Ladyboys Moving to Thailand and my first Ladyboy
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Syl's First Boy Love free porn video
Hi, I'm Sylvia, but my friends call me Syl.
The summer before my senior year in high school, I was seventeen and already had my driver's license, but no car of my own. I had just gotten my first real job, working part-time in the snack shop of the summer swim club where my family belonged. The swim club was at the edge of the sub-division where we lived. I usually walked there and back, about fifteen minutes each way.
There was a guy named Rick who worked there, as a lifeguard and swimming instructor, who I crushed on. He was two years older than me, and had completed one year of college. He had previously gone to my high-school and I remembered noticing him back when I was a sophomore and he was a senior. Because he sometimes came up to the snack shop and talked to me, with a hint of affectionate innuendo, I had hoped he might like me too. He seemed like a nice guy. My parents knew his parents. They had all gone to high-school together. So, I knew he, like me, came from a conservative traditional Christian family.
Yes, I came from a conservative family. I was a good girl, mostly. And, I was trying to keep that reputation. I fully intended to preserve my hymen as a gift to give my husband on our wedding night, remaining a virgin for him, at least technically. But, although still kind of naïve, I wasn’t as innocent as everybody thought. I looked at some ‘porny’ pictures on the computer from time to time. I ‘jilled’ myself to an orgasm many nights. And the previous summer, when I was sixteen, while away on a mid-August family camping vacation, travelling where no one knew me, I had explored some curiosities.
That previous summer, I had impulsively joined other teens my age in an I‘ll-Show-You-If-You’ll-Show-Me gambling game. So, I had already seen three guy's unzipped cocks. I had also seen one of those guys rather proudly 'jack' himself, and had been amazed to watch him spurt his cum. I had shown my breasts and even let myself be seen playing my nipples with my fingertips, pinching and twisting and tugging them. The other girl had let each of the guys kiss her bare nipples, which she seemed to like although she blushed a lot. But no one had yet seen, or touched, my pussy. I had quit the game before that happened. Scared, the other girl and I had fled the game when the cards required us to bare and touch each other’s pussy.
Later, as I fell asleep for the night, I was already regretting having abandoned the game. I had forfeited my first opportunity to touch a guy's cock. I 'jilled' myself to sleep and dreamt of holding one of those guy's cock in each of my hands as I kissed the tip of the third guy’s cock.
The next morning I considered if I might seek out one of those guys and offer to show my pussy in exchange for touching his cock. But I didn’t. My timidity exceeded my eagerness. My good girl self just couldn’t bring myself to actually proposition a guy like that. Then soon the vacation was over and it was time to go back home. The opportunity had passed.
But now, an early June day of the following year, back at the swim club, a children's swimming lesson had just finished. I was walking on my way to the snack shop past the area where parents observed the lessons. Rick had just started talking there to a pretty girl a little older than me, who I never remembered seeing before. And his swim suit was starting to swell. I was instantly jealous. Quickly I turned my eyes from Rick, who smiled as I passed by, and I looked at that girl and gave her a nasty frown. "Why," I thought, "had she intruded?" At once I realized I really wanted Rick. This desire of mine wasn't just a mere a fantasy crush anymore. I really wanted to be his. I was so mad.
A half hour later, that girl came up to the snack shop window and said she wanted to talk to me. I was still mad and didn’t really want to talk but, trying to be nice, did so anyway. Soon I was glad I had. She introduced herself as Kathy. She was the older sister of one of the girls in the swimming lesson and had just happened that day, instead of their mom, to drive her sister there. I was feeling a little less mad.
Kathy said, "You really like Rick, don't you? I could see your envy of me in your eyes. Please don't be jealous. He and I were in the same circle of friends when in high-school and we were just catching up, because we go to different schools now. He goes to the local college, but I go to the university across the state. I have my own steady boyfriend from there."
"Syl," Kathy confided softly, "Rick said his college girlfriend is away for the summer. So, I think he is available; at least for the summer, and maybe beyond. But, he will have a new summer girlfriend soon. And, unless you do something about it, she won't be you."
Kathy continued, "I think he likes you, Syl. I saw how he looked at you. It was the look of affection, tinged with desire. But maybe he is reluctant to approach you. He probably thinks that you think that he is too old for you; after all, he is in college but you are still in high-school. But, he is worth catching, and if you wish to pursue him, I will gladly help you."
I was stunned into silence, but gave her a huge smile, then started to giggle. Then, she did too. I was feeling better. "Um, yes Kathy. That would be great. Do you really think I have a chance with him?" I was feeling hopeful.
