First time anal with Kelly [MF]

This is a long story, but I think it’s worth it!

Background on me:

Hi, all. My name is Kevin and I wanted to share some past sexual experiences of mine. Replaying them (and sometimes reenacting with my current partner) is a huge turn on.

All stories are almost 100% true. Some facts have been changed to hide any identification.

I’m mostly average – white male, 5’ 10”, 160 lbs., fit enough but I don’t try hard. Brown hair, full beard, and pale blue eyes. My cock is almost 7 inches long with a thick, wide head. Women always love that first insertion…

The woman in this story:

Kelly and I met when we were both in our mid 20’s. We met online (before Tinder/Bumble/whatever the kids use now!) and dated for almost a year.

She was short, about 5’ 2”, with fantastic curves. She wasn’t thin, but not exactly thick. Full D breasts with dark pink nipples and a plump ass. Kelly also had long dark hair that she loved to have pulled and sweet, light brown eyes. She also kept a fairly full bush but trimmed her bikini line. Perfect in my opinion.

The story:

We had gone out the night before. Nothing special. We went to a local restaurant for dinner and then had a few drinks after. When we got home her roommate was still up. She would normally be at her boyfriend’s place, but he was out with some friends.

Her roommate, Amanda, was nice enough, but pretty boring. We chatted with her for a while and left her to finish her movie on the couch by herself and Kelly and I moved to her bedroom.

As soon as the door shut we grabbed one another and immediately started making out. Tongues in each other’s mouths and hands running up and down our bodies. My hands traveled up her shirt to fondle her large tits, first over her silk bra and then pushing it up to feel their full softness and pinch her nipples, making them – and me – hard.

Kelly broke our kiss and pushed me away.

“Slow down! Amanda’s still up! At least wait until she passes out.”

“Ugh… fine,” I replied.

We decided to kill some time while waiting for Amanda to fall asleep and got ready for bed, being sure to tease one another as we stripped down. Kelly grabbing my semi-hard cock through my boxers and me slapping her ass as she slowly peeled off her jeans.

We got into bed, me in boxers and a pair of athletic shorts and Kelly in cotton panties and a large t-shirt, no bra, letting her hard nipples poke through the thin fabric. I love seeing braless women and hard nipples. It’s such a tease.

We turned on Princess Bride (a favorite movie of ours together), but the drinks and late night caught up to us and we passed out together.

The next morning we were woken up by the apartment door slamming followed by a car directly outside starting. Amanda was up and on her way out, probably to check on her boyfriend.

“Good morning, Kev,” Kelly said with a smile and half-opened eyes. It was an unintentionally sexy look.

“Hi there, sexy,” I said with a grin of my own.

I leaned over for a kiss, but stopped by Kelly pulling a blanket over her face.

“I have morning breath!” She exclaimed.

I replied, “I don’t care. I need to kiss you now.” Pulled the blanket down, rolled over on top of her, and leaned down for a wet, open kiss.

I pulled back. I could see in her eyes that she liked it and knew exactly where I wanted this to go.

“Let’s finish what you started last night.” she said as she pulled my face into hers.

I met her kiss, our mouths opening and devouring each other. My hand moved behind her head, grabbing a fistful of hair, and pushing her harder into my mouth.

We broke the kiss again. Lust in our eyes. Kelly sat up and pulled her shirt off quickly over her head and tossed it on the floor. My hands instantly moved to her breasts, gently squeezing them and rolling her nipples between my fingers.

She moaned as she pulled away from my face again.

“Fuck me now.”

She didn’t have to tell me twice. I rolled off to the side while reaching down for her panties, pulling them off and throwing them to the side. Kelly did the same with my shorts and boxers, my hard cock now free.

My hand returned to her now exposed pussy, feeling from her stomach, through her pubic hair, down to her warm lips. My middle finger easily slid down her wet slit.

“Is this what you want?” I asked as I slowly inserted my middle finger deep into her hot cunt.

“Oh, God!” She moaned. “No. I want that cock.” Kelly said, looking me in the eyes, as she grabbed her small hands around my thick member.

“Fuck me.”

I reached over to her nightstand and grabbed a condom out of the top drawer, ripped it open, and slid it over my penis.

I moved on top of her again and she positioned me at her entrance, my thick head parting her lips and feeling her wetness again. Once my tip was in, I slowly thrust my hips and filled her pussy with my full length.

