You see books and articles about "A life in pictures" or maybe "A life in music." That got me thinking about my own life, and in retrospect, many of the most interesting and enjoyable moments seemed to revolve around sex. What follows is my early high school and college days. It brought me out of boyhood and into manhood. I hope you enjoy it even a fraction as much as I have.
My first time was totally unexpected and played an important role in leading me down the path I followed.
We lived in an average middle class, integrated neighborhood. Both my parents worked. They had decent jobs. We—me and my sister, who is two years older—never really lacked for anything, at least anything important. To supplement my allowance, once I started high school I cut grass to earn money.
The Robinsons were one of my first customers. They lived next door. Mrs. Robinson worked from home. She called it telecommuting. It had something to do with PR. and advertising. Mr. Robinson was in appliance sales; he traveled a lot.
It was by far my favorite yard to take care of. During the grass cutting months, Mrs. Robinson, Jacqui, was almost always in a bikini, sitting in a chair or reclining on a chaise lounge, with her computer, working on something.
She had a dream body. Her well-formed breasts were barely contained by the string and two tiny triangles that made up the top of every bikini she wore. The bottoms were always a small triangle in front, with a larger one covering only part of her perfect butt. Like the top, both pieces were held in place by tiny strings.
The sight of her always gave me a hard-on, which was somewhat visible under the lightweight shorts I always wore when doing yard work. This became embarrassing at times—the times being when she would bring me a glass of cold water or an iced tea, along with one for herself, and stay as we drank, making small talk. She was so easy to talk to, it just tended to make things—and me—harder.
It wasn’t like I didn’t know what I was somewhat showing. When our parents weren’t around my sister called me Mandingo boy and I called her “TT” for tiny tits. It was her nickname for me that confirmed my strong suspicions—I was endowed substantially larger than most other guys.
When she first called me that, I didn’t get it and asked her what she meant. She told me and added, “And I should know.” She was sixteen and having sex, so I figured she really should know.
In the intervening years I went through various mental stages, ranging from frequent embarrassment to taking great pride in myself and my sexual endowment. Still, thus far my only first-hand sexual experience was literally with a hand—my own—but I believed when it did happen with a girl for real it would be wonderful.
So, on a very hot Saturday, during the summer between my sophomore and junior year in high school, I was doing Mrs. Robinson’s yard while, as usual, dreaming of doing Mrs. Robinson. She was out back in her usual skimpy attire and Mr. Robinson was away playing in a golf tournament. Upon finishing, and not having received my usual cold drink, I was dripping in sweat—meaning, among other things, my shorts were clinging to me, amply displaying my growing hard-on as it responded to Mrs. Robinson's generous exhibit of her own remarkable assets.
As I went to gather my equipment and leave, Mrs. Robinson arose and came over to me, saying, “Jack (my name is Jackson Pope), come with me and we’ll get something cold.”
“Sounds great!” I replied and followed her into the house. The following her part was great. She could have just jumped off a page of Playboy. Her rear triangle covered about half of what I thought was the most perfectly shaped ass I had ever seen, especially in real life, and now I got to stare at it wiggling invitingly in front of me.
Not to mention the vision of her long, flowing hair and occasionally a glimpse of the side of a boob when she would turn and smile at me as we approached the house. Now that I really was rock-hard and it really was showing, embarrassment had set in. There was nothing I could do but try to ignore it.
Once in the kitchen she was about to get us drinks when she turned to me, her eyes playing over the display of my manhood, and said, “Jack, you’re totally overheated and sweaty. Go take a quick shower to cool down. You’ll feel much better.”
I was about to protest when I realized it really would give me a chance to cool down, in more ways than one. I followed her to the bedroom, my cock straining at the front of my thin shorts, where she told me to take my time and enjoy myself. Thanking her as she left, I stripped and entered the shower. The large showerhead made the water stream over my naked body; it felt wonderful.
A few seconds later I heard a sound and turned around. Mrs. Robinson had just walked into the shower—naked! I was paralyzed. There I was, facing this beautiful goddess of a woman with my hard cock sticking straight out. A black man-boy in a shower with a gorgeous, horny, married white woman.
