I remember the day his family moved in next door very well.
I was gawky fourteen year old, ‘soon to be eighth grader’ when I first met Jack. Jack’s family was moving to Ohio from Providence, Rhode Island. They bought the house next to ours.
Jack was a handsome, athletically built seventeen year old. He was entering the eleventh grade.
I had just completed the seventh grade. I was very much a tomboy who liked sports. I played on the girl’s basketball team. I was a good student, who made good grades. In many ways, I was every parent’s dream.
However, I was not overly feminine, sexy or petite. I had shot up to 5 ft 9 inches in height, and I was rather thin; almost skinny. At age fourteen, I was not the cute little ‘cheerleader type’ that the boys my age sought.
At the time Jack moved next door, I was struggling with the changes occurring in my body, and struggling with the transition from a little girl to a young woman.
To be quite honest, I did not like the feelings I was experiencing as I labored through adolescence. I particularly did not like the expectations that went along with ‘being a lady’. I did not like the fact that boys could still be adolescent creatures who could do and say what they wanted, but I was expected to act ‘lady-like’. The double standard between genders simply made me mad. And in many ways, this anger showed, particularly to boys my own age.
I thought that the boys my age were immature jerks. And far too frequently I let them know how I felt about their antics. Most boys in my social circles were crude and rude. In many cases, they were not even terribly clean! They were unsure of themselves and often acted like jerks to hide their own insecurity.
Their insecurity and bad behavior, coupled with my own gender-based anger at society’s expectations of women, served to convince me that I really did not enjoy or want the company of boys my own age.
I realize now, looking back, that I expected too much from them. After all, they were struggling with the transition to adulthood too, just as I was. But I did not have this level of understanding or tolerance when I was fourteen.
On the other hand, Jack was as close to perfect as any male can be. To me, he was gorgeous. He was 6 ft, 3 inches tall. He had excellent build; short brown hair; and pale blue eyes. But more importantly, he was nice and very smart. He was also mature and worldly.
I would soon learn that Jack earned the role of starting forward on the basketball team and was honored as an all district receiver on the football team at the all-boys Catholic school which he attended. He even garnered some interest from college coaches at some of the smaller, less ‘athletically prestigious’ universities on the east coast.
Every chance I got, I would attend his games to watch him play and cheer him on. I loved watching him play. I will also confess that I felt little pangs of jealousy when the cheerleaders would fawn over him after the games.
I knew that he thought of me like a ‘little sister’ of sorts. To me, he was more than a big brother figure; he was the epitome of what I wanted in a male.
Jack and I both attended parochial (Catholic) schools in northern Ohio, in the suburbs of Cleveland. Unfortunately, we did not attend the same school, and we never would. As I mentioned, Jack attended a large Catholic ‘all-boys’ high school, and I attended the ‘all-girls’ Catholic school six miles away. We would never encounter each other in school.
Okay, I admit I had a huge crush on Jack. I also realized that as a fourteen-year-old junior high school student, he was completely out of reach; he was simply out of my league. I realized that he never even considered me as a potential romantic partner.
Nonetheless, I worshiped him from afar, and cherished the few interactions we had.
Jack would occasionally join me in my driveway as I practiced my basketball shot. He would give me pointers. He taught me to ‘follow my shot’, ‘block out’, how to ‘protect the ball’. If we played a little one-on-one in my driveway, he would admonish me if I played ‘timidly’. I remember him telling me to ‘stop playing like a girl; you are a basketball player, not a girl when you are on the court’.
He treated me like a real person.
Yes, I had to constantly remind myself that he had no physical desires for me. He was mature and worldly, I was an awkward fourteen year old. Nonetheless, I liked the attention. And I adored him.
For the next two years, Jack and I remained ‘friends’ of sorts. He viewed me as a cute little sister; I viewed him as a beautiful and romantic prince who was simply ‘out of my league’.
Jack graduated and was accepted to Cornell University where he would play football and study journalism. At the end of the summer, he left for college. This was the summer between my freshman and sophomore year. I turned sixteen in August, a week before he left for college in Ithaca, NY.
I did not see him again until the following summer, when I was entering my junior year. Much had changed during these nine months. Objectively speaking, I had blossomed nicely. I had transformed from an awkward fourteen-year-old that he first met two years earlier, to a tall, slender, nicely proportioned, attractive young lady who was two months shy of her seventeenth birthday.
