Life is funny. Just when you think your ship is sinking and it is hopeless, a lifeline appears. My humiliating attempt to have sex with my teenage neighbor, Sharon, had resulted in a humiliating and dangerous premature ejaculation–dangerous because of the possibility of an unwanted pregnancy. And even though we dodged that bullet, I was too embarrassed by my performance to ask Sharon out again.
Of course, that was MY problem. Sharon probably felt that I had dumped her because we’d had sex, if you want to call it that, and the mystery was now gone from our relationship. She was “used goods.” I’d considered that might be going through her head, but I also couldn’t get over the thought that she might be telling anyone who would listen what a lousy lover I was who could only last for 60 seconds. In short, a laughingstock, albeit with a huge dick. Regardless, I was too embarrassed to actually talk to her and find out her true feelings.
But now, after my visit with Mrs. Collins, I was on cloud nine. I had performed well by all measures that I could think of (including the size of my cock…she actually measured it to be 10 inches when hard). At least it seemed that way once we started seeing each other on a regular basis thanks to my “job,” and it felt like this might be a regular thing. It looked to be a great summer: I had employment, sort of, and a guilt free fuck partner who was not only gorgeous, but also experienced and old enough that commitment was not even a consideration. This would be like sport fucking–or so I reasoned. I figured that I’d go off to college in the fall and return during holidays to resume where we left off. Keep in mind, however, this was the conclusion of an 18-year-old senior in high school whose idea of planning for the future was scraping enough change to buy 5 gallons of gas. As previously mentioned, my brain stem was lodged in my now measureably large cock.
But to paraphrase Bobby Burns, the best laid plans can easily go to shit.
My mother, despite her eternally positive demeanor, was not doing well. My good luck with Mrs. Collins was tempered by the fact that it would be a depressing summer with hospitalizations and eventually hospice for Mom. At that point, we all prepared for the inevitable. Mom seemed to handle it better than either Dad or I. She had carefully made all the necessary arrangements and seemed at peace with her situation.
“No one gets to leave this earth alive,” she reminded me. Her religious convictions also provided a sort of haven as well. She knew she was only going to a better place. I was not as convinced, but I held my tongue for a change and did my best to support her convictions.
And earlier than expected that summer she passed–peacefully, thanks to hospice and strong meds. We suffered through all the stages of grief and threw away tons of food, mostly nameless casseroles and a multitude of cheese trays, that was continually donated by friends and neighbors. By late-July we had resumed a normal life again, more or less.
My affair with Linda Collins continued, but with diminishing fanfare. Our family situation dampened things to the point where we occasionally had wild sex and let it all out, but for the first half of the summer much of my leisure time at her house was more like a counseling session. Linda was very sweet and let me bare my soul to her (and occasionally other things) while she listened and provided a shoulder to lean on. She became almost a mother to me, which seemed a bit incestuous in retrospect.
Sharon, my college aged neighbor who was the first to know me in the biblical sense, offered condolences as well, and we eventually did have what amounted to sympathy sex. She invited me over to her house when her parents were away on a trip, and we ended up in a tangle on her parents’ king-sized bed. As it turned out, I had misinterpreted her reaction to our misadventure in the front seat of my car.
We were in her living room on the couch, watching tv and drinking some of her parents’ wine, snuggling and doing lots of hugging. I let the sympathy card play out until I finally had to stop her.
“Look, Sharon. I truly appreciate your concerns, but I’m ok. I don’t mean to be ungrateful, and I am happy that you invited me over, but let’s talk about anything other than how I’m dealing with all these emotional issues. I do think about them, but I need a break from it. No disrespect to my mother whose memory I cherish. OK?”
“Oh, Sammie. I’m so sorry.” She looked at me with those teary, doe eyes waiting for what came next.
And with that, we were locked in an embrace, passionately kissing and groping. Her tongue explored my mouth, and we were like two snakes in heat. In no time I had Sharon’s sweater completely off, her bra on the floor and her slacks unzipped. Sharon held up her end by unzipping my fly, and after a considerable struggle, released my cock from the prison of my pants and began stroking it to a sizeable erection.
“God, Sammie, I think it’s even bigger than the last time I saw it. I’ve been thinking about your cock ever since that night, but I couldn’t tell myself it was as big as I thought it was. Here’s the proof. Please tell me you have a rubber this time.”
With a Cheshire grin, I looked up from sucking a pink puffy nipple, fumbled in my front pants pocket, and pulled out a sealed package containing a prophylactic. “Trojan Magnum at your service, ma’am. I’ll even let you put it on me.” I had purchased a dozen for Linda, but she was on the pill and preferred sex without any artificial obstacles. I had used a condom once with her, and we both agreed sex was better without it. But I knew better than to suggest that with Sharon.
