Before my dad remarried and I entered college, life had been a series of ups and downs. Mom was diagnosed with cancer when I was a freshman in high school, and she finally succumbed to the disease the summer after my senior year after a long, drawn-out battle with both chemo and radiation treatments. She hung in there until the bitter end, but her last days were an emotional roller coaster for dad and me as we both secretly knew the end was in sight but refused to admit it to one another or ourselves.During my high school years, her condition affected me in a variety of ways. I tended to engage in risky behaviors and got in a fair amount of trouble at school. Of course, this didn’t help our home life. The last thing my parents needed was to worry about me, but it was my way of rebelling to circumstances beyond my control and mom’s spiraling health issues.My friends typically avoided the subject of my home life, and I went through a few typical high school romances that tended to be short-lived, mainly because of my bad attitude. I dated a few very sweet girls who tried valiantly to change my bad boy ways and a couple who got a thrill out of my negative behaviors and troublemaking.Most of the time, I was in a relationship for self-gratification. The one thing my girlfriends had in common was a particular look. Personalities came secondary. Anyone with a brain could see that I liked big tits, and my dates fit that body profile almost always. My brain was in my groin as I was repeatedly reminded by my friends.At the age of eighteen, I lost my virginity to an older neighbor girl who was a freshman at a nearby community college. I can’t say it was a particularly wonderful experience since it took place on the uncomfortable bench seat of my ancient Chevy Bel Air after we had been dating for about a month. One night when her parents were out for dinner, I reached second base with her in her living room by successfully getting her bra off and fondling those perky teenage tits, but she stopped me before I could get into her panties for fear her parents would walk in the door during our wrestling. She did offer hope for future entanglements, however, if we could find a place of privacy.”Not here, Sammy. What if my parents walked in on us? I’d be grounded for the rest of my life!”Of course, my house was off-limits since my bedroom was next to my parents and my ailing mother was always home.That prompted an area search, and many miles and a tank of gas later I discovered a hidden parking place with a view of city lights. And so, after a movie and a few hits off a joint I’d been saving, we drove to my magical spot to check out the view. In no time, we were entangled in a heavy make-out session and after an appropriate amount of kissing and light touching, I moved in for the next stage of my plan.Even though the heater in my car barely worked, I successfully convinced Sharon that this would be a romantic culmination of our relationship as I grappled with first her jacket, and then her sweater. After a few minutes of serious fondling underneath that garment, I had eventually worked it up above her bra and convinced her it would be better removed. With no help from her, I eventually got her bra unclasped and the pleasures of bare breasts awaited me. Immediately my lips found a large pink nipple and attacked it with gusto. With Sharon’s eventual encouragement and instructions, I made a meal of her ripe teenage tits.My success with her perky cone-shaped breasts only emboldened me further, and I was soon able to work a hand under her skirt and inside her panties without any objection, eventually slipping a finger into her juicy vagina. This caused even greater gasps of pleasure as both of us ignored the cold vinyl seats and the occasional pokes from the floor shifter. I had rounded third base and was headed for home. With a free hand, I had sneakily unfastened and lowered my pants and boxers to my knees, and in the dim evening light, Sharon got a glimpse of my rock-hard boner for the first time. She gasped, but this time in shock.”Oh…My…God!”I just happen to be blessed with a rather large cock, and when it is angry, it swells in girth as well as length, prodigiously so. This is something I proudly achieved on a regular basis while locked in my bedroom late at night with an ancient and well-used Penthouse publication in front of me and a box of tissues on the nightstand. One other girl had previously seen my penis and decided then and there that I was a freak and would have nothing further to do with me or my appendage. Her negative reaction did not exactly boost my ego. It had the opposite effect, and I honestly began to think I was a freak of nature and would remain a virgin for the rest of my celibate life.So, when Sharon caught a glimpse of my virginal penis, she practically fainted. “Jesus, Sammy. You are huge. I don’t think that thing will fit in me!”Despite her reservations and after much encouragement from me and giggling from her, Sharon tentatively wrapped her hand around my swollen member and stroked it–almost too professionally for a nineteen-year-old whom I always thought was sweet and innocent. I was doing my best to strategically place myself between her legs on the narrow car seat, carefully avoiding the Hurst floorboard shifter, and kneeling in a position to finally experience actual fornication. And with her help and even more giggling, I soon found Valhalla as she finally succeeded to get just the head of my cock between the unshaven lips