"Seeing how he looks at you, definitely; but you got to beat the competition. Find ways to be alone with him which aren't formal dates. He will be more comfortable that way."
"How do I do that?"
"Well, maybe ask him for a ride home, like if it's dark or rainy, or even if it isn't. He will. And you will be together and away from others. It will get him more comfortable being alone with you. Plus, he won’t be with somebody else." As we finished talking, she said, “I’ll be bringing my little sister again tomorrow and we can talk more then.”
Well, I did it. I asked him for a ride home that very evening. And even though I had to wait until his shift was finished, Rick gladly brought me home.
On the way to my house, Rick said he had seen me talking to Kathy. He explained she was just a very good friend from high-school and although they both liked each other a lot they had never dated, because they were never both unattached at the same time. We got to my house quickly, but then we sat and talked in his car for several more minutes. When I went into the house, my mom asked, "Whose car was that you got out of?" When I told her it was Rick who had brought me home from work she said, "Oh, he comes from a nice family. Just tell him I want him to drive extra carefully when you are with him."
The next day I saw Kathy again. She was happy I had taken her suggestion. She then recommended, "Tonight, tell him you haven't eaten a good meal all day, and ask him to stop somewhere on the way home so you can get something. If he offers to buy, it’s almost like a date; and he is really liking being with you."
Well, I did, and he bought us both hamburgers. We sat across from each other in the booth, talking easily and smiling a lot. Soon that became our daily after-work routine, even on weekend evenings. Well, if his college girlfriend was gone for the summer; I was starting to take her place.
Then one evening going to the restaurant after work, it started to rain. Rushing across the parking lot from his car, he slowed to reach back and encourage me along. I reached forward and took his hand. He gave me a surprised smile and then squeezed my hand. We ran through the rain hand-in-hand. That night he sat beside me, rather than across from me, in the booth. And he asked me out on a real date to a movie. I accepted immediately, eagerly. That night when he dropped me off at home we hugged and kissed deeply. As his tongue danced with mine, his palm cupped my breast through my tee-shirt. It was the first time a guy had done that for me. I was so happy.
A few days later in the darkness of the movie theatre, we sat close together, held hands, and kissed occasionally. After a while, he put his right arm around my neck and shoulder and draped his hand onto my Henley shirt and right breast. I crossed my left hand up to briefly pat his, gently acknowledging his touch but not pushing his hand away from my breast. Then, I twisted slightly towards him, leaned my head against his shoulder, and moved my other hand onto the top of his thigh. His free hand then guided my hand to the crotch of his pants. Nervously, I let it lie there mostly still on his bulge, but my curious thumb softly stroked along the ridge. I was anxiously excited. I kissed his neck; with his left hand he then reached across and opened the two remaining buttons of my Henley. When I didn't object, the fingertips of his right hand slipped inside my loosened Henley and caressed my breast and nipple through my thin sheer bra. My nipple swelled as I enjoyed his light touch. I don't remember the movie.
Afterwards, we went to a nicer restaurant for dessert where another of his classmates was waitressing. He actually introduced me to her as his girlfriend. She smiled to me and said, "You're a lucky girl!" I was so thrilled.
A few days later we both had the day off work and so we went to an early matinee movie. I had planned my wardrobe better. I wore a fully front-buttoned blouse, and a bra with a front clasp which I had purposely bought for him. Again sitting beside me, he put his arm around my shoulder and draped his hand onto my blouse and breast. Again, I gently patted my approval. Then, I turned towards him, rested my head on his shoulder, moved my hand onto his thigh and, as I hoped, he again guided it to his cock. Tentatively, I caressed him, softly rubbing my whole palm along his bulge in his pants. I kissed his neck; he unbuttoned three more buttons of my blouse. I softly moaned my approval as he slipped his fingers inside my loosened blouse and under my bra, and caressed my breast. He gently scissored my nipple between two of his fingers.
Following the movie we went for a nice dinner. As we had our dessert, the sun set. Leaving the restaurant, he drove us to an obscure little park overlooking a small river. Our car was the only one in the small parking lot. As we sat and talked together in the front seat, we began cuddling each other. Still acting the timid good girl, I nonetheless acquiesced to letting him unbutton most of the buttons of my blouse, and let him caress my breasts and nipples through my bra. He again guided my hand to the crotch of his pants, and I discovered he had surreptitiously unzipped and his cock was standing tall and free. My hand gently explored it. In turn, my other hand unclasped my bra, letting it fall open. He cupped my bared breast in his palm and thumbed my nipple. We kissed deeply as we fondled one another. I was so happy.