“Wait, I want to try something before you put on that raincoat.” Sharon eyed me mischievously. “I want to see if I can fit you in my mouth.” And never taking her eyes off me, she lowered her head and stretched her lips to fit over the head of my cock.
My suspicions seemed to be confirmed. Sharon’s fellatio was incredible, possibly even better than Linda, although that would be a coin toss. After a few minutes of licking, kissing, and swallowing as much of me as she could muster, she looked up, gasping for air and breathing hard.
“Just don’t cum in my mouth. If you are going to cum, tell me! I’m a little weird about swallowing cum.”
“I promise.” I realized that after my first round with Sharon, my promises could be construed as empty. Apparently encouraged by my confidence, she hesitantly licked the underside of my glans and put the head back in her mouth. My stamina had improved appreciably, and I was pretty sure I could hold off for some time. But then when Sharon resumed her deliberations, I began to have my doubts. She licked and kissed my shaft like a pro, alternately sucking just the head and then forcing more of it until she gagged. Her fingers, unable to completely surround the shaft, worked like a slow moving piston in concert with her mouth. After a few minutes of lovemaking with my cock, she looked up. “Let’s get on my parents’ bed. This isn’t all that comfortable.”
Indeed, she was hunched over at an awkward angle of attack as I fondled her breasts and rubbed her pussy through her panties while she made love to my prick. She stood and stepped out of her slacks, naked except for a pair of thong panties. “C’mon, Sammie. Follow me.”
And I did, her perfect tits jiggling and her sweet ass swaying with each step.
The bedroom was an old-folks’ idea of comfort. Family photos adorned the dressers, and the bed was covered with shams and frumpy, decorative pillows. Sharon swept them to the floor with a couple of swift arm motions and directed me to the middle. My pants, boxers, socks, and shirt found the floor. I jumped into the center and rolled onto my back, my cock stiff and leaning slightly like a famous Italian tower, still glistening from Sharon’s fellatio.
“Should I remove my panties? I’ll be naked and embarrassed. Don’t look.”
All fake modesty aside, Sharon had the body of a goddess. Her firm cone-shaped tits sat like twin peaks on her chest, the nipples swollen and puffy. Years of gymnastics’ training had toned her to the point where her ass was as round and hard as an apple. Placing her thumbs on each side of her waistline, she swayed her ass and slid her panties slowly down in a mock strip tease, turning and showing me her perfect derriere as she looked over her shoulder, smiling. When she bent over to slip the panties off, she revealed pussy lips with just a smattering of pubic hair. She turned around and I could see that she was au naturelle–no shaved pudendum for her. She bore a tiny V of ginger colored pubic hair.
She jumped on the bed and kissed me on the mouth. Then she reached down and stroked my cock to ensure it was still at full mast.
“I think you’ve been practicing. I gave you my best blowjob and you are still standing, so to speak. A lesser man would have shot his wad by now.”
“I promise I’ll do better than the last time. I’m still embarrassed about it.” Her faith in my stamina to this point encouraged me.
“Accidents happen. Don’t worry about it. I’m just happy you remembered to bring protection. Let me see it.”
I handed her the package and she tore it open with her teeth. “Pre-lubricated…hmmm…I’m not sure it’s enough, but I know my mom keeps lube in her nightstand. I’ll need it or you’ll tear me apart with that baseball bat.”
She removed the wrapping and placed the rolled-up Trojan on the head of my cock, working it down with both hands. Even a “magnum” was a tight fit, but more importantly, it only covered half my length.
“Jesus, you need a custom fit, Sammie. At least it covers the important end. And I’m pretty sure it won’t slip off. It’s on there like second skin.”
Sharon reached into the drawer on her mother’s nightstand and after rummaging for a few seconds, yelled “Aha!” and pulled out a tube of Astroglide. She squeezed out a two-inch band into her hand and rubbed it over the end of my cock and around the lips of her vagina.
“I can’t even imagine my parents having sex, but I guess they do. It’s just weird to think about it. The proof is in the Astroglide.” Sharon kneeled and raised her ass above my member as she was talking, and grabbing it with her left hand, she sluiced it up and down her pussy lips before inserting just the tip in her vaginal opening. “Now let’s see if this bad boy will fit in me. I’ve been dreaming about this for weeks.”
I watched in awe as she ever so slowly lowered her ass onto my cock. She had a look of determination as her first effort met with resistance. My penis looked way too big for her, but Sharon persevered and succeeded in getting the head inserted.
“Holy shit, Sammie. I don’t know if I can take this. Your cock is so fucking big! I know it fit once before, but I’m too tight.”
