A Sexy Summer Short

This is my entry into the Summer Lovin' Story Contest 2022. I always like to reinforce that like my author name says, all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers.

Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories. I also love when people guess in the comments what parts are "Truth" and what I added for "Twists"

Everyone in the story is 18 years of age or older.

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INTRODUCTION: If you've read any of my other stories, most of the women I describe remain consistent:

• Sherri - my current wife of over 20 years
• Tara - girlfriend from grad school who was open to anything, and I mean anything, in bed
• Jess - the nice girl that I screwed over (both physically and emotionally)
• Kat - college girlfriend who cheated on me

Other women passed through my life at times, some for more time, some for less. But there was one time-period that was more active than others. It was in the early 90's - the summer after Kat broke up with me. I made the decision that for that one summer there would be no relationships, no falling in love, just dating around and enjoying myself - and enjoying as many willing women as possible.

This is the first story of that summer. If it's well-received, maybe this can be a series of "Sexy Summer Shorts" that continues in the future.

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I was 22 and working in the accounting department of a local hotel getting some experience before leaving for graduate school in the fall. One of my co-workers, Elaine, mentioned that she wanted to introduce me to her little sister, Heather. Elaine was older than me and engaged but knew me well enough that she felt comfortable with me asking out her 18-year-old sister.

I called Heather, we chatted and picked a night to go out later that week. Heather still lived with her mom but was heading to college in the fall. So, for the first time in a few years, I had to do the awkward "meet the parent" when picking up a girl for a date. When Heather came down the stairs, I was psyched. Where her sister Elaine was sort of a frumpy, plain, brunette, Heather was the exact opposite.

She was shorter than me with a lean body highlighted by a pair of skinny jeans. She was wearing a crop top that showed a hint of a toned stomach with a belly ring. Her breasts were small and perky, slightly bouncing under her top. Heather had long blond hair that fell to mid-back and her makeup looked light and natural which set off her bright green eyes. She was naturally attractive, and her entire vibe was that she was the type of summer girl the Beach Boys would have written and sung about decades earlier.

We left her house and went on a very typical first date. Dinner, coffee, then a walk around a local outdoor shopping center. Because she was under 21, neither of us drank on the date and she was definitely younger and at a different point in life. She was still basking in the memory of her senior year in high school and excited about leaving for college. Fortunately, we had similar tastes in music, movies and TV so despite the differences, we got along pretty well. Heather had a curfew from her mother of midnight, and we made it back in plenty of time. I gave her a kiss on the cheek, and we planned a second date.

I was still working and dating other girls while Heather was spending time with family, friends and most likely guys at the same time. But we seemed to like each other enough that we would get together at least once if not twice a week.

As we continued to go out, the kisses moved to her mouth, then got more aggressive. We made out at the movie theater and in my car. When I had a day off, we went to the beach, and I got to see her in a bikini for the first time. Her body had all the advantages that youth brings, nothing sagging, everything pert and tight. At one point, we were both in the water, sort of playing and bouncing in the waves, when Heather swam over and wrapped her arms around my neck and legs around my waist.

As we started kissing, I could feel myself starting to swell in my bathing suit. I tried to shift so that Heather wouldn't be able to feel my erection, but she tightened her legs even more.

"Nope. I want to feel you." She said into my ear. Our kisses got deeper as the waves bounced her thinly covered crotch against my swollen unit. Heather used her legs to tighten her grip and began to breathe against my neck. Her pelvis was grinding against me, and her breaths got shorter and more frequent. I had my hands on her ass, gripping her naked cheeks under her bathing suit bottom.

All of a sudden, I heard Heather start to whimper and her whole body seized around me. I felt her hips buck once...then twice...then her whole body went limp.

"Fuck that felt good." She spoke. Heather let loose her grip and kicked away from me in the water. I could tell that she was readjusting her bikini underwater as it had gotten a little twisted from our activity.

Swimming back, she climbed up on to my back and kissed my neck and face.

"Sorry you're so hard. If you can wait, I'll help you out when we get out of here."