On the Fourth of July holiday, Rick asked me to go steady with him. Hesitating for just a moment, I quickly debated with myself in my head. I fully realized going steady meant others would presume we were petting each other on our dates. “How would that effect my reputation?” I wondered. Yet some girls who went steady were still perceived to be nice girls in nice relationships with nice guys. “Maybe, I could be too and all would be okay,” I thought. “After all, he was one of those nice guys. He always treated me well, both publicly and privately; and I was falling in love with him.” I didn't want to risk losing him by declining. And, because he was willing to commit to being exclusively mine, I happily accepted.
So we exchanged class rings. As fashion required, I wore Rick's ring on a gold chain hanging from my neck into my cleavage, near my heart. My dad was not pleased I had chosen to go steady, but he didn't object either. I don't think he actually disliked Rick but was probably just afraid his only daughter was growing up too soon, and too fast. My Mom however was pleased I had found a nice guy from a nice family. I think she secretly liked Rick, who may have reminded her of a younger version of my Dad. Years later I learned my Mom had persuaded my Dad it was okay I was going steady with Rick, and if he objected he risked harming his relationship with me.
Since we were going steady now, we began to pet more intimately on our dates. He suckled my bared breasts and reached up my skirt and caressed me through my panty. I stroked his unzipped cock. Sometimes I took just the very tip of him to my closed but pursed lips, smearing his precum onto my lips to then lick and taste with my tongue. But, still trying to be the good girl, I didn’t let him enter my mouth and I didn’t directly touch his cock with my tongue either. But I loved seeing him erupt for me as I stroked and twisted him. I was so happy.
Although, I let him reach up my skirt and caress me through my thin panty, I hadn't yet let him take it off. One time he pushed my panty's crotch fabric aside and directly touched my lips. I gasped in surprise and pleasure. He seemed frightened and pulled back. But smiling, I soothingly said, "It’s okay. I was just surprised. I liked it. But please don’t ever go inside my ‘gina. I am preserving my hymen for our wedding night." He respected that, and just caressed my lips and rubbed my hooded clitty. It was new and arousing. I was so happy.
The next time he fingered me, as he parted my lips slightly but hadn’t quite yet entered my 'gina, I cautioned him not to go deeper. He replied, "Syl sweety, I'm not going to tear your hymen. I just wanted to get some of your joy juice from between your lips onto my finger to taste. You smell so good that I want to taste you too." Then he smiled, and lifted his finger to his lips and licked it, saying, "Mmmm, you taste delicious!"
He was a patient man of his word. Subsequent dates his fingers rubbed me along my mound and pussy, parting my outer lips and circling between my inner and outer lips, sometimes hooking under my hood to touch my clitty, and continued to finger up my wetness between my inner lips from the entry to my 'gina; but he did not try to penetrate me any deeper. And it seemed, he always wanted to taste my joy juice.
One time, after I had stroked him to eruption, he wiped up some of his cum on his finger and offered it to my lips. I sniffed its aroma up close and was intrigued. Tentatively, the tip of my tongue, having a mind of its own, reached out and touched his cum covered finger. He tasted good. My tongue then licked his cum from his finger. We smiled at each other.
When he next offered me his cum wet finger; I again sniffed it, and then touched it with the tip of my tongue. But then, my mouth and tongue went on to fully suckle his finger. I was hooked by the taste of him. Although I was too timid to suck his cock, I was at least going to 'BJ' his cum covered finger and enjoy the taste of him.
Then came late July, and Kathy invited me and Rick to double-date with her and her steady boyfriend, Doug. One Saturday, we travelled across the state to the university, which they both attended, to go to a concert at an auditorium there. Doug borrowed his Dad's full-size car for the road trip, with Doug and Rick sharing the driving. Because he knew where we were going, Doug drove going there but Rick drove coming back. It was very long day, evening, and night. The concert was nice, but what I remember mostly was the ride home.
Traveling back home in the early morning, I listened to Kathy and Doug making out in the darkness of the back seat of the car. I was too embarrassed to turn around and look, it was too dark anyway; but listened intently. At times, I heard each of them moaning softly. I thought they had each, in turn, cum.
Kathy told me privately later, yes indeed, Doug had suckled her breast and finger fucked her pussy, bringing her to an orgasm. And, she had sucked Doug's cock, bringing him to a climax in her mouth. She said, "I love the taste of Doug's cum. I imagine Rick's tastes good too, doesn't it?"
