You come across lots of people in your life, and some you know instantly that you will be connected to them, always. It’s rarely clear what type of connection that will be. It can manifest as love, lust, fantasy- they can live forever as memory even if you only spent a moment with them. Of course, I would not dare to insult your intelligence, dear reader, by not implying the opposite of that spectrum also exists- be it obsession, sorrow, or hate. My dear friend Sissy was one of these connections. We had met at the tender ages of 15, and 14 respectively. We hit it off amazingly and became fast friends. Sissy was not particularly attractive. She weighed 250lbs or greater on a 5’8 frame. She had a round face and long brunette hair that she always pulled back into a pony tail.
Sissy was gay, she knew it- but this was back in the early 90’s where it was somewhat accepted but rarely spoken of.
Sissy is often the smartest person in the room, and she has a talent for writing and wordsmithing. She honed this talent as we grew older, and began to sexually mature, She would weave grandiose tales of her many lovers- both men and women. She would go into such amazing details of her sexcapades, and my 17 year old mind gave no resistance suspending that disbelief. Although we constantly talked about sex, strategized how to hit on girls we liked and such, we never took the plunge with each other. I was moderately attractive, charming and smart and chasing skinny, pretty girls. I’ll admit, it was a shallow time of my life. I also was not particularly attracted to her. Around my sophomore year in college, she came to visit me. I was going to college about 2 hours from the city we grew up in. It was not the first time she visited me while i was away.
Whenever Sissy came around, we would get absolutely wasted- there was always a party going on, and those parties always had beer, coke, acid, liquor, weed, pills,, whatever you liked.,
One night, after a few beer and a bong rip or two, we were sitting in my door, listening to music. The dorm had bunk-beds and she was hanging on the bottom.
“I’m really horny, Max.”, she said.
It hadn’t really occurred to me that I could have sex with Sissy. To be honest, although i suspended my disbelief during her stories, I never did believe them.
“Sissy, I don’t know what to say, I’m not all that attracted to you, you know?” “Max, I KNOW how much you like getting your dick sucked”- she was right. This was and is my absolute favorite sexual activity. In school, I had a reputation for being an “oral guy”. That meant a girl could come over and suck me off, I would reciprocate, and she would be on her way. I was a great fit for girls who didn’t want to have penetration sex yet, or with me, per se, but still wanted to fool around.
“That’s true”, I replied, “what are you asking?” “I suggest we made a trade- I’ll suck your dick, and you eat me out.” I considered it for what felt like an eternity. Did I want to add this layer to our friendship, was I interested in her sexually, would I function properly if I wasn’t into it? I had never been with a supple girl before and wasn’t sure if I wanted to.
In the end, my curiosity and sense of adventure guided me and I decided to go for it. I took down my pants, and underwear and revealed my cock. I hope, dear reader, that you not find me boastful when I say that I was blessed with a magnificent design- Long and thick, but not overly so, straight as an arrow at the base and the shaft has a slight curve toward the head, with a proportionate helmut. The phrase “you have a nice dick”, or , “you have a pretty dick” was miraculously commonplace.
Attached to that beauty of a tool was a average height, average weight, white male with a moderately attractive face.
She took my cock in her hand and pulled it toward her. She looked me in the eyes. She had a playful look about her. The moonlight shined through my door room window and all I could see was her face. When she put her mouth around me the first time, when i felt her amazing warmth envelope me, and the pleasure exploding from my toes to lymph nodes- i had an epiphany; This woman, my friend, was a knockout.
She worked my dick expertly. She would get it extremely wet with spit, stroke it back and forth while simultaneously swirling her tongue around the tip.
I could hardly take it- I pulled my cock out of her mouth, and began to undress her. I helped her remove her shirt and bra- revealing her enormous breasts- they were perfectly formed- and her brown nipples and areolos were perfecting centered. She stood up briefly to remove her pants and underwear. She faced away from me and gave me a perfect view of her amazing ass- large and muscular- apple shaped= and her glistening pussy was inviting me. I grabbed her ass, rubbing my dck between her ass cheeks. She smiled and said “that wasn’t the deal, Max”. She turned around and took my dick back into her mouth. This time, she was not playing. She grabbed my balls, and took my as deep into her mouth as possible. She spit, gagged, choked, coughed, whimpered, moaned- all the while stroking my cock and massaging my balls. I don’t have to tell you, I’m sure, that after a few minutes of sexual eternity, my balls began to tighten- and 10 or 12 ropes of hot white cum came spurting out of me. It was, by far, one of the best orgasm’s of my life. After a moment of basking in the post orgasmic peace, I knew that I needed to complete the deal- and I couldn’t wait. “Sissy”, I said, “That was incredible. I’m going to eat your pussy now” “Max”, she said, “I know you are not into me. I really just wanted to blow you. Don’t worry about me”. “Sissy, I am going to lck your pussy in about 10 seconds. If you don’t want that, get up and leave the room” I backed off and waited. At the count of 10, I dove face first into her pussy. It smelled incredible- warm and musky, like woman, like life. I kissed her tights, cupped her ass, and finally, touched the tip of my tongue to her swollen clit. She shivered and yelped. She grabbed my hair and ears. She was ready. It was time to get to work. I fucked her with my tongue, darting it in and out of her pussy, forcefull, then soft. I kissed her lps, sucked on them, ran my tongue up her clit. I worked her clit softly, applied pressure, made circles- i used every method I had heard about and some I was improvising on the spot. She squealed and cried, moaned and laughed- i let her guide me and eventually, I got to her place. I took her clit in my mouth and began to suck it. The constant pressure and friction hit the right spot and she began to write underneath me. She was so powerful, I could hardly hold her down. I kept the pressure on and tickled the entry to her cunt with my fingers. She was extremely wet. I faintly heard her whisper “ok”. I sank my fingers into her pussy- they took them in willingly and immediately. I began to finger fuck her slowly, while sucking her clit, and then I felt her pussy walls begin to spasm around me. The force was so stong I couldn’t pull my fingers out. Eventually she lifted my head from in between her legs and i removed my finger from her. She cupped my face, with content in her eyes and said, “Max, I love you, but I ain’t going to kiss you. We’re friends, that would be weird”. We snuggled together, falling asleep, satiated and happy. Read more »