Life is funny. Just when you think your ship is sinking and it is hopeless, a lifeline appears. My inept 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 likely thought I felt she was now "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; someone who could only last for sixty seconds. In short, a laughingstock, albeit with a huge dick. Regardless, I was too embarrassed to talk to her and find out her true feelings.

But now, after my visit with middle-aged 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 measured it with a tailor’s tape to be ten inches long and a whopping eight inches in circumference when hard). At least it seemed that way once we started seeing each other regularly 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 eighteen-year-old senior in high school whose idea of planning for the future was scraping enough change to buy five gallons of gas. As previously mentioned, my brain stem was lodged in my verifiably 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 me. 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 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 despite my skepticism.

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 were continually donated by friends and neighbors. By late July we had resumed a normal life again.

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 their 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 all this. No disrespect to my mother whose memory I cherish. OK?"

"Oh, Sammy. 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 sizable erection.

"God, Sammy, I think it's even bigger than the last time I saw it," she gasped as my thick penis continued to grow in her small hand. "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 condom this time."

With a Cheshire grin, I looked up from nibbling on 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 Mrs. Collins, 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 Mrs. Collins, 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 in the front seat of my car, my promises could be construed as empty. Encouraged by my confident oath to restrain my sperm, she hesitantly licked the underside of my glans and put the head back in her mouth, eyeing me warily before returning to full concentration on the task at hand. My stamina had improved appreciably with Mrs. Collins, and I was pretty sure I could hold off for some time with Sharon. But then when she 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 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 and struggled for air. "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 perky 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, Sam. Follow me."

And I did, her perfect cones 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 nineteen-year-old goddess. Her firm torpedo-shaped tits sat like twin peaks on her chest, the large pink 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 away 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 downy pubic hair. She turned around and I could see that she was untrimmed--no shaved pudendum for her. She bore a tiny V of ginger-colored pubic hair. My memory of her pussy in the darkened front seat of my car had faded, but in the full light of her parents' bedroom, I realized it was a thing of beauty. Her labia were not as large as Mrs. Collins, but her clitoris was huge.

She jumped on the bed and kissed me. Then she reached down and stroked my cock to ensure it was still at full mast.

"I think you've been practicing, Sam. I gave you my best blowjob and you are still standing, so to speak. A lesser man would have shot his wad by now." As she spoke, she kissed and licked just the glans, and even inserted the tip of her tongue into my piss hole. I was only slightly disappointed by her revelations about the quality of her fellatio. Sharon was proud of her skills.

"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 condom, and she held it up for inspection before she tore open the packaging with her teeth.

"Jesus, this thing is huge. And pre-lubricated! Hmmm...I'm not sure it's enough, but I know my mom keeps lube in the drawer of her nightstand. I'll need it or you'll tear me apart with this 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, Sammy. At least it covers the important end. And I'm pretty sure it won't slip off. It's on there like a 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. Her "little man in the boat" glistened as she applied the lube liberally to her labia and clitoris.

"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 lube." Sharon kneeled and straddled me, her ass hovering above my member as she was talking. She grabbed it with her left hand and sluiced it up and down her pussy lips before inserting just the tip between her well-lubricated labia.

"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 and the glans flattened against the opening to Valhalla. She took on a look of determination as her first effort met with resistance, and my cock slipped up and over her clit. My penis looked way too big for her, but Sharon persevered and succeeded in finally getting the tip inserted. She settled carefully on it until the plum-sized glans had disappeared into her cunt.

"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. I've got just the head in, and I feel stuffed!"

The last thing I wanted was for her to give up. "Try some more lube. It'll fit, I'm sure."

She raised her ass and worked it back and forth with her hand to loosen her pussy lips before settling back down again. Gradually her opening allowed the head in plus an inch or two. She kept at it until she eventually had just over half of me buried in her.