I am not bragging when I honestly say, I was more than just attractive, I was pretty. I had long blond hair, large green eyes, firm, perky 36C breasts and long shapely legs that were topped by a firm yet round butt. Yes, I could turn heads.
Despite blossoming nicely, I was still completely inexperienced with boys. I still attended all-girls Catholic high school, which limited my exposure to the opposite sex. The few dates I had been on with various boys, had all been quite unfulfilling. Boys my age still seemed immature and insecure. They wanted one thing and I was not prepared to give it to them. No, the thought of being ‘pawed’ and ‘slobbered over’ by these horny teenagers had virtually no appeal to me.
But I never forgot Jack and I often wondered about his ‘experiences’ at college. I wondered if he had a serious girlfriend. And in the same context, I wondered if he ever even thought about me, even for a second. And recognizing that I had matured nicely since the last time he saw me, I openly wondered if Jack would view me any differently if our paths crossed this summer?
Jack returned home from Cornell in mid-May, 1989.
He had finished his freshman year in journalism. I knew from his parents, as well as from monitoring the sports page in the local news paper that he also had played football for Cornell in the Ivy League (although as a freshman, he did not actually have much playing time). From all appearances, Jack seemed to have survived college intact.
Within a day or two of his return home, I happened to be outside when he drove up. I ran over to greet him.
“Welcome home,” I shouted from across the yard, as I ran up to hug him. I threw my arms around his neck and he picked me up and twirled me around.
The expression on his face indicated that he was genuinely pleased to see me. And I thought his expression also conveyed that he liked what he saw.
“Well, good lord! Look at this! What happened to that scrawny little girl next door? Well, Little Cindy has ‘grown into a woman’ on me,” Jack said obviously pleased with what he saw.
“I can’t believe it, you look great! You really do,” he continued.
“Well thank you, kind sir. I am glad you approve,” I made a joking attempt at a curtsey and flirted back. I was enjoying the attention and flattery. I was definitely pleased that he noticed the changes.
“Oh, I approve. I definitely approve,” he replied.
I could feel myself beaming from the compliments. Could it be that Jack was actually looking at me as a woman?
“How was school? How did you like Cornell?” I asked with enthusiasm.
“It was hard, they make you work, but it was great. Seriously, Cornell is great. Ithaca, NY is absolutely beautiful. Have you ever been up state New York?”
I shook my head, no. I had seldom ventured outside of my home state of Ohio. He seemed so worldly and mature. On the other hand, I felt like I had never done anything, and never experienced anything of consequence in my short 16 1/2 years on this planet.
“So what are your plans for the summer?” I asked, honestly interested in what this gorgeous hunk had planned.
“I have landed a summer job as an intern at the Cleveland Plain Dealer
working on the night news desk. It really is a great job for me. Unfortunately, I have to work from 10 p.m. to 6 a.m. most evenings. You’ll be seeing me drag myself home around 7:30 a.m. most days. I will be going to sleep while most of the world is waking up,” he responded.
“Well that kind of sucks,” I said with as much sympathy as I could muster.
“Aw, it won’t be too bad. This is kind of a dream job for a journalism major. Most of my classmates are working construction, or worse, food service or something similar this summer. Sophomores usually can’t get these kinds of summer jobs.”
Jack was obviously pleased and a little proud to be working for Ohio’s largest newspaper this summer. I really was happy for him.
We chatted for a few minutes before he started to excuse himself and go in his house.
I wanted to continue the encounter, but I knew he had to go. But I did extend an invitation of sorts for later.
“Well, when you’re not sleeping, come on over and hang out. My parents are both working, so I will be here by myself, just lounging around by our pool, most days. I would love some company.”
I tried to make this invitation sound as innocent as possible, but I wanted to make sure Jack knew I was ‘home alone’ most days. I knew it was unlikely he would act on the information, but I wanted him to have it, just in case.
So that started my daily routine of exercising early in the morning, and hanging out in my bikini in my backyard by our pool hoping to encounter him again.
It was not purely coincidence that I started timing my daily run so that I could increase the chances of running into him as he came home from work in the mornings. I would often be stretching before my run on my front lawn when he returned home.
I did not dress too provocatively, however, I wore spandex tops, sans bra, that highlighted my nipples nicely and relatively short gym pants that showed my legs and butt off to their best advantage. I wanted to remind him that I was no longer that gangly 14 year old he used to know.
My running attire was barely modest enough to avoid unwanted comments from my dad, but revealing enough to entice Jack to come over to chat most mornings as I stretched in front of him. It was a delicate balance I had to maintain.
