Sammie, the Early Years Ch. 01

Anal

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 during the summer of 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 trouble making.

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 18 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 as 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.

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. Even though the heater in my car didn’t work, I successfully convinced her this would be a romantic culmination of our relationship as I grappled with first her jacket, and then her blouse. After a few minutes of serious making out, I had worked the clasps of her bra loose and after pulling open her blouse, my lips found a large pink nipple. With Sharon’s encouragement, I made a meal on her ripe tits. Soon, I was able to slip a hand under her skirt and inside her panties, eventually getting a finger into her vagina. This caused even greater gasps of pleasure. Then, when my pants and boxers came down to my knees and she saw my rock-hard boner, she gasped again, but this time in awe.

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.

So when Sharon caught a glimpse of my virginal penis, she practically fainted. “Jesus, Sammie. You are huge. I don’t think that thing will fit in me!”

Despite her reservations, Sharon wrapped her hand around my swollen member and stroked it–almost too professionally for a 19-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, avoiding the Hurst floorboard shifter, and get in a position to finally experience actual fornication. And with her help and a bit of giggling, I soon found Valhalla as she finally was able to insert just the head of my cock between the hairy lips of her pussy.

“Oh my god. I’ve never seen a cock this big.”

This both pleased and disturbed me. Sharon clearly 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.

But at that moment, I just wanted to fuck her, and her pussy felt nothing like my own 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 head inside her, fucking her slowly at first and then rapidly. Sharon stared in disbelief as my huge member stretched her pussy. She moaned in pleasure and managed to just get out, “God, Sammie, your cock is splitting me in two!” when suddenly, approximately 60 seconds later I groaned loudly and exploded with a huge burst of cum inside her.

“Oh, shit! What did you do? I told you not to cum in me, Sammie. Jesus, and so soon! I was just bonus veren siteler getting warmed up!”

I hurriedly pulled out–too late as my cock continued to squirt hot jizz over her stomach and onto her jutting tits now exposed by the loosened bra. “Sorry,” I mustered. “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 vagina trailing the sudden withdrawal of my member.

We quickly cleaned up as best we could, and Sharon asked me to take her home so she could try some home remedies in an effort 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.

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 invariably 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. So, by mutual agreement, more or less, our relationship seemed to dissolve after that. I did fantasize about those fabulous breasts and the sight of my cock being guided by her hand into her waiting pussy. In my fantasies, though, I lasted much longer until she was begging me to stop. 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 and gave me a big smile.

“Oh, hi! You startled me! How’s everything, Sammie? 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.

“Oh, you know. Some good days and some bad. Thanks for asking.”

“How about with you? Do you have a job lined up for the summer?”

“Naw. Nothing yet. But I really haven’t been looking much since school is still going on.”

“You know, Sammie, 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 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.

Since I was broke, and gas money did not come easily, I jumped at the chance. “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 over and gave my biceps a brief playful squeeze. “Mmmm, I bet the girls are breaking your door down.”

Obviously, she was joking with her flirtations, but I certainly didn’t mind. Mrs. Collins was attractive and even though she was a friend of my mother, she 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.

Red-faced, I unconsciously pulled my shoulders back in response to her compliment. I forced 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 followed her with my eyes until she turned her head and bedava bahis 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 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 stuck my head in 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 body builder!”

“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.”

“Naw, this is for physical work. I need to show off my guns.” I smiled and waved good-bye. “See ya 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.

After a few seconds 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 then opened it the rest of the way.

“Oh, Sammie. 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 summer knee length robe, and I tried not to stare but her nipples prominently jutted through the material. She tightened it and tied the waist strap which only accentuated her breasts even more. She gave me a hug and pressed her bosom into me. “I forgot you said you’d be over today.” Her blonde hair was hanging, still wet, as she pulled it into a pony tail and secured it with a rubber band.

“I can come back if this is a bad time. You said anytime and your car is in the driveway.” I placed my hands in front of me as my shorts started to tent at the sight of her pointy nipples.

“Oh, no. This is fine, Sweety. I just need to slip on some clothes real quick. 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 jiff.” She disappeared to the kitchen and returned shortly with a tall glass of ice water and a glass of red wine. Her breasts jiggled tantalizingly with their thin covering as she marched across the living room and sat next to me on the couch. She leaned forward to set the water in front of me, and her robe opened just enough to offer a peek of the inside 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 stud who probably has his pick of young, perky ones. Mine used to be that way but gravity is a son-of-a-bitch.”