“Ungh…” we both moaned together.

I started to pump slowly at first, but started to build speed. My arms held me up while my hips thrust into her. Kelly’s arms around my torso and legs wrapping around me.

“Fuck me from behind.” Kelly demanded. This was her favorite position and mine too! Like I said earlier, she loved having her long, thick hair pulled and I loved pounding her from behind, watching her thick ass shake with each drive into her.

Kelly got onto all fours while I moved behind her. I spread her legs wide and moved my cock to her pink pussy that was begging for me again. I wasn’t gentle this time and started fucking her hard as soon as I was in.

“Yes! Yes! Fuck! Yes!” She screamed.

She pulled her arms away and her face fell into the bed as I continued to fuck her.

Kelly brought her right arm behind her and rubbed her ass with her hand.

The next move surprised me. She brought her hand up to her face, gave her index finger a long, wet lick, and returned her hand to her ass. Her wet finger now circled her asshole and slowly entered.

“Fuck, Kelly! That’s so fucking hot!” I yelled while slowing down so I didn’t explode with this beautiful sight.

She continued to DP herself, finger moving in and out, as I held deep into her pussy.

She removed her finger and propped herself back up on all fours. She looked at me and said, “I need a minute. Lube is in the drawer.” And leaped off the bed and ran into the bathroom.

Left with a throbbing, hard cock, I was a bit confused. “Does she want me to fuck her ass?” I asked myself.

Neither of us was shy about our sexual history and had talked about our likes and dislikes. She had said her last boyfriend almost demanded anal all the time, and while it was something she enjoyed, didn’t want to be forced into. I respected this and had never tried or asked for it. I wanted to wait until she felt comfortable.

Apparently, that time was now!

I scampered across the bed, pulled open the drawer, and desperately searched for the lube.

“Found it!” I shouted to Kelly.

It wasn’t open. I unscrewed the top and tried to pull off the foil seal with my teeth.

“Success!” I smiled to myself as I watched Kelly softly run back to the bed with a huge smile on her face.

She climbed onto the bed, looked me in the eyes, and said, “Fuck my ass.”

She rotated and got back on all fours.

I squirted some lube onto my fingers and rubbed it in small circles around her tight asshole. I slowly pressed my middle finger into her. As I moved in further I could feel her hole tightening.

“Slow, please.” She said to me, eyes closed, biting her lower lip.

I gently pushed further and her hole accepted my finger. I started to fuck her with my finger.

“Oh… That feels good. Mmmm.” She moaned.

I pulled out, applied more lube to my fingers, and this time tried my middle and index fingers. Steadily I entered and heard Kelly breathe out, “Ohhh… yes…”

I found a gentle rhythm fucking her with my fingers as I started to rub my cock with my other hand.

“I’m ready. Fuck me now.” She said quietly, eyes still closed.

I lubed my rock hard dick and moved directly behind her, pressing my swollen head against her oiled button.

“Oh!” she screamed. “Go slow. It’s big.”

I took my time and continued to gently press in. I saw, and could feel, her asshole slowly opening up around my tip, and then was almost sucked in.

“Oh fuck!” I moaned. “You’re so fucking tight.”

“Just go slow. It feels so good.”

I slowly was able to insert almost my full length inside of her and began to gently thrust.

Kelly groaned in ecstasy as she began to rub her clit with her fingers.

“I’m gonna cum!” I yelled. My orgasm is quickly approaching.

“Fuck! Fuck! Fuck!” Kelly yelled as she furiously rubbed herself now.

“I’m cumming” I moaned as I moved my cock as deep as I could inside of her, and exploded into the condom.

“Ungh!!!” Kelly screamed as her legs began to spasm. “I’m… cumming…” she managed to get out.

We held like this for what seemed like 30 minutes, but was probably 2.

I slowly pulled out of her and used her T-shirt to quickly wipe up myself and her backside.

We collapsed together onto the bed, glistening in sweat and lube.

Unfortunately, this would be the only time we had anal. Kelly and I only dated for about a year. I still think about this day when I masturbate sometimes.

Let me know if you enjoyed this story and want to hear more stories. I’ll take any constructive criticism too!

Source: reddit.com/r/gonewildstories/comments/sz077o/first_time_anal_with_kelly_mf