Smilingly, I replied, "Yes he does taste good, very good!" Yet somewhat ashamed, I did not acknowledge I hadn't yet tasted his cum directly from his cock. And although I really wanted to know, I did not dare ask her if her hymen was still intact, afraid to maybe learn it wasn't anymore.
Kathy's comment confused and challenged my morality. Kathy was a nice girl, yet she had openly acknowledged she enjoyed sucking Doug’s cock and being finger fucked by him. But I had always thought good girls weren't supposed to do that, at least not until they were engaged. I was envious of her bold confidence to do as she wished. I wondered to myself, “Could I be that bold too and still be a good girl?”
"After all," I rationalized to myself, "I had fallen in love with Rick. He was so special to me. And, we would probably get engaged eventually anyway." I resolved to dare to be bolder with Rick.
The next time we went parking, when Rick again reached up my skirt, I took a deep breath, asked myself whether I was really sure if I wanted to be bolder with him. Then deciding I did, I invitingly whispered, "You may pull my panty down, but please don't harm my hymen." He then reached up with both hands and pulled it down, past the hem of my skirt to my knees. But wanting to open my knees for him, I pushed it down further to my ankles.
With a big smile, he just starred at my pussy. He said softly, “Syl, your pussy looks amazingly beautiful.” Then he slowly reached out and touched me there, watching himself as he did. Very quickly, I was very wet. Soon he was again tasting me upon his fingers. I was so aroused and felt compelled to let myself orgasm.
So, I spread my knees wider. I parted my lips, rubbed some of my wetness up to moisten my clitty, and circled the pad of my fingertip on my clitty. As he watched me, I 'jilled' myself. He was amazed to see my legs thrash and my back arch as I moaned with pleasure. It was the first time I wasn't alone when I orgasmed, and I was so pleased he was the first one to witness me.
After I calmed, I turned and licked all around the tip of his cock, and for the first time tasted his precum directly from his cock. I kissed the so soft skin of the head of it. But, I still didn’t take him into my mouth. He showed me the wrinkled spot on the underside of the head of it where I could make him cum just by patiently circling my moistened fingertip on it. I did so, until he spurted all over his stomach and chest. Before he offered it to me, I quickly wiped up some of his cum with my fingertip and tasted it. I loved his taste. “Why was I so timid to take him directly into my mouth?” I wondered.
When it was time to go, rather than pulling my panty up, I slipped it off over my shoes. I gave it to Rick as a memento. So that night I returned home pantyless under my skirt. It was the first time I went like that. It felt so naughty, but exciting.
A few days later, when we were again parking in his car, he once again reached up my skirt and removed my panty. I unbuttoned my blouse for him. He caressed my pussy lips. And after he had gotten me wet, he tasted me on his fingers. I invited him to help me orgasm. I guided him to caress my clitty with his fingertip, I got aroused but, being anxious, not enough to get over the edge. My breathing was fast and shallow. Between breathes I gasped, “Nibble my nipple, too!” As he did, the warmth finally surged through me, I moaned loudly, and my body convulsed. As he realized I was orgasming, his eyes opened wide in amazement. As I caught my breath and began to calm, I smiled and said, “That was wonderful!” It was the first time I was given an orgasm by another. I was so pleased he was the one to give it.
Then came mid-August and the time of my family's annual camping vacation trip. After much persuasion of my parents that I couldn’t go along because of my job and that I was capable of taking care of myself; I was allowed to stay home alone for two whole weeks. I was so happy, anticipating freedom.
The first night my parents and younger brother were gone, a Saturday, Rick and I went out for dinner like usual. But afterwards rather than to the darkness of a movie or to the privacy of his car, we went back to my house. I closed the drapes and turned the lighting low. I didn’t dare take him into my bedroom, which seemed evil, so we stayed in the living room. As we kissed and cuddled, we had soon partially undressed each other. He was left wearing only his boxers and I only my bra and bikini panty. I was so nervous.
I said I needed to go to the bathroom, and left him for a few minutes. I debated with myself, "How far would I go with him tonight?" I wanted more, more than before; but not so much that I risked losing control of myself. I calmed myself, and decided. I peed, flushed the toilet, and washed my pussy and my hands. I was so excited, with anticipation.
