty was wide and plump… just the way I like them.

Now for the bad news… she lived 4 hours from where I was currently living. Bummer. But that didn’t stop us from messaging constantly on facebook. At first our messages were innocent and rehashing old memories. Then I got flirtatious by teasing her about her crush on me and saying how it was too bad we didn’t live closer. She shot back that I wouldn’t be able to handle her as she had gotten a bit more wild since high school. This piqued my interest. Just how wild?

First time anal with a long time girlfriend [MF]

During my final year in college, I met and began dating Jackie. She and I hit it off immediately. We were into the same bands and movies, and shared a similar sense of humor. It also helped that she was adorable. She was 5’4″ 120 lbs. Dark shoulder length hair and hazel eyes. She had some curves too. Only a 34B up top, but her ass was PHAT! I grabbed at it every chance I could, and she would tease me relentlessly with it too.

Once we graduated college, we found jobs in the same area and got an apartment together. Most mornings and weekends were spent lounging around where she would be in a t-shirt and a thong, wiggling her ass around trying to get me riled up. Most times it worked for sure. I was always 100% honest about my desire to fuck her in the ass, but she would always say “I’m sorry, baby. No.”

One Spontaneous Night with a Good Friend [MF]

I had met Rachel during my sophomore year of college. I immediately thought she was gorgeous. She was 5’2″, maybe 110lbs on her heaviest day. She had wavy, light brown hair and bright blue eyes. She had cute little A cups, but an ass that should have been on a girl twice her size. She reminded me a lot of Kerri Russell, which she got told a lot.

Anyways, since the moment I met her, she had always had a boyfriend. However, during the start of our senior year, they abruptly broke things off. It was a rough break-up, and she spent a lot of time venting about it to me. This is ultimately what brought us closer together. We spent many afternoons and nights just hanging out, watching movies, making dinners, drinking cocktails. I was honestly just into her for the friendship at this point. I actually had my eye on a different girl at the time, so I truly was not expecting what happened next.

My experience with a cumslut [MF]

During my 4th year of college, a friend of mine moved into an apartment complex that seemed to be teeming with 2nd year girls. On one side of him lived Jocelyn and Shawna. Jocelyn was about 5’0″, curvy with dark hair and eyes. She had put on the freshman 15 quite obviously, which ballooned her tits to at least a D cup. She was a bit immature, which wasn’t my type, so I wasn’t super interested. Shawna was taller and thinner than Jocelyn, and thus less curves. She was gorgeous though with dark hair and huge hazel eyes. She also had this sexy voice that drove me nuts. My friend had a huge crush on her, so she was off limits.

One of the other side of my friend lived Kelsey and Sharon. Kelsey was a bit of an enigma. She was above average in looks, breasts, ass, personality, etc. but we never really clicked. Come to find out, she came out as a lesbian years later. Go figure. Sharon on the other hand was just my type. She was 5’10”, thin, blonde hair, green eyes, freckles on her nose, cheeks and shoulders. She had perky B-cup tits, a tight little bubble butt, and legs that went on for days. I immediately gravitated towards her, and committed to getting her in bed.