Now I want to be clear here. I did not have any specific thoughts about what I would do, or would not do, given the chance, with Jack.
I had no sexual experience to speak of. I had never even allowed a boy to feel me up. I certainly was not contemplating a sexual rendezvous with Jack. I was attracted to him and would have welcomed the opportunity to explore the edges a bit, if he was so inclined. I was not thinking ‘sex’ in any way, shape or form.
But I also knew instinctively how to flirt. I certainly knew how to catch his eye with my stretches in my spandex top, and how to sit close to him and touch his hand or leg as we talked, just enough to make him aware that I was here, and I was a woman.
During the first week Jack was coming home from work, we would often talk for 15 to 30 minutes before he would announce, “Well, I am keeping you from your run, and I need to get some sleep.” And then he would walk back to his house.
After a few encounters ending this way, I replied, “So how late do you sleep?”
“I don’t know. I usually wake up around 1:30 or 2:00 o’clock.”
“Well, when you wake up, why don’t you come over and join me at the pool. I can fix you some lunch, or if you prefer, breakfast?”
I tried to make the invitation sound innocent so he could easily decline if he wanted.
“That sounds nice. Are you sure you don’t mind if I join you?”
I could see the smile on his face which told me he liked the idea of joining me at my parents’ pool.
“I would love to have you come over. Just come by when you wake up. My parents are never home before 6:30, so I get lonesome there by myself.”
I could feel myself blush as I made the last comment, realizing that I was being a bit brazen emphasizing that we had the house to ourselves until 6 or 6:30.
“OK then, it is a date.”
I spent the next several hours anxiously waiting for time to pass. I worried about what I would fix him for lunch. Should we eat by the pool or in the house?
I fretted about what I should wear? Should I wear my bikini? And if I wore my bikini, should it be with or without a cover up? Should I put on make up? What music should I have playing? I was clearly over thinking our ‘date’.
This was the first ‘date’ I had with someone I cared about. But was it a date? Or was it two friends just hanging out by the pool? Jack had called it a ‘date’, but what did that mean?
I was a nervous wreck for the next few hours.
It was just after noon when he knocked on the back door.
I answered and said, “You are early.”
“I’m sorry. I could not sleep. I kept waking up. I think I was anticipating our lunch,” he replied, “If I am too early, I can come back later.”
He was so cute. He was actually nervous about our lunch date. This was definitely a good sign.
“No, not at all. Come in. I just wasn’t ready yet. Come in and I will fix us something to eat. How does a turkey sandwich sound?”
“It sounds great,” he responded.
“OK then. What will it be? Mayo, mustard, American cheese, Swiss?”
“Mayo, and Swiss.”
I made two sandwiches, got some iced tea and we ate together at the kitchen table. Jack was wearing his swim trunks, a t-shirt and sandals. I had on my red and white striped bikini, covered up with an oversized t-shirt. The bikini had a halter top. The bottoms were essentially two triangles that tied in a knot on each of my hips. I knew this bikini accentuated my ‘assets’ to their best advantage.
We finished eating and went out to the pool area. Jack kicked off his sandals, and pulled his t-shirt over his head. He looked like the statue of Adonis standing there in front of me. The muscles in his chest and arms rippled; his abdomen was tight and firm and his legs were thick and muscular. And yes, he had a very nice butt.
Yes, he looked great.
I took a deep breath and removed the t-shirt. I was now modeling my most flattering bikini. I could feel the blood rush to my face and chest. I knew I was turning a deep crimson at the awkwardness and embarrassment of standing here like this.
But Jack just smiled appreciatively and said, “Cindy, you really are a pretty girl.” Then, before I could respond, he turned and dove into the pool.
I sat on the edge of the pool, my legs in the water. Jack swam the length of the pool a couple of times before popping up from under the water right in front of me. He placed his hands on my knees to hold himself against the side of the pool. This forced my legs apart slightly, allowing Jack to move between my legs.
(I realize that as you read this, you are probably thinking, big deal, right? I mean, I know that there was nothing really overtly sexual about any of this.) But sitting there in my bikini, with this beautiful college student between my knees did seem very intimate and sexy to me at the time. In fact, it still does. And by pushing my knees apart this way, Jack now had a completely unobstructed view of the gusset of my bikini bottom.
I felt myself blush as I realized that the only thing between Jack and my vagina now was a very thin, 2 inch wide strip of red and white striped material. I felt very exposed. And I will confess, I liked this feeling of exposure. It was strangely exciting.
