By: JStraightFit – check him out on Squirt.org!
It was my first year of college, in the big city, independent and ready to explore. My class was a mixed group, studying Media, and I soon befriended a French girl, Marilyn, who was a mature student. She was pretty, always in 50s style dresses that showed ample cleavage, and she wore red lipstick with her hair in a black bob.
I was a moody punk-goth. Slim and fit, with a couple of tattoos, one pierced ear and long bang, shaved at the sides. I only wore black jeans or combats with DM boots, and all my t-shirts had their sleeves cut off. I’d already had some experiences with guys my age, and older, and was exploring my secret love of cock.
Marilyn and I spent hours at the student bar, sharing secrets. She loved asking me about my encounters with guys and encouraged me to share every detail, especially my games of strip poker with an older student at my previous college, which led to cocksucking and a very near fuck. I’d ended up naked on his bed with him rubbing his dick on my ass till he came all over my back and butt, but without ever penetrating me.
After a few too many glasses of wine, I had confided in her that I desperately wanted to feel a man’s cock inside me, and she thought JP was the perfect guy to break me in gently.
Marilyn told me about an ex-lecturer at the college who taught photography. He was in his mid 30s, gay, and loved younger inexperienced guys. He also liked to photograph them naked. She was desperate to set us up. I drunkenly agreed.
That weekend, she took me to his apartment in the center of town.
JP was handsome, blue-eyed with messy brown hair, about 6ft tall, slim and lean, wearing ripped jeans and a loose V-neck T-shirt with bare feet.
He invited us into his large warehouse space. It was full of industrial furniture and decorated with large black and white photographic prints, mostly of naked girls and guys.
Despite having a large dining table he arranged three cushions on the floor, and placed a bowl of snacks in the middle, with two bottles of red wine, and we sat down and started drinking.
I looked around the room as we chatted. At the back of the lounge space was a side-room with a large day bed, separated from the room by an open drape.
After a while, Marilyn excused herself and disappeared into another room. JP leaned in.
“So Marilyn told me all about your encounters with other guys. I was very turned on, and was excited to meet you. She says you want to try more?”
I told him about a few of my encounters and felt the blood filling my cock as we chatted and flirted, taking about all my first time sexual experiences.
Marilyn hadn’t come back.
Suddenly, JP stood up and offered me his hand.
“So, I think it’s time to take you to the next level. Let’s go somewhere more comfortable”.
He led me to the large day bedroom off the main lounge space. He didn’t bother to close the drapes as he stripped naked.
I watched him undress. He was slim but very muscular with very little body fat. His body hair was light, and I watched his large cock unfold as he dropped his jeans and underwear.
I undressed and joined him on the bed.
“So, when you were playing with this guy at college, he lay on you and rubbed his dick on your ass until he came?”
“Yes. It was intense.”
“And did you want him inside you?” JP asked.
“Yes, I did, but I think it was also his first time. He was as nervous as I was.”
“Well, let’s start there” JP said. “If it’s ok with you, I’ll lie naked on top of you, and we’ll see what happens next”.
I was surprised by his direct approach, but I liked that he was taking the lead.
I lay on my stomach on the bed and waited nervously while he climbed gently on top of me. I felt his naked warm flesh on my back, and then he lowered his large dick into place, resting it perfectly between my exposed ass-cheeks.
“Does that feel ok?”
“Yes” I replied. “It feels nice”
JP started moving his hips up and down, rubbing his dick along my ass crack, exactly as my friend had done before. The difference was that his dick was wet. He’d either added some spit or lube before climbing on top of me.
Soon his cock was sliding right up against my hole. He moved down an inch or so, and I could feel every part of his cock against me, including his wet tip.
I pushed back a little, opening my legs to give easier access. My dick was rock hard, pressed against the white sheets. He lay his full body weight on me and whispered into my ear.
“So, do you wish my dick was inside you?”
“Yes I do”. I whispered back.
He lifted his upper body and maneuvered his dick into a better position, and I felt the tip of his cock push against my hole. I was tight, but he persisted. He barely got his tip inside me. I was so nervous.
“Relax” he said. “I know how this feels. And you’re not my first virgin. The secret is to want my cock inside you. Do you want my dick in your ass?”
“I do” I tried to relax.
Slowly, his cock started to enter me. He was very patient, and pushed firmly but gently. After a while, he’d managed to get less than two inches into my hole before he met a second layer of resistance.
“Ok” He said. “Now breathe and try to invite my dick inside you.”
I wanted him so badly. He pushed in and I pushed back. Suddenly, his dick popped inside me another inch. I gasped a little.
He started a new rhythm, pulling out of me half an inch and then pushing back an inch, slowly gaining depth with each gentle stroke. It took several minutes of patient work, but soon most of his large dick seemed to be inside me. He lowered himself back onto me. And whispered again.
“Good. Now I’ll leave my dick inside you for a minute until you are completely relaxed”.
We lay there for a couple of minutes, and soon any pain melted away. I pushed back onto his dick. He took the hint, and started to very gently fuck me.
His strokes were gentle and slow, and very shallow. He barely moved in and out of me more than an inch, then two inches, and then three.
It took a good five minutes of slow fucking before he lifted himself up again and started to give me his full length. Soon he was really fucking me, pulling out almost all of his large, thick dick before plunging it back inside. It burned a little, but I didn’t care. I was his.
With his weight now off my back, I had the chance to move my head. It’d had been on the left side the whole time, and I needed to change position, so I lifted my head and flipped it to the right.
As I looked out into the lounge area, I saw Marilyn sitting there, just 6 feet away in her underwear, on a dining chair. She had one hand in her panties and was playing with her pussy. She smiled at me and I smiled back. So that’s how she got her kicks.
As JP fucked me, I imagined her view. A young punk college boy, pinned to the bed by a handsome older guy, plowing into his ass with a large, long cock. I closed my eyes and let myself enjoy the feeling of him owning my ass.
Soon his pace quickened, and his breathing got heavy. I was now fully relaxed and all the pain had given way to pure pleasure. I pushed back every time he entered me. It was bliss.
Then all of a sudden, he pulled out of me and I felt hot splashes of cum on my back. The first spurt landed between my shoulders while the rest fell onto my lower back, then my butt cheeks, and then onto my ass crack and hole. It was hot. Literally. Hot cum all over my ass.
JP leaned over, grabbed a white towel and started to clean me up. He was gentle and thorough, and soon I was clean and completely spunk free. I was also rock hard. Marilyn had watched the whole thing, and I was pretty sure I’d heard her orgasm too.
“Now you need to cum” offered JP.
He got up from the bed and led me by the hand to where Marilyn was sitting. He stood me in front of her as she remained seated on the chair in her lingerie. My erect cock was pointed right at her. JP stood aside.
Marilyn smiled up at me and leaned forward, taking my cock gently in one hand, she opened her mouth, stuck out her tongue, and started jerking my cock.
She licked the tip of my dick a few times to make it wet, and then continued jerking me off with wet fingers, while she held her mouth open, lined in red lipstick and with her tongue still out like a landing strip, waiting for my spunk.
I heard a clicking sound and looked over to my right. JP had a camera and was taking photos. I didn’t mind. He came in close-up and I heard the shutter taking multiple shots.
I let myself go, and spurted hot cum directly into Marilyn’s mouth. The shutter clicked. Every drop went between her red lips, but she didn’t swallow, holding my cum in her mouth. She let a creamy white river run the length of her tongue until I was finished. More photos and clicks followed.
JP pulled back, Marilyn closed her mouth, and swallowed my load. She looked up and winked at me.
“So, who’s hungry?” Said JP. “ I have food in the oven”.