“Ohhh... Mrs. Robinson—“ I realized I was speaking to her beautiful breasts, my eyes locked on her large, erect nipples.
“Just call me Jacqui,” she said with a seductive smile.
“Ahhh... Well... Jacqui I, ah, I’m not sure we should be—“
“Don’t worry Jack. I’m totally sure we should be.” Her eyes shifted to my cock. “You’re quite the young man aren’t you. That’s some weapon you’ve got there. Are you licensed to use it?” she said with a devil-may-care laugh.
Just then, she lightly touched my cock; my hands tensed and the bar of soap I was holding squirted away and smacked on the floor. Reflexively, I went to pick it up. “I’ll get it,” she said, quickly kneeling down in front of me and continuing, “I think I’d better get this nice and clean for you.” She covered my cock and balls with soap and began stroking me. Good god, the feeling! I used to think jerking off was fun.
“Oh my god,” I mumbled as she slowly moved both her clasped hands up and down my hard length. Having never experienced a woman’s touch there, let alone her stroking it like it was the most valuable thing on earth at that moment, had every nerve in my body pulsing, pushing the orgasm on me, my cock impossibly hard and eager.
I was so close anyway, and when she began to expertly fondle my aching balls it was just too much. “Jacqui, if you don’t stop I’m gonna… ohhh, oh FUCK!” My legs were trembling as I came, and I struggled to stay standing. I was embarrassed about coming so quickly, but it still felt incredible as jet after jet of my spunk shot out.
She must have realized it was going to happen ‘cuz my dick was immediately in her mouth, her eyes staring up at me as the feelings quickly ran through me. I watched her lips suck at my pulsing, throbbing cock. She blinked once with each spurt, and when I’d finished, she leaned back and swallowed every last drop!
“Jackson, Jackson, Jackson, you pack quite the punch, besides being quite tasty.” She kept stroking it as she stood and continued. “Let’s get you fully cleaned up so we can fuck. I’m just dying to have this huge cock in me. Never been this close to one this big before and I’m sooo looking forward to it stretching me into orgasm heaven.”
I was just beginning to process her “...so we can fuck.” comment.
“Mrs. R—“ She stared hard at me. “Okay, Jacqui... I’m not sure about—“
“I’m sure, and that’s all that counts right now. Don’t tell me you don’t want to fuck me, because your cock says otherwise. You think I’m too old for you. You’ve got some little sixteen-year-old rookie hottie. Is that it?”
“Na... no, Mrs… umm Jacqui. None of that. It’s just that... Well I’m...”
It must have hit her. “You’re a virgin aren’t you? That’s what it is, you’ve never dipped that enormous wick in a girl yet, and I’m turning you into a bundle of nerves. That’s it isn’t it?” She hugged me tight, squeezing her luscious boobs tight against me. “Now tell mommy the truth. Everything’s going to be okay.”
It was a huge relief. All my embarrassment fell away when I simply said, “Yes. You’re right. I’ve never done it. I don’t want to disappoint you.”
Still holding me, my hard dick now being squeezed between her wet, slippery legs, she told me, “Now I’m doubly thrilled! Oh baby, I’m going to take such good care of you. You’ll never disappoint me. Let’s get us dry and in bed. We’ve got some serious reveling to do!”
I was excited beyond my wildest dreams, my cock straining with arousal. Going with the flow was my new watchword for the day. Everything about that afternoon was memorable from just making out—god she could kiss—to playing with her boobs; squeezing, sucking, pulling her swollen tits, hearing her moan when I sucked her hard nipples.
And my god, exploring her beautiful, soaking wet pussy—my first taste of a hard, aroused clit, and what type of response I could wring out of her, and I was hooked. It all culminated with her moaning, “Oh my fucking god” as she first guided me into her, and then I took over, pushing to my full depth, amazed when she took every bit of my big cock inside of her. “Oohh, Jack, my god! It’s unbelievable. I’m so fucking stretched! Fuck me Jack. Pound my pussy with all you got!”
And I did, going so deep that my heavy, aching balls slapped against her perfect ass with each thrust.