Escort of her pussy.”Oh, my god. I’ve never seen a cock this big. You have just the tip in me, and I feel stuffed!”This both pleased and disturbed me. Clearly, Sharon was impressed by my penis, but then it sounded like she had been here many times before, obviously with guys other than me. I guessed she wasn’t a virgin. My disappointment was short-lived, however, overridden by the fact that I was about to get rid of that label for myself.In short, I just wanted to fuck her, and her soft pussy flesh felt nothing like my own calloused fist. After some mutual groaning and pleas from Sharon to not cum in her since I didn’t come prepared with a rubber, I began working more than just the bulbous head of my cock inside her. Sharon was biting her lip as we both watched inch after inch of my thick shaft disappear into her velvety vagina.”Oh shit, Sammy. God, your cock is so fucking big. Jesus, whatever you do, don’t cum in me. I’m not on the pill.”Her hand was on my stomach as a precaution to my exuberance. She craned her neck and gasped each time I pushed inside her, fucking her ever so slowly at first and then gradually increasing my tempo as my excitement grew. And my excitement was growing quickly, as was the too-soon urge to empty my balls.Sharon looked up at me and just managed to get out a compliment that put me over the edge,”God, Sammy, your cock is splitting me in two! I can’t believe how thick you are. You feel so good in me…” when suddenly, approximately two minutes after insertion, I groaned loudly and exploded with a huge burst of cum inside her.Sharon’s demeanor quickly turned from passion to panic. It only took a second or two for her to realize that I was pumping a steady stream of semen into her warm and willing pussy.”Oh, shit! What are you doing, Sammy? I told you not to cum in me. Jesus, and so soon! I was just getting warmed up!”I hurriedly pulled out–obviously too late–as my cock continued to squirt sperm over her stomach and onto her jutting tits now exposed by the loosened bra incongruously wrapped around her neck.”Sorry,” I muttered. “I didn’t mean to cum so fast. But I don’t think I got much inside you.” As if that mattered. Besides, it was a lie. A river of white, sticky cum began draining out of her pussy trailing the sudden withdrawal of my softening member. My rapidly shrinking organ continued to leak the final remnants of my pent-up product onto her stomach and down onto the cold vinyl seats of my Bel Air.We quickly cleaned up as best we could, using my t-shirt as a cleaning rag, and Sharon asked me to take her home so she could try some home remedies to avoid an unwanted pregnancy. That effectively ended the romance for a while as we both feared the worst. Eventually, though, we realized we had dodged a bullet and none of my soldiers had found a home during the invasion of her pussy. But even so, between the embarrassment of my premature ejaculation and tempting fate with an unwanted pregnancy, I deliberately avoided Sharon.So, my first experience, while pleasurable for me at least, was so short-lived that it only encouraged me to practice more. Unfortunately, my practice sessions were done solo. I was humiliated by my performance with Sharon, and I don’t think she was too impressed with my stamina despite the pleasing size of my tool in her view. So, by mutual agreement, our relationship seemed to dissolve after that. I did fantasize about those fabulous breasts of hers and the sight of my cock being guided by her encouraging hand into her waiting pussy. In my fantasies, though, I lasted much longer until she was begging me to stop. But instead of coming in her tight pussy, I filled a handful of Kleenex tissues.Mom was not doing well during this time, and we had lots of well-wishers and friends who offered help in a variety of ways. One spring day on my way home from school, I ran into a neighbor lady down the block who had befriended mom, and she inquired how things were going. I was walking by her house, and she was watering some flowers along the sidewalk in a tight pair of shorts and a tank top that caught my attention. I thought it was someone much younger until she turned around in surprise when she heard my footsteps, and then gave me a big smile.”Oh, hi! You startled me! How’s everything, Sammy? I haven’t talked to your mom in a while. How’s she doing?”Like most folks, Mrs. Collins’ inquiries tended to be generic so as not to seem intrusive. The handwriting was on the wall as to the probable outcome, but everyone just wanted us to know they cared about what we were going through as a family.”Oh, you know. Some good days and some bad. Thanks for asking.” Mrs. Collins had always been nice to me, and I had secretly fantasized about her in a far-fetched dream after realizing during one of my visits to mom that she had great tits. She was very attractive to me, even as a middle-aged friend of my mother. But I also figured it was probably weird to be attracted to an older woman.”How about with you? Do you have a job lined up for the summer?”