We talked and flirted for several minutes with Jack floating between my knees. I saw him glance several times directly at the gusset of my bottoms before catching himself and returning to look directly in my eyes. And while it embarrassed me a bit, I am forced to admit that I liked the fact that looking at my crotch was such a temptation to him. I liked it a lot.
Finally, Jack pushed away with a huge splash back into the water.
I stood up. I caught my reflection in the large bay window from my living room. Yes, I looked good in my bikini. I noticed my nipples were hard as pebbles, poking through the fabric of the bikini top. My erect nipples were prominently display for Jack to see. I knew he noticed them too.
Jack got out of the pool, dried off and asked, “I hate to be a pest, but do you have any sunscreen?”
“Sure, I will get some.”
I returned a moment later, expecting to hand the bottle to Jack, but as I approached, he turned his back to me and said “Would you put some on my back?”
I know it sounds silly, but honestly, I was nervous rubbing the lotion on his back. This was my first real ‘physical contact’ with him. I poured some lotion in my palm, set the bottle down, and began massaging the slippery cream into his broad shoulders.
“That feels good. You have great hands,” Jack said appreciatively.
With his encouragement, I massaged his muscular shoulders more firmly. I then slid my hands down his back and spread the lotion, covering his entire back. I was not sure where we were headed. So I stopped.
“Can I put some lotion on you? You don’t want to get burned,” Jack offered.
His question surprised me. I had not anticipated this.
“Sure. I’d like that.”
The words escaped my mouth before I had a chance to process the question.
“Here lie down on the chaise long and I will rub the lotion on you,” Jack said it so matter of fact, I simply nodded and did as he instructed.
Jack took a large towel, folded it several times and placed it on the concrete beside my lounge chair. He then knelt on the folded towel next to me.
Jack took my hair and moved it away from my back, placing it over me shoulders. Then he began applying the lotion to my shoulders. His touch felt wonderful as he massaged my upper back. I silently relished the touch of his strong hands.
He then moved to my lower back, rubbing the lotion in a circular motion into my flesh. I expected the massage to stop there, but then Jack got up and knelt next to the chaise lounge and began applying the lotion to the back of my legs.
“Is this OK?” he asked without pausing.
“I guess so. It feels great, but you don’t have to do this,” I replied with a nervous stutter.
Jack laughed and replied, “Cindy, this is not a chore or a punishment. I enjoy doing this.”
I was not entirely sure what ‘this’ was. But I enjoyed the massage. But I was uncomfortable and nervous.
Jack started working his way up my legs towards my buttocks. I suddenly felt my heart pounding in my chest as he took the leg hole from my bikini bottom and moved it higher, exposing the cheeks of my ass slightly more. By adjusting the material of my bikini bottom, he had made it more like a thong without uttering a word.
I could feel me face redden and burn from embarrassment. I did not know what to do or say.
I was not comfortable with this, but lacked the confidence, or the will, to say anything. So I lay there silently, my heart pounding and my ass partially exposed as Jack applied lotion to the sides of my butt cheeks. I must admit, having my butt rubbed this way felt great, but it seemed terribly inappropriate to me at the time. I just knew that I should not be allowing this familiarity.
I was now suddenly aware of my clitoris, which seemed to be awakening.
Finally, after two or three minutes of a very enjoyable ‘butt rub’, I managed to say, “Thank you” and sat up, indicating the massage was over.
I reached down and adjusted the material of my bikini bottoms, returning them to their normal position, covering up my ass just a bit more. I was simply going to ignore the fact that seconds earlier, Jack was feeling my ass!
As I turned over, I was surprised to see the large tent in the front of Jack’s trunks. He had gotten a sizable erection while touching me. I was shocked, flattered and embarrassed by the obvious bulge in the front of Jack’s pants. I tried not to look at it, but my eyes kept straying towards his crotch as I tried to make small talk.
Jack did not try to hide his boner, and did not seem overly embarrassed by it. In fact, he seemed somewhat amused by my discomfort at this large tent pole in front of me.
As I lay on my back, shielding my eyes from the sun with my arm, Jack sat next to me on the chaise lounge. His erection was near eye level to me as he knelt beside the chaise lounge.
Despite trying to simply ignore the boner in his trunks, it proved to be too much of a distraction for me. I could not seem to talk without my eyes returning to the huge bulge Jack was sporting in front of him. Finally, I felt I needed to say something, anything to address the obvious, and relieve my discomfort.