The last thing I wanted was for her to give up. “Try some more lube. It’ll fit, I’m sure.”
She raised up and worked it back and forth with her hand to loosen her pussy lips before settling back down. Gradually her opening allowed the head and an inch or two in. She kept at it until she eventually had just over half of me buried in her.
“Unnngh,” she grunted as she held it there for a few seconds. “There! Mmmmm. God, it feels like a club is in me. But thank god for second efforts. I just need to start slowly to get used to you.” Sharon leaned forward and placed her hands on my chest for support as she carefully began to raise and lower her ass in small increments.
The table lamps provided enough light so that this time I had a great view of the action. Each time she sat up, her inner lips clung to my shaft, extending a good inch beyond her labia. The lube was doing its job, and she helped by reaching down and rubbing the excess around the union of my cock and her vagina. I resisted the temptation to thrust my hips, and I let her do all the work.
“Fuck, you are so fucking big. But it feels so good. How are you doing? Don’t cum yet, please. Just let me enjoy this for a while.” She bent down and kissed me. “I couldn’t get your big cock out of my mind, Sammie. I thought you hated me because you never called. Mmmm, right there. God, you are so deep. I think you’re almost completely in me.” Sharon had by now increased the length of her strokes until her ass made occasional contact with my thighs on a down stroke.
“I’m good. Your pussy is so tight, Sharon. You’re squeezing my cock like a vise.” As good as it felt, I was doing fine. Sharon was tighter than Linda, but now I knew how to maintain my composure and hold back. I began to thrust my hips into her as she settled on each downstroke.
“Not too deep, Sammie. It’s a little painful, but a good pain if that makes any sense. God, I’m so wet, I think I’m gonna cum soon.”
We gradually worked up a steady tempo and kept at that pace for about 10 minutes. I fondled her tits and played with her extended nipples. Sharon responded by bending and kissing me passionately. Eventually I was able to get nearly every inch of my cock in her. All that time Sharon was moaning and grunting in pleasure and issuing instructions. “Oh, yeah, right there, Sammie. God, that feels so good. You are so fucking big. I can’t believe how deep you are. I’ve never felt anything like this before. Oh, fuck, I’m going to cum soon. Don’t stop, please.”
I was squeezing her tits and alternately grabbing her ass to pull myself tighter into her, when she straightened up, screamed, and then bent down and buried her face in a pillow with a muffled, blood-curdling scream. I’m not sure what prompted me, but when she bent forward my hands were gripping each butt cheek, and without thinking, I inserted a lubed finger into her anus. Linda had done this to me once or twice and it made me shoot off like a canon.
Sharon had a similar reaction. She grabbed the sheets in clenched fists and screamed for all the neighbors to hear. She sat up enough to look me in the eyes and began slamming her ass onto my cock spasmodically while I wormed the tip of my finger in her ass. Her face was a combination of passion and determination.
“Cum in me, Sammie. Shoot your sticky cum in me.”
That was it. I grunted and shot a huge wad, thankfully into the end of my magnum. Sharon continued grinding her ass into me until we both finally stopped jerking and throbbing. When she slipped off me, her pussy was red and swollen. The rubber on the end of my cock was filled with gooey semen. Her voice was shaky.
“Fuck, Sammie. That was wild. I’ve never had an orgasm like that. Jesus, I thought I was dying for a second. And then when you stuck a finger in my ass, Holy Shit! Where did you learn to do that?” We were both drenched in sweat. Sharon cuddled up to me–smashing her tits in my chest and kissed me.
“You’ve definitely been practicing. I don’t know how or with whom, but that was fucking awesome. Maybe it was just fucking in my parent’s big bed…way better than the front seat of your car! I don’t know.”
No way was I giving up any secrets. “No. It’s just you,” I lied. “You bring out the best in me.” Even though I still had Linda to plow, I greedily decided two pussies are better than one. How could this possibly go wrong? I was living a fantasy despite the sadness and depression of losing my mother.
We lay there for 15 minutes or so, kissing and fondling. Feeling another urge, I rolled on top of Sharon and got on my knees between her legs. I tried to insert my stiffening cock in her again, but she put a hand on my chest.
“No way, Buster. I’m going to be sore enough as it is. You’re going to need to break me in slowly. My folks are going to our cabin most likely after they return from their trip. The house will be empty. In the meantime–here, take these.” She grabbed her panties and wrapped them around my cock. Jack-off with these if you need to. They’ll remind you of me. And I’ll be dreaming about your one-eyed friend here.” She placed two fingers on her lips and transferred a kiss to my cock, giggling.
We returned to the living room and watched tv listlessly before I excused myself and headed home after kissing Sharon good-bye. Maybe this summer might not be so bad after all.