What a glorious feeling! I had imagined it so many times. Those thoughts never came close to the reality of being gripped in her hot, slippery tunnel, the feel of her soft, wet pussy touching every bit of my cock, gliding back and forth, each thrust triggering more moans or outbursts from her:
“God, you’re so hard, and sooo fuckin’ huge! - Yes! Yes, yes, yes! - Pound me Jack, pound me! - Damn, you’re ravaging me. I’ll... Oh fuck Jack, I’m gonna cum! Fuck yes, I’m coming”
She began to shake and gripped me with seemingly superhuman strength, her pussy clutching at me almost causing me to lose control again.
“FFUUUCCK!”
I held myself off her as she suddenly collapsed and lay gasping, her body still twitching a bit, my cock still clutched inside her tight heat.
“Come down here Jack. Lay on me, I won’t break.”
I eased my body down ‘til she had my full weight.
“You’re fuckin' amazin' stud! No one has ever come close to what you just did to me.”
We lay like that for a few seconds or minutes. I had no idea. I was in a daze. This was not how I had imagined my first time. Well, maybe in my Playboy Bunny or Penthouse Forum dreams, but not in my reality dreams. I did have a girlfriend, but so far she was maintaining her, “I love you, Jack, but I’m not ready yet. You understand, right?” position.
As I was contemplating how much better I liked Jacqui’s position – on her back, legs up and spread and me between them - she brought me back to reality. “Such stamina you’ve got. You didn’t cum yet. Good! Roll off and do me doggy. I gotta have more!”
Still speechless, slightly in awe of the power of sex, I rolled onto my back as Jacqui grabbed a hair scrunchie from her nightstand and flipped her hair into a long pony tail. She leaned over and began to once again suck my cock. “I don’t think I’m ever going to get enough of this big thing. So what do you think of your first time so far, Jackson?”
Now I had to talk. “It was fucking amazing! You have always been my image of the perfect woman... Now don’t laugh at me—“
“I’m not laughing at you, I’d never do that! I’m sort of laughing at myself, I guess. No one’s ever called me the perfect woman before. Too bad I’m not single and you’re not fifteen - or so - years older. You know, as far as I’m concerned, this is not going to be our first and only time. I hope you make many more visits and they don’t have to be limited to when you are doing yard work. Anytime I’m alone is fine with me. Is that too much for you?”
“Ahh... You kinda surprised me with that... but no, it’s definitely not too much for me. Anytime you say. This is amazing!”
“As long as we’re careful and you know for sure I’m alone for the day, or night; we gotta be smart about this, but then, anytime.”
Now my mind was emboldened and back in the game. “You may get tired of all my visits,” I replied laughingly.
“I highly doubt that! Now get behind me and work that magic again. Put this big boy back in me, hold my hips tight and don’t be shy about slapping my ass and pullin’ my hair. Fuck me hard and deep, and don’t stop until you cum this time.”
She was already on her knees as she said that, her ass in the air, and it only took me seconds to get in position and begin rubbing my rock-hard cock on her dripping slit. A few passes and it was as soaked as she. It slid in easily, all the way to my balls.
“Fuck yes, Jack! This is better than the first time. The stretching feels magnificent! By god, Jackson, you do fill a girl’s pussy to the limit. Now FUCK it!”
Emboldened, I needed no further encouragement. This time I started slow. I wanted to savor the feeling of her pussy enveloping and conforming so perfectly to my cock—it was breathtaking. I relished the new and somewhat indescribable feeling and became mesmerized by the sight of my dark, thick shaft sliding in and out of her wet, pink pussy, and the way she was stretched around me; I thought I’d never seen anything so beautiful!
She once again brought me back to reality. “Faster! Harder! Slap my ass. Grab my hair. Pull me back into you.” I hardly needed to do that, because she was already eagerly thrusting herself backward onto my cock, but she seemed to want it, so I did as told.
Smack, smack went my hand against her ass as the other reached for her long ponytail, pulling her head upright, my full length impaling her and my balls slapping against her pussy with each thrust.
“Fuck yes, Jack! Fucking take me! Make me yours. Beat my ass.”
She moaned and squealed as I pulled her hair tight, her ass beginning to redden as I slapped it. It was not long before she went screaming into her first orgasm. I held on tight and kept hammering her coochie.