The rest of the day was fun, but uncomfortable for me. It felt like my dick would never fully deflate and I spent a copious amount of time trying to hide it from everyone on the beach. Plus, my groin was aching from a classic case of blue balls. Later in the afternoon, we left the beach, grabbed dinner at a nearby seafood shack and hopped in the car to bring Heather home.

As we neared her house, she told me to turn down a street a bit earlier than usual. The street led to an office park that was obviously closed for the weekend. Heather directed me to the back of the parking lot and down a second hidden driveway. This led us to an old empty lot that looked like it used to be used for overflow parking. I guided the car into a corner as Heather adjusted her position and leaned over the console to my seat.

Heather reached up and gripped the sides of my shorts, guiding them down and over my hips. My sore, flaccid dick started to come to attention as she took it in her mouth and began swirling her tongue up and down its length. As my cock grew in her mouth, Heather worked her way up so that her lips were around the sensitive skin at the head, licking and sucking before plunging back down the entire length.

I had never really talked to Heather about how sexually experienced she was, but she definitely had some natural talents when it came to giving head. She took my dick from her mouth and started licking up and down my shaft like a summer popsicle. Her tongue traced every inch of skin and the engorged veins that throbbing up my length. Heather was able to take one of her hands and started to stroke me while she returned to swallowing my dick.

After all the teasing that day, I knew I wouldn't last long, and I felt my explosion building. I had my hand resting on the back of Heather's head as I felt the cum begin to boil.

"Heather, I'm gonna cum" I warned.

Heather backed off my cock, keeping just the head in her mouth as I shot my load. I felt her mouth fill with my seed and heard her gag slightly. As I still dripped out the remnants of my orgasm, Heather sat up quickly and grabbed her empty soda cup from the holder in the car. Prying off the top, she spit my load into the cup and used a napkin to wipe off her lips and chin.

Smiling up at me, she said, "Swallowing is gross, but hope that made up for today a bit." I drove her home and we made plans for later that week.

On our next date, we met up on a Saturday morning and decided to spend the day at my place. That summer, I was renting a house in the suburbs with two roommates. The house was owned by my buddy Jim's uncle who had moved out years ago but rented it to whatever family or friends needed it at any given time. It was technically three floors, so we each had some space. Mac was in the converted basement which was the largest space. Jim was on the middle floor with the kitchen and most of the living area. I was in a converted attic which gave me room for a sitting area, TV, bed and my own small bathroom with a shower.

The two best parts of the house were that it had an inground pool in the backyard and the converted attic/loft that acted as my bedroom. There was a grill by the pool and an outdoor staircase that ran from the patio all the way up to a door to my loft. During colder months, I could enter my room through the house, but in summer, I usually just opened the gate, walked by the pool and ran up the exterior steps to my room.

Anyway, we spent the day by the pool with my housemates and a random collection of friends. That day, Heather was in a different, but equally revealing bikini. She was matched, however, by some of the other female guests and girlfriends who gathered around that day. For the guys, there was a collection of boobs and booties of all shapes and sizes on display all afternoon. Admittedly, while some of the girls were older and bustier, I was still mesmerized by the young, lean shape of Heather.

We all swam, smooched and relaxed enjoying the summer day. Both Jim and Mac alternated between sneaking glances at Heather's body and giving me different versions of thumbs-up when she wasn't looking, which earned Mac some smacks from his girlfriend. Some of the group disbursed and left while the remaining folks all grilled some food and had some drinks (yes, I gave booze to an underage girl) as we lounged into the evening.

Once the sun when down, Heather and I mutually decided to head up to my loft before I had to drive her home later that night. As soon as we got into the room, we fell on to the small sofa I had in one part of the room, by the door. Heather still had on her bikini and had pulled on a pair of Daisy Duke denim shorts. I sat on the couch and Heather straddled me, as we started making out.