“Your boobs are nice, Mrs. Collins. I mean…, I’m sorry. I don’t mean to stare, 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 as I fumbled for the right thing to say. I tried to smile through my embarrassment, but at the same time my cock was getting uncomfortably harder by the second.

“Well, first, lets drop the Mrs. Collins stuff. That’s way too formal. Just call me Linda. And thank you. No one has complimented my boobs in ages, or any part of me for that matter. It IS nice to be noticed. She took a sip of wine and thrust her chest out. “Not bad for 40, though. You should have seen these babies when I was in high school. I was very popular with the boys. But 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. You’re the first man to pay me a compliment in some time…although I ‘spose I don’t get out much anymore to receive any notice. I do try to stay in shape, but mother nature and age can be cruel. Thanks anyway, Sammie. You’re a sweety. 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 kiss on my cheek.

I turned to her, a look of confusion on my face, not knowing what to say or do…and then I returned her kiss, awkwardly, but 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 deneme bonus arm and kissed her. As my lips touched hers, she jumped a bit, but then she opened her mouth and a wet tongue tangled with mine. Our arms went around one another, and we kissed passionately and long…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.

“I think I started the wine a bit too soon today, Sammie. 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…along with some other juices.” She smiled and gave me a peck on the lips.

“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. 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. 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 up and down its length, squeezing it along the way.

“What have we here? Oh, Sammie. 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 is embarrassing.” I tried to push my legs together to hide my huge erection.

“Sweety, you have nothing to be embarrassed about. This is the nicest gesture anyone has made at me in ages. And to top it that, that’s quite a whopper you have going there. If I can do this to someone your age, I’m a proud woman. Don’t try to hide it, please.”

I opened my knees and Linda put both hands on the tubular shape running down my leg. She looked me in the eye and kissed me, open mouthed before once again pleading with her eyes.

“Sammie, stand up for a minute.”

I did as I was told as she turned me to face her on the couch. Looking directly into my eyes, Linda gently unbuckled my belt and undid the button at the waist. My shorts were a bit on the loose side at the waist, and she easily unzipped them. She reached under my t-shirt and grabbing my shorts and my boxers at the same time, slowly lowered them until, finally, when they were just above my knees, my cock sprang out like a Jack-in-the-box.

“Oh, my lord. It is all you. Jesus, Sammie. You are packing some serious heat here.” She reached up with both hands and placed them on my cock. Her fingers did not completely enclose it as she slid them slowly up and down its length. Her voice suddenly changed as if she were in a daze, and she stared at the swollen head with a look of amazement. “Sammie, you have a gorgeous cock, and so big and fat.” She examined it, smiling and licking her lips. “Would you mind if I put it in my mouth. Would you care if an old lady gave you a sloppy, wet, blowjob? Hmmm? I used to be pretty good at this.”

She looked at me with puppy eyes and kissed the plum sized head.

“Uhh, sure, I guess. If you want to.” I had never had a blowjob before, and I couldn’t believe my ears. This beautiful 40-year-old woman was about to put her lips around my prick. I was stunned. Nothing had prepared me for this moment. “Mrs. Collins…umm…Linda. Do you mind…umm…can I see your tits.” As the words came out of my mouth, I realized how stupid they sounded.

“Oh, Sammie. You can not only see them. You can squeeze them and suck on them, honey. But first, let’s see if I can fit this bad boy into my little mouth.” She dropped her arms momentarily to shrug off her robe after first untying it, and it fell to the couch exposing two beautiful breasts capped with dollar sized areola and pencil erasure nipples. Her breasts sagged a bit, but her nipples seemed to defy gravity and point slightly upward. “Go ahead and squeeze them, honey, while I suck your cock.” And with that, she opened wide and wrapped her lips around the head of my cock. As she sucked, her tongue periodically came out and licked around the circumcised head until it glistened with her saliva. She worked both hands up and down, occasionally letting one drop to caress my balls.

I fondled her big tits, pinching and pulling her nipples as I squeezed them. Linda stopped periodically to get a breath of air and encourage me. She raised her gaze to watch my reaction as she struggled to fit more of me into her mouth.

“That’s it, Honey. I love it when a handsome man fondles my big tits. Are they firm enough for you? In a minute I’ll let you suck on them. I love to have my tits kissed and suckled.”

As she resumed inhaling as much of my cock as she could fit into her mouth, I felt an explosion working its way from my bowels. “Uhh, Linda. I think I’m going to have to cum. I can’t hold it much longer. Maybe you’d better stop so I don’t squirt in your mouth.”

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