She begged for mercy several times as orgasms approached; I never gave any as her orgasms seemed to almost ravage her. Finally, it was my turn. Never speaking, I felt it coming, the rush building, the immense pressure and when it burst I pushed all the way into her and just held her even tighter as my balls pumped my seed deep in her body. She, on the other hand, came one last time as my cock spasmed and flexed inside of her.
“Ohhh shit, Jack, so big! I feel your jizz in me! Fill me, I’m cumming again! Ohhh FUUCCCK!”
Holding her up as long as possible, I finally pulled out in a gush of cum and fell to the bed. She went face down next to me, moaning slightly.
When we both started to move, I noticed my cock was still semi-hard. She glanced at it and smiled, then looked at me, saying, “You’ve beaten me silly for today. Maybe next time.” Then we rolled out of bed.
We had a much more sedate shower than the first one, although she couldn’t seem to keep her hands off my junk, and I discovered that I loved the way her puffy, just-fucked, cum-filled pussy felt. Mostly we had more discussion about her “anytime” offer. I took her up on it many times and many ways before I graduated and went off to college. In quiet times I sometimes wonder how life worked out for Jacqui. We never saw each other again after I left for college, but I’ve never forgotten my first, or subsequent, times with her.
Then there was college.
I had always been interested in how things worked. Through my middle and high school years I think I probably took apart and put back together everything in our house that lent itself to that task. Lamps to lawnmowers, they all eventually found themselves in pieces and then reassembled, always working as good or better than before I got my hands on them. I was born to be an engineer.
School came rather easy for me. I maintained a 3.75 GPA through high school which led to a full scholarship to college. However, being somewhat nerdy and studious didn’t mean that Jack was all work and no play. I was recruited into the fraternity with the reputation as the party frat on campus. I was their only black member, but never felt ostracized or discriminated against, even though suspecting I filled a certain, unspoken, bare minimum quota of some sort.
We all had nicknames. Mine was Griffon. I never knew exactly how that came to be but always suspected it had something to do with my endowment, which was well known among my brothers. Perhaps I filled their “big dick” quota, because more than once I heard “mandingo” in conversation, but it was never spoken to my face.
That knowledge also became fairly common among the girls that came to our almost weekly parties. After the alcohol had set in, I would get all kinds of queries, ranging from “Wanna dance?” - “Is it true?” - “Can I see it?” – “Can I feel it?” to “Let’s fuck!” Once I got used to it, the curious looks on their faces always gave away the question they were going to ask.
I learned quickly that these were not the girls I knew in high school. These girls were seriously horny young women, bordering on Jacqui-esque style sex. When they were down for something they were 100% down—like nail me to the floor hard and long until I’m screaming and my eyes are rolling back in my head down.
One of my more memorable early experiences was with BettyJo, better known by her initials, BJ—an apt moniker. She was one of our so-called fan-girls. These were the regulars that came to most of our parties and invariably ended up having sex with one (or more!) of the brothers before the night was over. This particular night was my turn.
It had only been a few weeks since I had graduated from a pledge to a brother; a frat brother not a black bro; I already was one of those. The fan-girls that had more or less ignored us as pledges now gave us the full we-think-you’re-the-hottest-thing-ever treatment.
So on this particular Saturday night I was moving through the large, crowded common room, beer in hand. The music was playing loud, people were dancing, but the real action had yet to start. It was still early. Most of the girls were in a group talking and sipping their drinks. The guys, including me, were checking out the females, picking the ones they would soon be moving on. It was the unacknowledged preamble to the night’s festivities.
As I was about to approach the girl that had caught my eye, I felt a tap on my shoulder. As I turned, she said, “Hi Jack, I’m BJ. I love to meet the new brothers. You picked a great frat to join.”
Standing before me was one of the most beguiling women I had seen on campus. She was about 5' 5", athletic build, streaked blond-brown hair past her shoulders—pretty much a knockout looks-wise. But it was the rest of her that was breathtaking. She had on tattered, cut-off denim shorts that she’d probably owned since high school. They were so tight they could have almost passed for body paint, and so short there was little left to the imagination. Her top was an equally old denim shirt, unbuttoned halfway down and tied just under her boobs—boobs that had to easily be D cups with outstanding cleavage – and upstanding nipples!