“You seem to have a bit of an issue there,” I said, smiling and nodding towards his erection.
Jack nodded back and agreed, “Yeah, you have created a bit of an issue for me.”
“Me? What did I do?”
“You went and grew up and you became the most gorgeous girl I have ever seen. I just can’t help myself. ‘Little Jack’ is simply paying a tribute to your beauty.”
“Yep, that’s his name.”
“You named your penis?”
“It only seemed right. It seemed so impersonal to keep calling him ‘dick’. Don’t you have a pet name for your…you know…”
He glanced briefly at my crotch to let me know for certain what he was referring to.
“But ‘Little Jack’? He does not look ‘Little’ to me,” I quipped before realizing how inappropriate my comment was. But on the other hand, this entire conversation was inappropriate.
I could not contain my laugh. I continued with a nervous excitement in my voice, “This is so weird. But since you asked, no, I have not ‘named’ my ‘parts’.”
I looked at the throbbing pole desperately pressing at the material in front of Jack’s trunks and asked, “So how long does this last? Will it just go away?”
“Probably not, at least not without your help,” Jack replied.
Again, I could only laugh nervously, unable to think of what to say. I know I was a bright shade of crimson.
Then as if he suddenly realized how uncomfortable I was, his expression changed.
Jack’s voice also changed from joking and flirtatious to serious, “Cindy, I am very attracted to you. And more than that, I really like you. I like who you are. But I also do not want to screw up our friendship. I don’t want to push you into something you do not want, or that you are not ready for. Can you understand what I am saying?”
I nodded but did not speak. I really did not know what I could say at that moment.
I was not sure where this was going, but I was scared. I was scared that Jack was going to tell me he had to leave before something happened. And I was also scared of what might happen if he stayed. In fact, my mind was swirling. I could not identify a scenario that did not scare me at that moment.
Jack reached up and placed his hand on my cheek and simply asked, “May I kiss you?”
I nodded silently. I did not know what I wanted to happen next, but at this moment, I knew I wanted him to kiss me. I wanted that more than anything I have ever wanted in my life.
Jack leaned forward and our lips touched, gently at first and then more passionately. I opened my mouth to accept his tongue. My head was spinning and my pulse was racing.
I wrapped my arms around his neck and he lay down next to me on the chaise lounge.
We kissed passionately for several minutes, our breathing grew faster. I felt his large erection pressing into my legs and groin as he humped his hips from excitement.
With my arms around his neck, I could not interfere when Jack reached up and ‘cupped’ my breast in his hand. Momentarily, I contemplated whether I should try to stop him from ‘feeling me up’. This was new territory for me. No one had ever done that before.
Quickly, I concluded that I did not want to stop him; I knew that I wanted Jack to be the first one to touch my breasts.
I moaned as I sucked his tongue into my mouth as he teased my erect nipple. After feeling my breast through my bikini top for a couple of minutes, Jack slipped the bra up, over my breast, exposing my bright pink nipples to sunlight for the first time in my life.
I felt so wickedly sexy with the warmth of the sun shining brightly on my exposed tits.
I could feel the wetness in my vagina forming and beginning to leak out into the gusset of my bikini bottom.
Jack broke our kiss and began kissing my neck and shoulders, heading down to my exposed breasts. He took my right nipple into his mouth and sucked it, teasing it with his tongue. I held his head against my breast as he suckled at my nipples, moving from one to the other, teasing both them into attention.
My nipples were so hard and so erect. And my vagina was really lubricating now. My wetness was leaking noticeably into my bikini bottoms now.
I could not help rocking my hips slightly, humping my bottom up into the air, demonstrating to both Jack and myself how aroused I had become.
After several minutes, I realized that necking and petting like this, with my breasts exposed in the backyard in broad daylight, was far too dangerous. We could get caught far too easily. Anyone could walk around back and stumble upon us.
“Jack, maybe we should go in the house?” I suggested.
He nodded and stood up, pulling me into a standing position with him. My bikini bra hung loosely around my neck, my tits still exposed. Jack leaned over kissed me again, and teased my saliva coated nipple with his fingers as we stood there.
“Cindy, you are a very pretty girl... very pretty.”
He then took my left hand and placed it on top of the pulsing material in the front of his trunks which was covering his erection. I was shocked, and did not know quite what to do. I did not close my fingers on the penis, but simply allowed my hand to rest there gauging its size. His penis felt larger and thicker than I was expecting. It pulsed under my touch.
