I’m at work right now, bored as hell, and I’m wondering if I can right a decent story in the two hours I have left. To make a little easier I’ll go with something almost true. Here goes.
My first relationship (Mf)
It was 1995 and I was a 21 year older stoner living in my mother’s basement. I did odd jobs now and then to pay for weed and was soon to wear out my welcome. Mom owned a business and worked hard to support my two younger sisters, 13 and 16.
One day mom asked if I would help her by stuffing envelopes for a promotion. She had also recruited one of my sister’s friends for the job. She paid me $10 an hour to fold a piece of paper and stuff it in an envelope while I sat on the living room floor watching reruns of Ren and Stimpy
At 10 AM there was a knock on the door. My sister’s friend Jen was dropped off by her mom. She was very cute. About 5’2″ blonde, blue eyes, B cup breasts and a round bottom. She wore a pink polo top and a white pleated skirt that stopped just above the knees. Very preppy.
“Hiiee, I’m Jen, you’re Mom said you’d be here to help out with the mailers.”
“Yeah, I just got started.” I replied “I’ve got everything spread out on the floor in the living room. Can I get you anything to drink?”
“No thanks”, Jen replied with a beautiful smile through glossy pink lips and a surprising amount of eye contact.
I had my spot kind of cleared out and I pushed the coffee table out of the way so she could sit across from me. I sat down and gathered a stack of letters for her to fold, with the envelopes stacked within arms reach between us.
We chatted about my sister and school stuff, I went to the same school 4 years ago. Lunch time came and I made us sandwiches which we ate outside.
“Do you smoke?” I asked he as I pulled a joint from my cigarette pack. “Yeah but I don’t want your mom to catch me.” She replied.
“She won’t, she doesn’t get home until 6 or 7 tonight.”
We smoked up while sitting on the porch swing and I couldn’t help but glance at her pink knees and about four inches of thigh exposed by her pleated skirt. I felt a definite tingle and I think she could feel it to. I got up and grabbed my ice tea and sat back down but a little closer so I could feel the heat of her skin next to mine.
After lunch we plopped down on the carpet to continue our work in a very relaxed state. Jen sat cross legged in front of me and I could seel the pink flesh of her inner thighs clear up to the smooth cushion of cotton fabric stretched over her 16 year old pussy.
I felt a strong current of electricity surge down my spine into my crotch. Fold the letter, grab the envelope, put the letter in the envelope, repeat. As Jen reached for the envelope I tried to glance down her polo shirt without her noticing. I can’t swear she didn’t notice but I don’t think she cared. The soft curve between her breasts led to the white lace trim on a pretty pink bra. Her cheeks looked red and I steered the conversation.
“Do you have a boyfriend Jen?”
“I’ve been seeing someone for a couple of months. His name is Dave and he goes to school with us.”
“What are you guys up to tonight?” I asked.
“We’re going to a party at Lauren’s house while her parents are in Italy.”
I knew Lauren, she was cute, and a close close friend of my sister’s. I’m sure she wouldn’t mind if I stopped by the party.
“You should come! Your sister will be there.”
Jen’s mom came and picked her up at 4 and I raced to the basement to whack off. I just kept picturing her tight panties stretched across the heavenly curve of her outer labia. I just knew it was tight, pink and delicious. I had to hook up with her.
I went to the party. Walked in through the side door which led to the kitchen and dropped my beers off in the fridge. I grabbed one for myself and accepted the fact they would all be gone the moment I turned around considering the average age of this party was 16 or 17.
“Oh my God, you’re Lisa’s brother. What are you doing here?” One of the girls asked me as I stood in the kitchen.
“I was invited, by Jen. Have you seen her around?”
“She’s out side, I think she’s fighting with her boyfriend.” Uh oh. I don’t want to get involved with that. I’ll just play it cool and see what happens. I smoked a joint in the yard and teenager after teenager asked me for a hit, and they had a bad habit of bogarting the joint.
“Hey you made it!” I heard Jen’s voice as she approached and did a kind of run-jump-hug. I felt her firm breasts push into my chest as I wrapped my arms around her. My dick immediately jolted and swelled a bit.
We walked back in the kitchen and talked for a while, another friend of hers joined and I could tell these girls had something of a crush on me. I’m not surprised. I’m the cool older brother if one of their friends and I’m not bad looking.
“Someone said you were in a fight with your boyfriend, everything okay?”
“Whatever, he left.” She replied.
“Would you go and get us more beer? Pleeease.” Her friend was actually begging.
I quickly agreed and Jen unsurprisingly elected to go with me. We hopped in my car and she sat again with her legs parted, her skirt hanging slightly between her legs, easily six inches above the knees. We pulled into the parking lot of the liquor store and our lips were drawn instantly together. Inheld her hand in one hand and felt her straight blonde hair thread my fingers. I gently squeezed her neck as we turned our faces to slide our tongues inside our mouths.
I reached down and placed my hand on her pink thigh and felt the soft smooth skin of a true blonde. She’s never shaved this high in her life. She barely had any hair in her legs. What was there was a smooth and fine. She moaned slightly and I slowly walked my fingers up her thighs until I felt the cotton panties brush the side of my finger. It was very warm and soft. I pushed into it finding the cleft between her outer labia. I rubbed up and down gently as I pressed my hand into her. She moaned again.