Rick was sitting on the edge of the sofa, watching me as I returned. His boxers were already tenting. I came and stood before him, between his spread knees. I unclasped my bra, letting it fall onto his lap. He looked up and smiled, then reached out and put his hands on either side of my waist. I put my hands atop his and gave a small push downwards. He understood and slipped his fingertips into the sides of my panty and slid it down off my tushy and hips. It fell to my ankles and I stepped free of it. He picked up both my panty and bra and tossed them aside. He leaned forward and gave me a symbolic peck of a kiss just above my mound. For the first time, I was fully naked before a man. I was so anxious.
I turned and sat beside him and we kissed deeply. He began to caress my bare breasts, but I interrupted and asked him to stand before me.
Awkwardly, I slipped his boxers off of him, at first getting the head of his cock caught in the waistband; but I took hold of it and set him free, and then pushed his boxers to the floor. He stepped out of them. For the first time, I saw a fully naked man. I was so aroused.
As he stood before me, I took his cock into my two hands and I began to kiss and lick it. When I saw his pre-cum, for the first time, I took the end of his cock right into my mouth and suckled the head of it while tonguing the tip. He began to stroke into my mouth. I let him, but kept one hand at the base of his shaft and restrained him to limit the speed and depth. My other hand cupped his bag-of-balls in my palm. I took in about half of his length, and he filled much of my mouth but not so deep as to gag me. Soon he asked, almost politely, "I'm going to cum, Syl. Do you, or do you not, want me to cum in your mouth?"
I slid my face back up his cock, just keeping my lips around the ring of the head, and nodded, "Yes." A couple of more strokes, and he erupted. I gagged, swallowed some, spit some, his cum filling my mouth and saturating my taste buds. It was the first time anyone had come in my mouth. I felt so sluttish, but excited.
I rushed to get a cloth to clean up the mess from my spitting. It would be horrible if my family found out. After thoroughly wiping up all his spilled cum, I smiled then kissed him deeply on his mouth, knowing he would taste himself on my tongue just as I still did.
Then he said he wanted to return the favor. Eager to experience ‘cunni’ for the first time, I offered my pussy to his tongue by sliding my tushy to the front edge of the sofa, leaning back onto my elbows, and opening my knees. He knelt before me and put his forearms on my inner thighs holding my legs spread.
Then he leaned in and kissed my mound. I softly sighed my approval. He lowered his face and kissed my pussy lips. I sighed a little louder. Then he licked upwards, between my outer lips. I moaned. He licked again, with a little more pressure, forcing between my inner lips. His tongue found I was wet inside and it glided along easily. The feeling was wonderful. His thumbs held me open as he lapped up my joy juice.
I was aroused but too anxious to orgasm. Although I even caressed my breasts and played my nipples, as I sometimes do when I ‘jill’ myself, I was unable to get over the edge to an orgasm. After a while, my hands lifted his face from my pussy.
He sat back with a sad look on his face. He realized I hadn’t orgasmed. I was sure he thought he had failed me. Trying to encourage him and not hurt his feelings any further; I said, "I was enjoying that a lot, a whole lot. But I guess I am still too apprehensive to orgasm that way.”
I continued, "Together, we need to learn to pleasure me well this way. Let's try again tomorrow. I’ll coach you to what feels good to me. Okay?"
He smiled meekly and replied, "Okay, please teach me what you would like. I want to learn how to make it enjoyable for you. I love you and never want to disappoint you again." I smiled. Although frustrated, I felt alright. I loved him and felt loved by him. We cuddled and kissed and fell asleep lying naked together on the sofa. Eventually we awoke and it was time to for him to leave.
After he left, I went right to bed and while thinking of him ‘jilled’ myself. I well knew how to finger myself to an orgasm and had a wonderful one. Then I fell asleep and dreamt of how much more exciting our eventual honeymoon would be. But waking in the morning, I worried if I actually had enough resolve to preserve my hymen until our honeymoon.
*
Epilogue:
We pleasured each other with ‘BJ’ and ‘cunni’ every night throughout my family's vacation away. I learned to take him deeper and to swallow without gagging and spitting. I also learned to be less anxious as he went down on me. He too got much better and learned to patiently kiss, lick, and suckle me to an orgasm. By the end of the two weeks which my family was away, we were both enjoying giving and receiving oral pleasure with each other very much.
We dated for another year, all through my senior year and the summer thereafter. I loved him and expected we would eventually get engaged and then married. But unfortunately, it became necessary for him to transfer from the local college to that university across the state. Meanwhile, I enrolled as a freshman at the local college. Although we visited twice his first semester away, with busyness and inconvenience we drifted apart. My heart was broken with disappointment, yet I still loved him.