Being with Jacqui so much had liberated me from my shyness around women, especially white women, but I have to admit to momentary speechlessness seeing BJ. Fortunately, I quickly recovered, and forcing my eyes to stay focused on hers, said, “Hey BJ. It’s a pleasure to meet you. You look absolutely dynamite! I see you're drinkless. Let’s go get you fixed up.”
I slid my arm around her waist as she looked me in the eye and replied, “Such a gentleman. I love a man who always looks out for his lady.”
I loved that and wondered, was she my lady? At least for the night, I thought. I promptly retrieved drinks for us and suggested, “The music is quite loud. How ‘bout we go over to one of those couches and get to know each other in a less noisy, crowded spot.”
Snuggling closer to me, she replied, “I’d love that. This feels so good, being close to you. I understand you’re here on scholarship to become an engineer.”
It never really dawned on me to wonder how she knew that or other things about me that came out later in our conversation. I was infatuated.
Guiding her to one of the old, soft leather couches, we sat close, my arm around her shoulders, her left breast pressing into my side. That’s when my erection started, and I had little doubt that she noticed.
We talked about the college, our majors; hers was nursing. Then it turned to personal faves: music, phones, clothes (personal and opposite sex), food. By then I had started to caress her. My hand brushing her neck and shoulder with occasional ventures a bit downwards; I received no blowback. Then there was the first kiss. We both turned at the same time, a soft buss resulted. That was followed by a full-on, tongue twisting, lip pressing kiss. My hand eased down to discover a braless, soft boob and rigid nipple, which I began to squeeze and caress. This brought on moans, our bodies pressing together.
“I’m thinking we should find a very private area where we could continue this in a more intimate way.”
With a big smile she said, “I was having the same thought. You seem to be displaying a rather stiff interest in getting to know me better, and I’m not at all opposed to that. If you think you’re up to it.”
I started laughing. “I’m not at all opposed, and I’m definitely up for it, but I don’t live in the house so...”
“Let’s go down to the basement. I think we might just find something appropriate.”
“Good idea. Let’s bring some beers with us in case we get thirsty while we’re being intimate.” I hastily grabbed some and we headed off.
From that little exchange I found out she was a sophomore, not a freshman like me. She obviously had a much better idea of the house’s layout than me. She’d been down this road—and those basement steps—before, but at this point who was I to care, she was way too much fun.
She showed me a storage room where old furniture and mattresses were stored. Also, the laundry where clean and dirty sheets were kept. We clearly had the same idea. Grabbing some sheets, we went into the storage room, securing the door behind us.
Turning into an embrace, our hands started roaming, clothes started coming off. Soon we were naked, lying on an old mattress with clean sheets.
“Good god, Jack, I’ve never seen a cock like yours! You’re humongous and thicker than my wrist. Your balls are like my biggest ben-wa balls. Fuck, this is going to be amazing, and I’m already so ready for it! Lie back and let me see how much of you I can suck. It looks absolutely delicious.”
She went to town, eventually getting about half of me in her mouth as she rolled my balls in her hand. The girl definitely had skills. Finally, she had to stop, stretching her mouth got to be too much, which gave me a chance to go down on her. She was soaking wet—she hadn’t lied about being ready—and I loved it, another thing I had learned to appreciate from Jacqui.
After kissing and licking around her bare coochie I focused on her erect, aroused clit, sucking it into my mouth and running my tongue around and across it as my hands found her nips. Squeezing, rubbing and pulling them was the cream in the coffee for her. When she pulled my head tight to her, I knew what would soon happen.
“Oh fuck Jack! Fuck, fuck fuck! I’m cumming!”
Her legs squeezed me as they shuddered from her climax, and I kept my tongue busy on her clit as she rode it out. This was going to be a wonderful night.
As she relaxed I climbed up her body until we were face to face, passionately kissing. She reached down and pulled me to her, rubbing the leaking tip of my cock in her slippery juices. When she was ready she guided me to where she wanted me, and a gentle push drove my cock head into her slick opening, which formed around me, tight and perfect.