My hands moved up under her top and I started cupping her small tits and playing with her hardening nipples. With our mouths locked together, Heather was grinding her pelvis on my bathing suit-covered crotch. I was able to reach behind her and undo the straps on her top releasing her breasts. I grabbed her by her back and pulled her toward me. I started sucking on her small tits and licking her nipples, switching back and forth. Her tits were small enough that I could cover them with my entire hand and take most of them into my mouth at any given time. I could feel Heather's small nipples tightening and perking up as I added suction. Meanwhile, she seemed to have found a way to get the seam on her denim shorts to rub against her covered pussy and she was pushing herself closer and closer to an orgasm. The scent of her pussy started to fill the warm room as her breaths got faster.

Suddenly, I felt Heather's body seize up against me as she bit down on my shoulder through my shirt in the throes of her orgasm. She groaned and continued to grind her pussy against me as she rode a small second wave. We were both sweaty from our activity and the hot, humid summer air. We locked our sweat covered lips together again before Heather said, "Get a condom and let's move to the bed."

We separated ourselves from the couch and I went into the adjoining bathroom to grab some condoms before returning to the bedroom. Heather was completely naked, laying on top of the sheets. Her body was lean and tight, and her boobs didn't fall to the sides at all, despite laying on her back, staying pert and upright on her chest. She had her knees bent with her feet planted on the mattress so I could see the folds of her wet, glistening pussy. At her crotch, she had a light blonde patch of fuzz that was visible but well-trimmed.

Seeing her fully naked in the light for the first time I was entranced with her distinct tan lines. Her skin was bronzed from the summer sun, but her tits and pelvis showed just how pale and almost translucent her natural skin tones were. There were some thin, slightly lighter strips on her shoulders and on her hips from when different bathing suits had been worn throughout the summer. Even now, close to 30 years later, I openly admit I love the look of tan lines on a woman and Heather is partially responsible for that.

As I walked toward her, condoms in hand, a thought flashed into my mind:

"Uh, Heather, we've never talked about this, but are you a .... Uh...". Fortunately, she saved me from continuing with a laugh.

"No. I'm not a virgin. I've been having sex since my junior year with my old boyfriend."

"Well, in that case, what's your pleasure?" Yeah, I heard the cheesiness, but fortunately Heather ignored it.

"I want you on top of me. My puss is so fucking wet right now. I want to feel you inside of me." She spread her legs even more as she spoke, inviting me over.

I rolled the condom over my rigid cock and laid between her legs. I'm just about 6 feet tall and what I've always described as "perfectly average" in the dick department. Despite the fact that her pussy was dripping from her recent orgasms, the head of my cock felt immediate resistance as I tried to push in.

Heather let out a groan and was shifting and rotating her hips to try to help me press forward. I pulled back slightly and instead ran the length of my cock up along her slit, spreading some of her natural lubricant over myself. As I worked my way back down, I would put the tip of my cock slightly inside her, lubing it up more, as well.

Heather's clit was already sensitive and the motion of me rubbing against it was pushing her toward another orgasm. Realizing she was getting closer; I moved my dick back to her opening and readied myself for another attempt.

This time, I was able slide about half of my length into her pussy. Heather clamped her calves around my thighs, and I felt her fingernails dig into my chest. She let out a deep groan, then a full-fledged scream as she had her third orgasm within 15 minutes. (With only 50% of my dick penetrating in total!)

This time, I didn't give her any time to recover as I started thrusting in and out of her more aggressively. Her pussy was like a vice around my cock, the benefits of youth, I guess. It was soft, warm and flowing with juices though. Any guilt I felt about fucking someone 4 years my junior was quickly dispelled the longer I stayed inside her. With every thrust, I felt her pussy walls grip my cock, seemingly trying to milk it of its cum.

Within minutes, she achieved her goal as I felt my balls start to constrict and fill the condom with a load of sticky cum. I was covered in sweat and started to collapse on top of her, before realizing that I would crush her under my weight. I bridged up on my elbows, letting her breathe while she ran her hands over my back.

Not wanting any accidents, I slipped out of her, making sure the condom didn't lose any of its contents. I threw it out and returned to the bed where Heather was still recovering.

"What time is it?" she asked.