Jen’s hand reaches down for my cock and she was not disappointed. I was rock hard and curved against the denim if my jeans. She stricked it through my pants and it tingled and pulsed. With my forefinger I found the ridged edge of the fabric of her panties and pulled it over her pussy mound. It held in place as I gently rubbed her pussy with my hand, not pressing into her but lightly brushing the surface, orienting myself to the landscape.
She had a fine coat of pubic hair with just a slight curl. There were no inner labia protruding from her mound but as I pressed my middle finger into the crevice I felt a hot wet spot and curled my middle finger inside her. She drew her breath and buried her face into my shoulder. As I moved my finger around inside her she dug her nails into my shoulder, a slight cry escaped her lips. “Don’t stop” she lightly cried into my neck. She began kissing my neck and I loved the feeling of her warm breath.
My middle finger was soon joined by my ring finger and I began carefully plunging my fingers in and out of her very wet pussy. I sat back a moment and withdrew my hand from beneath her skirt. My fingers were glistening with her juices and she seemed slightly embarrassed.
I didn’t want to get busted in the parking lot of a liquor store with a 16 year old in my front seat. “I’ll be right back.” I declared as I hopped out of the car. Seven paces and I thought it’d be safe enough to smell my fingers. They smelled clean, a light scent of soap and a light scent of woman.
I returned to the car and dropped the beer into the trunk. As soon as we got in the road Jen repositioned herself in her seat and reached to unzip my jeans. As she got hold of the zipper I reclined my seat as far as I could and still drive. She pulled.my dick through my loose boxers and jeans and kissed it right in the head. “I’ve been wanting to do this since the first time I saw you.” She said.
“When was that?” I replied curiously.
“Last year when we came back to your house after the school recital.”
Oh my gosh, that’s right! Jen was in choir with my sister and I must have seen her before, but I truly never noticed her. She was making quite an impression now though. She went down on my cock with her very firm and voluptuous lips. She stroked up and down with her mouth as I carefully navigated the back roads to the party. The head of my cock stiffened and the head swelled with a pulsing urgency to come in her mouth.
“Will you fuck me?” She asked candidly. Of course I replied and she began to swing her right leg over my lap. “No no no!” I said urgently not like that, turn around and sit on my lap like you’re driving. She swung her left leg over the console and I pulled her around her waist as she slid over fully on my lap. And we stopped at a red light. It was 11 at night on a quiet road in suburban America and just one or two cars passed in front of us, thankfully no one pulled up behind us.
She grabbed the steering wheel while we were stopped and I reached under her pulling her panties to the side. My fingers found her wet pussy and I pointed my dick straight up into her. She slowly lowered onto me and I felt the full weight of her pressing into me. Her soft round ass cheeks felt incredible.
The light turned green and I took the steering wheel and pressed the gas. Once we got to speed Jen pressed her left hand on the door’s window sill and her right hand on the back of the passenger seat. She lifted herself up and I felt her slippery pussy slide smoothly up the shaft of my cock then press down hard to the base as her round ass hugged my hips.
Jen steadily continued her ministrations as I drove down the road at the speed limit. I was in no hurry to get to the party. I held the steering wheel with one hand and slid the other up her shirt and roughly under her bra Soni could squeeze her breast she moaned and I squeezed her nipple between my fingers. She fucked me harder, and began curling her pelvis once she reached the base. I could feel her cervix with the tip of my penis and crept closer to my orgasm.
I pulled into their driveway and parked behind som very big SUV’s so no one would see us. I opened the passenger door and she swung out, we both did. I held her hand and led her to the hood of the car. It was very warm from the drive and I bent her over it face down. I flipped up her skirt and pulled her panties down to her knees. My pants dropped quickly to my ankles and my dick pointed straight as a weathervane seeking a source of warmth and sunshine. I reached down with my hands, my fingers in the crease between her thighs and cheeks, and spread them revealing her pink insides. I pushed my cock forward and entered her completely. I moved my hands around to the front of her hips and began thrusting powerfully into her. Her ass cheeks slapped against my legs as I pounded her. She made whimpering sounds of pleasure, short pleas of harder, deeper, yes yes yes.
“I’m gonna come” I declared. “In my mouth” she replied. I pulled out of her glistening as she turned around with a real sense of urgency. She reached for my cock with her hand and began stroking with purpose as she sucked on the head.
Now it was my turn to whimper. Oh my god, oh my god, I’m cumming. She just kept sucking, and swallowing, and sucking, and swallowing. Never in my life have I seen someone sperm with such desperate enthusiasm. She squeezed the base of my dick hard and ran her thumb up the length of my urethra squeezing the very last drop into her tongue, and quickly swallowed.
Jen stood up and pulled her panties up over her sweet ass with a flip of her skirt. It was official, I was in love. We would faithfully be together for two years after this night, and friends (with benefits) for 10 more. There are so many good stories I could tell. Do you think I should?
By the way, I finished this story in two hours and ten minutes.
Source: reddit.com/r/sexystories/comments/cdadd1/my_first_relationship_mf