"Holy shit," 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 either side of my chest for support as she carefully began to raise and lower her ass in tiny increments, wiggling from side to side to ease the penetration. Her nipples grazed my chest as she maneuvered her body for a comfortable position.

"Oh fuck, your cock is so fucking big, Sammy. But look, I almost have all of it in me! Jesus, it feels like I'm sitting on a pole." Sharon's neck was bent sharply so she could watch as my prick disappeared in her.

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 most of the work. I reached up and rubbed her clitoris with my thumb as we fucked, eliciting moans and grunts of pleasure through closed eyes.

"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 and then whispered in my ear, "I couldn't get your big cock out of my mind, Sammy. I thought you hated me because you never called. Mmmm, right there. God, you are soooo deep. No one has been that deep before...I'm a virgin there. You feel wonderful, but I'm going to be sore tomorrow." Sharon had by now increased the length of her strokes until her ass made occasional contact with my thighs on a downstroke.

"I'm good, Sharon. Your pussy is so tight. You're squeezing my cock like a vise." As good as it felt, I was doing fine and able to hold off my inevitable explosion of cum. 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 into a steady rhythm with her ass.

"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 going to cum soon."

We gradually worked up a steady tempo and kept at that pace for about ten minutes. I fondled her tits and played with her extended nipples. Sharon responded by bending and kissing me passionately while she ground her ass in tight circles, something that Mrs. Collins liked to do as well. Eventually, I was able to get nearly every inch of my cock in her with each upstroke. All that time Sharon was moaning and grunting in pleasure and issuing instructions.

"Oh, yeah, right there, Sammy. 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. Just a little longer. I'm getting close."

I was squeezing her tits and alternately grabbing her ass to pull myself tighter into her when she straightened up and let out a guttural moan. She then bent down and buried her face in a pillow with a muffled, blood-curdling scream. My fingers were well lubed as I occasionally wrapped them around my shaft to smear any excess on her labia. I'm not sure what prompted me, but when she bent forward my hands were gripping each butt cheek, and without thinking, I found her anus and inserted the tip of my lubed finger into that orifice. Linda had done this to me once or twice and it made me shoot off like a cannon.

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 twisting 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. By now my finger was deep enough to feel the thick shaft of my cock through her perineum. Sharon bent forward to give me freer access to her ass, her tits grinding into me.

"Cum in me, Sammie. Shoot your sticky cum in me. I want to feel your big cock pulsing inside my pussy. It's ok--the rubber will protect me. Let me have it. God, you made me cum so hard!"

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 still firmly attached and filled with gooey semen. Sharon's 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 now drenched in sweat. Sharon cuddled up to me--smashing her breasts into my chest--and then kissed my lips and all over my face in appreciation.

"Thank you for that, Sammy. You've 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. But whatever you've been doing, keep it up."

No way was I giving up any secrets.

"No. It's just you," I lied. "You bring out the best in me. And a comfortable bed didn't hurt. Maybe I should get your parents a thank-you card."

Sharon giggled and kissed me again.

Even though I still had Mrs. Collins to plow regularly, 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. At least fucking took my mind off all the terrible shit I'd been dealing with. The fact that I had my choice between a tight-bodied teenager and a voluptuous middle age MILF was almost too much to comprehend.

We lay there for fifteen minutes or so, kissing and fondling. Finally, Sharon sat up and slid the condom off my softened prick, gingerly holding it by the open end and examining the quantity of sperm pooling in the tip.

"My god, Sammy. Thank God for rubbers. It looks like there's a quart of cum in this thing. Happily, it is contained inside it. I didn't know they made rubbers this big, but I'm glad they do." She carefully placed it on some tissues on the nightstand.

Feeling another urge, I rolled on top of Sharon and got on my knees between her legs. I reached for another condom and was about to put it on my cock for round two, 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.

We returned to the living room and, snuggling, watched tv listlessly before I eventually excused myself and headed home after kissing Sharon goodbye. Maybe this summer might not be so bad after all.