"Just after 10."

"Awesome. So, we have time for more! Can you go down and grab me a drink. I'm dying right now."

I threw some clothes back on and went back down the stairs to the pool, cooler, my roommates and a couple of remaining guests. By the smirks on their faces, it was pretty obvious that they knew what was going on. Being the mature 22-year-old that I was, I gave what I thought was the most appropriate response, a solid middle finger to all of them as I grabbed some drinks from the cooler.

They all laughed and as I turned to go back upstairs, my roommate Jim said, "Nice Shadow Puppets, by the way." Laughter filled the air as I turned back.

"What are you talking about?" Now, laughter erupted as John nodded up to my room.

"Check your lights next time .... Shadow puppets." I followed his gaze and realized that the couch we started fooling around on was up against the window of my room. Basically, we had given them a partial show through the closed blinds.

"You guys all suck" I said, which started yet another round of laughs as I climbed the stairs. When I got up to the room, Heather was sitting up in the bed (which at least confirmed our activities on the bed couldn't be seen from downstairs.)

"Oh no ... do they know we were fooling around up here?" Heather was blushing with embarrassment. "Were they laughing at me? What did they say?" I noticed she was trying to cover herself with the sheets as she spoke.

Despite Heather's flirtatiousness and aggressiveness at times, she was still only 18 and worried about being judged by a large group. I decided to spare her any further embarrassment, knowing that my idiot friends would never say anything about the "shadow puppets" to her, directly. They were jerks, but they weren't assholes.

I handed Heather a wine cooler and sat down next to her on the bed. "Yeah, I think they figured out what we're up to, but that's normal around here. We've all given each other crap when we bring a girl home. But they were mostly just giving me shit about why I wasn't gone longer!"

My white lie seemed to calm Heather down and we both drank the cold beverages as we lingered in the bed. Heather threw one leg over my hips and was laying on my shoulder. The distinct difference in temperature was actually erotic. Her cold hand, lips and breath from her drink felt great against my hot sweaty skin. My cock started stirring again and Heather felt it happening. We took a couple more sips and put our drinks back down before rolling toward each other to start kissing again. My bare cock pressed against her wet folds and for just a second I started to slip inside her.

Heather pulled back with a panicked, "Jay, we can't!"

"I know! Sorry. I literally slipped in! Let me grab a condom."

As I slipped into my second condom of the night, I saw Heather scrambling in the bed. When I looked over, she had positioned herself on her hands and knees, with her tan line-patterned ass up in the air.

"I've never done it like this, and I want to try."

I started moving toward her but then took a brief detour to turn off the main lights in the room. I turned on one lamp that gave the room a darker, sexier glow.

As I climbed up behind her, Heather asked, "Why did you turn off all the lights."

"A few reasons" I stammered. "First, it might help keep it cooler in here. Next, if I look at you bent over like that in full light, I won't last long. Finally, it's just sexier."

Heather seemed to accept my answer and wiggled her ass at me, "Well, then get over here and stick that dick back in me."

I did as she instructed and kneeled on the bed behind her. I shifted her legs a bit and told her to lean down on her elbows and pull a pillow under her head. While she did that, I reached down and grabbed my cock directing it into her pussy. This time, there was no resistance as she had opened up from our previous activities. Once I was comfortably in, I grabbed her hips and pushed forward.

"Unnnnnggghhhhh....holy fuck, Jason, that feels incredible." Heather again swirled her hips making circular motions around my embedded cock. I pulled back and thrusted again. Another groan escaped Heather's lips.

"Fuck, that's good. You feel so fucking deep. Do it harder...but not too much yet."

I started a slow but steady rhythm thrusting in and out of Heather's pussy. My fingers were digging into her hips where I had a solid grip on her thin frame. The room was filled with the scent of her arousal, and I could feel her juices dripping off my condom-covered cock onto my balls. Heather had her arms buried under the pillow with her head on top. She was grunting and moaning as I fucked her from behind. Thanks to the condom and our previous round of fucking, I was able to last much longer the second time.