“Oh my fucking god Jack, that’s so big! You’re going to destroy me and I’m going to love every bit of it. Do it, Baby, do it! Stretch and fill me with that monster. Yes, yes, keep it moving in! Shit, I freakin’ love that big cock!”
“That’s it, Babe. Take it, take it all. Who’s your Daddy?”
“You are! You’re my Daddy. Fuck me Daddy, fuck me deep!”
“Tell Daddy how much you love and want it.”
“You’re the best Daddy, the best fuck I’ve ever had. Fuck me hard and deep. Make me scream! OH FUCK YES! Like that Daddy.”
She needed a bit of teasing so I slowed down and only went about half in, enjoying the way her pussy squeezed me tight, and the way she moved, frustrated and trying to take more of my length inside.
“No Daddy, no! Don’t stop! I’m so close. I need you deep inside me… I… I need to cum Daddy. Pound me Daddy! YES Daddy, YES! I’m gonnaaa... gonnaaa cum. Fuck yes Daddy. Fuck meee. Ahhhhh!”
“That’s it Baby, keep quivering and keep cumming, cuz I’m not stopping. Daddy’s gonna give you more, and then I’m going to fill you up.”
She gasped out, “Oh Daddy you’re driving me crazy. I’ve never... Never felt... Felt like this.” Still gasping she went on, “Please Daddy, please. I... I need... Need you fucking me. I need your big cock. Oh god I’m so... So going to explode.”
That’s when she regressed to just moaning and whimpering. She was riding an orgasmic wave in whatever mental world she was thrashing about in, chain-cumming as I drove my cock deep inside of her.
That was the beginning of a long, fun-filled night. I had learned stamina from Jacqui and used it to my utmost with BJ. I came three times, filling her pussy with my spooge each time, and each time she felt my cock pumping and spasming inside of her she came again; in fact, BJ’s orgasms were countless. Being determined to drain her to the point of complete exhaustion, we stuck to just missionary and doggie positions, both of which provided for deep penetration, which she loved.
She was in no condition for cowgirl or anything that required effort on her part. But, well-lubricated with her own arousal juices and my cum, she just took what I had to dish out and loved every minute of it, even though by early morning she admitted that she had no more left, and that she’d never been so sexually spent in her life.
Exhausted, soaked in sex-sweat and cum, we fell asleep: me on my back, BJ with her head on my shoulder, draped across me as my cum continued to leak out of her. The sun coming through the casement windows finally woke us around noon. I moved first, causing her to move. We looked at each other and broke out in laughter. Neither one of us knew exactly why but chalked it up to the unbelievably monumental fun we had that night, and the totally uninhibited and passionate way we’d connected.
Even though BJ and I never developed a romantic interest, we stayed lovers ‘til she graduated. There were periods where one or both of us were involved with someone. During those times we mostly, I do mean mostly, refrained from our intimate encounters, but neither of us developed a lasting, loving relationship with anyone and the sex between us remained intense and deeply satisfying.
I still believe to this day that there was some karmic sexual synergy between the two of us that kept us connected but also kept us from a permanent bonding.
During my four years of college I had numerous sexual adventures with different women. Many of them were the result of our frat parties. I became a known quantity, and there were always girls (some with steady, but apparently less well-endowed, boyfriends) that were curious, that wanted to have the experience, to try it on for size, so to speak. Usually, I was only too happy to accommodate—merely as a public service, of course!
The local bars and dance clubs also proved fruitful in meeting lovelies of the opposite sex, and that is where I met the three different women I had somewhat long-term relationships with. For one reason or another they all faded. Cheating was never a known reason on either side, things just didn’t work out.
But while it was working the sex was magnificent. In each case I was their first guy of more than average size and they were enthralled. Having matured a bit, I was happy that although my size was a big plus, it was not the glue that held us together for however long it lasted. It was like the ice cream on pie a’ la mode, not necessary on the pie but it made it extra special.
I graduated having been hired by a great company in Washington, D.C. I left my college days behind with fond memories, looking forward to an exciting future in a new city with a new job and new friends.