Touching his penis excited me, but honestly, its size, its pulsing and the significance of touching Jack’ penis frightened me a bit. I did not know if I was ready for all this.
As my hand rested on Jack’s cock, he said, “That is yours. Only yours.”
I did not know what he meant, but his words scared me. This was going too fast. In the last 30 minutes we had our first kiss. I was felt up, my breasts had been sucked and now I had a boy’s penis in my hand.
Jack then led me by the hand into the house as I tried to pull my bikini bra back down to cover my breasts. I did not know what was in store for me, so I just followed Jack’s lead. As we walked, I tried hard to process these events and determine what limits I wanted, or needed, to enforce. I was not sure how far I wanted to go in this journey of discovery today.
I thought we would resume our necking and light petting on the living room couch, but Jack led me straight upstairs into my bedroom. I wanted to say something, to protest and suggest we stay in the living room, but I didn’t. Something stopped me from expressing my concern about immediately going to my bedroom. I seemed to simply be willing to allow Jack to assume control.
My bed was covered with a bright pink comforter as well as with several stuffed animals from my childhood. I immediately realized that my room looked like it belonged to a little girl, not a woman who was discovering her sexuality. I knocked the stuffed animals from the bed to the floor.
Jack turned me to face him and kissed me again. As we stood, our bodies pressed together, kissing deeply, he unhooked the clasp on my bikini bra and then untied the halter around my neck. Without breaking our kiss, Jack removed my top, leaving my breasts exposed once more. He took my bikini top and tossed it my dresser. My bare nipples were now pressing against his muscular abdomen and chest.
This was an incredibly sexy, erotic and romantic situation.
Jack then broke our kiss, and slowly, while kissing my neck, started to move around behind me. I was not sure what he was doing, but his hands held my shoulders indicting he wanted me to remain standing as I was. So I complied. I stood and allowed him to move behind me. As he pressed against me, I could feel his erection grinding against my lower back.
I opened my eyes to see our image reflected in the mirror over my dresser. I could see Jack standing behind me, kissing my neck and ear from behind while feeling my right breast with his free hand. My left nipple was fully exposed and stood at attention, fully erect, hard as a pebble.
It was a very erotic image in the mirror. I will never forget it.
He then started to slowly move his hand down my abdomen, stopping at the waistband of my bikini bottoms as he prepared to slide his fingers inside.
I reached up, grabbed his hand as just the tips of his fingers got past my waist band. I held his hand firmly.
“Jack, we are moving too fast,” I cautioned. “I am not sure about this. We need to slow down.”
“I don’t want you to do anything you don’t want to do. I don’t want to push you into anything before your ready,” Jack said.
I listened silently as I squeezed his fingers in my hand, preventing Jack from venturing further into my bikini bottom. I was unsure of what I wanted. I knew I longed for his touch down there, but I also knew I was losing control of the situation. I had not planned on any of this happening; therefore I was unprepared for it mentally or emotionally.
I stood motionless for about a minute continuing to grasp his right hand, his finger tips just inside the waist band of my bottoms. He continued to kiss my neck and tease my nipple with his free hand, teasing me, eroding my resolve.
Finally, after a minute or so, my willpower broke. I could not resist any longer. The temptation to be touched ‘down there’ and intimately by Jack was simply too great.
I released his hand and said simply, “I think I want you to touch me.”
When I released his hand, he hesitated for a moment before saying, “Are you sure about this? You don’t have to do this if you don’t want to.”
I nodded, and simply said, “I want you to touch me. I want you to be the first to ever touch me there. Please?”
I wanted him to know that I had never done anything like this before. I wanted him to know how special this was to me. And although he sensed that this was a special moment, I knew he could never comprehend how very precious this moment was, and still is, to me.
With my permission, his fingers slowly moved further inside my bikini bottoms, down past my thin, wisps of blonde pubic hair. I opened my legs slightly. I wanted him to touch me, and more.
When his fingers found my clitoris they sent a shudder through my body and a quiet moan escaped me.
I pushed my ass back against his erection as he stimulated my erect clit. He was getting me so very, very hot. He humped his boner against my ass as he teased my clitoris, making me shutter and moan repeatedly.
I could feel my vagina leaking. I could feel my vulva opening up in small little pleasurable spasms. My physical response to this stimulation was much more pronounced than anything I had experienced before.
I thought about how my vagina responded to my own touching myself while masturbating. This was very different. I was leaking much more profusely into my bikini bottoms now and I could feel my vagina dilating with each glorious spasm.