“No. Nothing yet. But I really haven’t been looking much since school is still going on.””You know, Sammy, if you have some time, I could use a little help with some yard chores, and I’d pay you well. It’s hard to find help these days and since I’m single, there’s a few things I can’t do very easily. Are you interested? Nothing too difficult for a big, strong guy like you but hard for me. I’m afraid I’m Escort Bayan not very handy when it comes to house maintenance.”Mrs. Collins was petite…maybe 5’5″ and thin except for her big boobs. She was clearly fit, and I frequently saw her running to stay in shape. I assumed she had to wear a running bra, but even then, her breasts appeared to be quite large as they bounced deliciously. In a tank top, they were hard not to notice.Since I was without two nickels to rub together, and gas money did not come easily, I jumped at her offer but tried to sound nonchalant. “Sure, I can help out, and I do need some gas money for my jalopy. Seems like I’m always running on empty.””Well, your car does look a little worn I’ve noticed, but you seem to be in good shape. You must work out!” She reached up and gave my biceps a brief playful squeeze. “Mmmm, I bet the girls are breaking your door down.” She winked and smiled at her comment.Obviously, she was joking with her flirtations, but I certainly didn’t mind. Mrs. Collins could still turn heads. More than once, I saw my dad staring greedily at her when she was visiting mom. One time I overheard him say to a friend something about how much fun it would be to get her in the sack. She had a reputation after she moved into the neighborhood as being promiscuous, but it was likely wishful thinking from gossipy neighbors who were probably jealous of her obvious good looks and attention from the men of the neighborhood. She was single and the word on the street was she was divorced from her shithead husband before moving here.Red-faced, I pulled my shoulders back and sucked in my stomach in response to her compliment. I had to force myself to look at her face and not her chest, which begged for my attention. “Actually, I can probably stop by tomorrow if that’s ok. I don’t think I have anything going on after school. Football practices are done for the year.””Well, the weather’s nice now, so feel free to stop by any day. If my car is in the driveway, I’m home. I live the life of a spinster these days. Having a young man to talk to would be a welcome addition to my boring life. Anytime, even evenings if that works better for you. We can discuss what needs to be done and compensation for you.””Ok, thanks. Sounds good.””Nice seeing you, Sammie. Say hi to your mom. I need to get over there and see her.”She turned and walked back down the street toward her house, and I stood there, following her with my eyes until she turned her head and saw me staring. She gave me a little wave and a giggle as she turned up her driveway. I could see what my dad saw in her at that moment. Mrs. Collins was still a babe, or a MILF as my friends would say.The next day I got home from school and took a shower. I had showered that morning, but I wanted to be fresh after a day in stuffy classrooms. I combed my hair, put on a tight t-shirt to accentuate my chest and arms, and even a dab of cologne. I posed in front of my bedroom mirror. My 6’1″ reflection looked pretty good, I reasoned. I stuck my head in the bedroom where mom was resting and said I’d be back soon.”Where’re you headed? You look like you’re going on a date to see a bodybuilder!””I’m looking into a job opportunity. I’ll tell you later.””Well, good luck then. But I think a nice shirt would be more appropriate for a job interview, don’t you? That t-shirt is pretty tight.””No, this is for physical work. I need to show off my guns.” I smiled and waved goodbye. “See you soon.””Good luck, then. Don’t be too long. Dinner’s at six or shortly after.”I practically ran down the street and in minutes I was in front of the Collins’ house. Her red Mustang sat in the driveway. I took a deep breath and walked up to the front door and rang the bell. I waited a few seconds with no result and then rang it again.After a moment or two, I heard footsteps padding on the tile floors and the door unlock. Mrs. Collins opened it cautiously at first until she saw who it was and opened it the rest of the way.”Oh, Sammy. Nice to see you again. Come on in. I’m afraid I’m a bit of a mess…I just got out of the shower and my hair is wet, but you look nice. And you smell good too. I love that cologne.”She was wearing a thin knee-length summer robe, and I tried not to stare but her nipples jutted prominently through the material. She tightened it and retied the waist strap which accentuated her breasts even more. She gave me a hug and briefly pressed her bosom into me. “I forgot you said you’d be over today.” Her thick blonde hair was hanging still damp as she pulled it into a ponytail and secured it with a rubber band. I tried not to stare at her boobs as they jiggled with the action of her arms.”I can come back if this is a bad time, Mrs. Collins. You said anytime and your car is in the driveway.” I placed my hands in front of me. I could feel my shorts starting to tent at the sight of those prominent nipples.”Oh, no. This is fine, Sweetie. I just need to slip on some clothes, so I look presentable. Sit down and make yourself comfortable. Before I change, can I get you something to drink? Water? A beer? Oh, sorry. You’re too young, I guess. But I’m having a glass of wine. If you’d like a beer, I won’t tell.””Uh, water’s fine, thanks.” The fact that Mrs. Collins had offered me a beer made me feel like an adult, but I didn’t need to go home with beer on my breath.”I’ll be back in a jiffy.” She disappeared to the kitchen and returned shortly with a tall glass of iced water and a glass of Bayan Escort red wine. Her breasts jiggled tantalizingly with each step as she marched across the living room and stood in front of me with the beverages. Oddly, I noticed that she was now wearing bright red lipstick and assumed she had applied it when she left the room.She leaned forward to set the water down, and her robe opened just enough to offer a tantalizing peek of a ripe globe capped with a prominent pink nipple. She leaned back and adjusted the robe self-consciously when she realized it had opened.”Sorry about that. No one wants to see an old lady’s boobs, especially a young man who probably has his pick of young, perky ones.” She giggled and self-consciously tried to close her robe even tighter. “Mine used to be that way but gravity is a son-of-a-bitch.”Her frankness took me by surprise, but not wanting to seem prudish, I tried to look serious and reassuringly mature about a woman’s breasts.”Your boobs are nice, Mrs. Collins. I mean… I’m sorry. I don’t mean to be forward, but you have nice boobs. I’m sure,” I added quickly as if I hadn’t been gawking at them. I was, no doubt, beet-red at this point. I fumbled for the right thing to say, and I tried to smile through my embarrassment, but at the same time, my cock was getting uncomfortably stiffer by the second.”Well, first, let’s drop the Mrs. Collins stuff.” She sat next to me on the couch at an angle, her knees touching mine and her hands folded in her lap. “That’s way too formal. Just call me Linda. And thank you. No one has complimented my old boobs in ages…or any part of me for that matter. It IS nice to be noticed. She took a sip of wine and sat upright, pulling her shoulders back just a fraction.”I do try to stay in shape as gravity takes its course. Not too bad for forty, although you should have seen me when I was in high school. I was very popular with the boys. But those days are long gone. As you probably know, my husband left me for a younger version a few years ago and it’s been a long dry spell, not to mention lonely. Being a divorced woman has its drawbacks. You’re the first man to pay me a compliment in some time…although I suppose I don’t get out much anymore to receive any notice, and most of the women are protective of their men around a divorcee. Too much information, I know. I exercise regularly, but mother nature and age can be cruel. Thanks anyway, Sammy. You’re a sweetie.””You’re very attractive, Mrs. Collins. I hear lots of people say that about you.””Oh, Sammy, thank you. That’s a sweet thing to say. You’re so nice. And handsome too! I’d jump on you if I were younger!”And with that, she reached over and placing a hand on my knee, planted a motherly kiss on my cheek.”Older women love to hear compliments, even if they are forced.”I turned to her, a look of confusion on my face, not knowing what to say or do…and then I kissed her back, awkwardly, and not on the cheek. Something just came over me, and I reacted. The smile on her face turned to surprise when I reached around her with my arm and kissed her. As my lips touched hers, she jumped a bit, but then she relaxed and opened her mouth. Suddenly, I felt a wet tongue tangling with mine. I pulled her closer to me, and we stayed that way for several seconds…but it felt like an eternity. My cock responded appropriately. Finally, she pushed me a few inches away and looked me in the eyes. Her pale blue eyes seemed to be pleading.”Whew! I think I started the wine a bit too soon today, Sammy! I’m not sure what has got into me but thank you for taking pity on an old lady. It’s not every day a handsome young man compliments me, let alone kisses me. You definitely got my blood moving.” She smiled and gave me a peck on the lips as if to say, “that was nice, but we’d better stop here.””Mrs. Collins…umm, Linda,” I stammered. “I’m so sorry, but you are so sexy, and I couldn’t resist. I apologize if I’m way out of line here. I didn’t mean to offend you. I’m sorry your husband left you…and… It’s just…well…I couldn’t help myself. You are very attractive and… hell, I don’t know what to say. I’m sorry.””Oh, honey. No offense taken.” We were still inches from one another, and I could smell the wine on her breath mingled with fresh bath scents. She patted my knee and let her hand run along my inner thigh as if to ease my embarrassment. Suddenly she started, and her face changed to a look of surprise. Her hand found the end of my cock nearly extending out the leg of my shorts and she slid her hand lightly up and down its length, squeezing it along the way. Her surprise soon became a smile.”Oh my god! What have we here? Oh, Sammy. Is this all you, Sweetheart? Am I dreaming?” She looked down at the bulge in my shorts. “Did I do this to you?””Sorry,” I apologized. “It has a mind of its own. I can’t help it. It’s embarrassing.” I tried to push my legs together to hide my huge erection but the restriction in my shorts prevented my knees from going together.”Sweetie, you have nothing to be embarrassed about. This is the nicest gesture anyone has made at me in ages. And on top of that, that’s quite a whopper you have going there. I’m flattered if I can do this to someone your age. I’m a proud woman who doesn’t get much attention anymore. Don’t try to hide it. Please! You might hurt yourself.”She giggled and then we both sat there in silence for a pregnant moment. Finally, I sheepishly opened my knees and smiled as if to say, “What the hell.” With a look of amazement on her face, Linda looked down and put both hands on the tubular shape and gave it a gentle squeeze. Then, she looked directly at me with penetrating animal eyes. Suddenly, she leaned over and kissed me tenderly on the mouth.