Jack reached down further between my legs to find the opening of my vagina, inserting the tip of his finger and massaging the very opening, and then returning to my erect clitoris.
“Oh Jack, you are getting me so hot. Damn it, I can’t stand this,” I panted.
I arched my hips back and forth, humping my ass against his cock and pressing my pussy against his exploring fingers. I could feel the lubrication just running out of me. I was having difficulty standing as I quivered with my knees bowed slightly. I was squatting slightly to allow Jack to access my vagina better.
Fearing that I would lose my balance and topple over, I took two steps forward towards my dresser. I placed both my hands on the top of the dresser, and leaned forward. Jack moved forward with me, never losing contact with the opening to my vagina.
Jack continued to kiss my neck and ear as he continued to stimulate me, teasing my erect clitoris as he humped on my ass. After teasing my clit, he would return his fingers to my vaginal opening, causing me to quiver. Then he would return to my clit, before repeating the process.
I still cannot believe how I responded to his touch.
Jack untied the one of the knots on my bikini bottoms that held it together at my hip. The front and back fell apart. I opened my legs a bit and I allowed my bottoms to fall to the floor.
The only remaining barrier to his full access to my gushing pussy had been removed, and my bikini bottoms were now lying at my feet. I was now totally exposed; I was naked and vulnerable.
I looked at my naked form in the mirror. I almost could not recognize the beautiful, sexy woman looking back at me.
Jack guided me to lie on the bed on my back. He kissed me deeply as he continued to explore and stimulate my wet vagina. I could feel myself opening up to accept his probing fingers. He inserted one, and then two fingers inside of me.
I could even sense the faint aroma of my arousal. I had not smelled myself give off this scent before. But now, the scent of my sexual response was clearly present in my bedroom, informing Jack in yet another way how aroused I was. I simply could not believe how I was responding to his stimulation.
I wrapped my arms around his neck and our tongues continued to tease and explore each others’ mouth with a passion that only teenagers can fully experience. I moaned in to his open mouth as his tongue penetrated my lips. I arched my hips up tin time to the probing fingers that were penetrating my vulva. I was beyond reason, beyond thought. I was consumed by lust.
Jack kissed his way down my neck towards my breasts and began to suck on my erect nipples. I caressed his head as he suckled on my breasts while he continued to finger me.
He started kissing down my exposed belly, stopping to kiss my naval. Jack climbed between my legs and began kissing lower and lower. Instantly I realized what he was preparing to do. I was unsure I wanted to allow this. I held his head, preventing him from going lower.
“Jack, you don’t have to do that,” I said with a slight panic in my voice.
“Cindy, you are so sexy, so beautiful. May I please ‘taste’ you?” he asked as his fingers continued to stimulate my vulva and clitoris.
I remember feeling absolutely powerless to resist this incredibly sexy man. However, because of my inexperience, I was not ready to jump into this level of intimacy. But I was so fucking turned on, so aroused; I did not have the strength to resist. After a pause, I released my grip on his head and allowed him to continue kissing his way down my belly towards my wet and open vagina.
I remember biting my lower lip in fear and anticipation as I prepared for another very new experience. I really did not know what to expect.
He kissed my vulva gently for several seconds, stopping to look at me ‘down there’. He was studying my most private parts. I wondered if he was deciding whether to continue?
I blushed deeply. I felt my neck and chest flush with embarrassment as Jack examined my pussy while continuing to finger me. But despite my embarrassment, I did not want him to stop. In fact, I spread my legs open to allow him to penetrate me deeper with his fingers.
I cannot explain it, but despite the embarrassment, I enjoyed exposing myself like this. I liked Jack examining my most intimate parts. He gently kissed my vulva as he studied it.
I did not know how to guide him, this was all new to me. I reached down and shamelessly held my vagina open, exposing my clitoris for his inspection. Jack kissed me right on my little nubbins, my erect clitoris, and I moaned approval.
He took my moans as approval to proceed, and tested my clitoris with the tip of his tongue. The contact of his tongue on my erect clit sent a shot of pleasure through me, “Oh God, Jack… do that again…”
I lifted my ass off the bed to give him better access.
Jack repeated touching my clit with his tongue, only this time, he licked and stimulated me for several seconds before stopping.
“Oh Jack, that’s the spot… God that feels good,” I panted with excitement that encouraged him.
Jack began stimulating me with more enthusiasm, encouraged by my reaction. He flicked his tongue over my erect clit repeatedly, causing me to moan each time.
Then, without warning, he experimented taking my clit into his mouth and sucked on it
“Oh shit, that is too intense!” I shuddered as he took me between his teeth.
I grabbed his head and tried to push him away because of the intensity of him sucking on my clit. But he was too strong, I could not break his suction on my vulva.
“Oh Jack, …. oh god… damn… too intense,” I hissed.
Despite my incoherent protests, he did not release my swollen clit from his lips. He sucked slightly harder as I shook and quaked under his stimulation. I could feel my orgasm starting to build.
Suddenly, as my orgasm neared, I stopped trying to push him away and caressed his head as he sucked my clit.
I was spreading my legs as wide as I could to open myself up for him. I was shameless. I knew I was going to cum if he continued stimulating me this way.
I was arching my hips up and grinding my pussy into his mouth and jaw.
I felt like a puppet and he was pulling all my strings. He was getting me to react in ways I did not know were possible. And he enjoyed having this control over me; making me quiver and react in this way. And truthfully, I loved it too.
Jack continued to suck and tease my clitoris as he reached under me with his hand and began penetrating my vagina with his fingers, first one then two. I was so wet, and so open that, after a little work, he was able to squeeze two fingers deep inside me as he stretched my virgin pussy open.
Once fully inside me, Jack’s fingers found a spot on the front wall of my vagina, up in my uterus, that caused a reaction, a response that shocked both of us. It was a place I did not know existed. Later in life, I learned it was an area that some women refer to as their ‘g-spot’.
I almost screamed as he began massaging the front of my womb. “Oh my god, oh.” I said between incoherent moans and other sounds of pleasure.
Up till now, Jack’s touch and kisses had me aroused and moaning, but the massaging of my uterus at this spot caused me to buck and shake uncontrollably. I was reacting in a way I did not know was possible.
I was impatiently lifting my ass off the bed as I bucked my hips wildly.
While keeping his lips locked tightly on my clitoris and sucking my clit firmly, Jack was massaging my inner walls and driving me to an earth shattering climax. My orgasm came upon me suddenly and violently and I responded to it more vocally (louder) than I ever intended. I grasped a pillow and held it to my face to muffle my own screams of pleasure.
Holding Jack’s head in place with one hand, while clutching the pillow with my other hand, I continued to cum and grind my pussy into Jack’ mouth. I bucked my hips as I humped against his invading fingers. I lifted my ass off the bed to push his fingers deeper into me as wave upon wave of pleasure rocked across my frame.
“Oh God… damn, Jack… don’t stop…” I moaned and panted.
Fortunately for both Jack and me, we had the house to ourselves. I hoped his mother was not outside next door for fear that she would hear my abandoned screams and moans.
After several waves of my climax rocked me, my clitoris began to be far too sensitive and I violently and forcefully pushed Jack’s head away from my crotch, breaking his suction hold on my clitoris. But he continued to move his fingers inside me, stimulating my uterine wall as I tried to come down from the orgasmic high.
“Oh Jack, you need to stop. You need to let me come down.”
Jack smiled broadly with a pride I had not seen previously and slowly withdrew his fingers from inside me.
I lay there panting, my legs still splayed apart, my vagina still experiencing minor spasms in the post-orgasmic moments. I could feel a combination of Jack’s saliva and my internal lubrication dripping down my vagina and onto the bed.
As I tried to recover my senses, I watched as Jack stood and removed his swim trunks. His huge hard cock seemed to spring forth from his trunks as he lowered them.
As Jack started to climb between my legs, I suddenly realized that he wanted to enter me with his penis; he wanted to fuck me! This I could not allow to happen… I was not protected, I could not risk getting pregnant.
“Jack, we can’t. I can’t get pregnant,” I stated with an authoritative tone I did not know I had. "Let me ‘thank you’, another way,” I said almost pleading.
I knew he needed a release, but how? Coming soon: Chapter 2: My first love - I learn about the male anatomy
(This story is dedicated to Jack, the first love of my life. If through some freak of chance, Jack stumbles upon this story published in Lush, I hope he recognizes himself and me and, as he reads it, I hope that he understands how much I cherish these memories, and how grateful I am for the wonderful journey he took me upon 25 years ago this summer.)
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="http://www.lushstories.com/stories/first-time/cindys-first-time-a-journey-of-1.aspx">Cindy’s First Time – A Journey of Discovery</a>