I sometimes wonder what might have happened if I had been able to enroll instead at that university. Probably, I would have eventually become his wife and the mother of his children.
But instead, as you may have guessed, at the university he reconnected with Kathy. Now they are married and have two young children. I hope their lives are sensual, and not staid conservative traditional Christian lives like all of our parents. I have not seen either of them for several years, but wish them well. Occasionally I see, via some mutual friends, some Facebook news of them.
After Rick, through my college years and after; I dated many more men. I had my heart badly broken once more. Finally found a man worth marrying. So, I did. I am now twenty-nine and have happily been Ron’s wife for over three years.
Post Script:
This story is a reminiscence of things which happened a dozen years ago. Some Lush chat friends had asked to hear more about it, so this was written primarily to them. It is mostly true, but slightly embellished with just a little what-might-have-been fantasy.
The summer before my senior year in high school, I was seventeen and already had my driver's license, but no car of my own. I had just gotten my first real job, working part-time in the snack shop of the summer swim club where my family belonged. The swim club was at the edge of the sub-division where we lived. I usually walked there and back, about fifteen minutes each way.
There was a guy named Rick who worked there, as a lifeguard and swimming instructor, who I crushed on. He was two years older than me, and had completed one year of college. He had previously gone to my high-school and I remembered noticing him back when I was a sophomore and he was a senior. Because he sometimes came up to the snack shop and talked to me, with a hint of affectionate innuendo, I had hoped he might like me too. He seemed like a nice guy. My parents knew his parents. They had all gone to high-school together. So, I knew he, like me, came from a conservative traditional Christian family.
Yes, I came from a conservative family. I was a good girl, mostly. And, I was trying to keep that reputation. I fully intended to preserve my hymen as a gift to give my husband on our wedding night, remaining a virgin for him, at least technically. But, although still kind of naïve, I wasn’t as innocent as everybody thought. I looked at some ‘porny’ pictures on the computer from time to time. I ‘jilled’ myself to an orgasm many nights. And the previous summer, when I was sixteen, while away on a mid-August family camping vacation, travelling where no one knew me, I had explored some curiosities.
That previous summer, I had impulsively joined other teens my age in an I‘ll-Show-You-If-You’ll-Show-Me gambling game. So, I had already seen three guy's unzipped cocks. I had also seen one of those guys rather proudly 'jack' himself, and had been amazed to watch him spurt his cum. I had shown my breasts and even let myself be seen playing my nipples with my fingertips, pinching and twisting and tugging them. The other girl had let each of the guys kiss her bare nipples, which she seemed to like although she blushed a lot. But no one had yet seen, or touched, my pussy. I had quit the game before that happened. Scared, the other girl and I had fled the game when the cards required us to bare and touch each other’s pussy.
Later, as I fell asleep for the night, I was already regretting having abandoned the game. I had forfeited my first opportunity to touch a guy's cock. I 'jilled' myself to sleep and dreamt of holding one of those guy's cock in each of my hands as I kissed the tip of the third guy’s cock.
The next morning I considered if I might seek out one of those guys and offer to show my pussy in exchange for touching his cock. But I didn’t. My timidity exceeded my eagerness. My good girl self just couldn’t bring myself to actually proposition a guy like that. Then soon the vacation was over and it was time to go back home. The opportunity had passed.
But now, an early June day of the following year, back at the swim club, a children's swimming lesson had just finished. I was walking on my way to the snack shop past the area where parents observed the lessons. Rick had just started talking there to a pretty girl a little older than me, who I never remembered seeing before. And his swim suit was starting to swell. I was instantly jealous. Quickly I turned my eyes from Rick, who smiled as I passed by, and I looked at that girl and gave her a nasty frown. "Why," I thought, "had she intruded?" At once I realized I really wanted Rick. This desire of mine wasn't just a mere a fantasy crush anymore. I really wanted to be his. I was so mad.
A half hour later, that girl came up to the snack shop window and said she wanted to talk to me. I was still mad and didn’t really want to talk but, trying to be nice, did so anyway. Soon I was glad I had. She introduced herself as Kathy. She was the older sister of one of the girls in the swimming lesson and had just happened that day, instead of their mom, to drive her sister there. I was feeling a little less mad.
Kathy said, "You really like Rick, don't you? I could see your envy of me in your eyes. Please don't be jealous. He and I were in the same circle of friends when in high-school and we were just catching up, because we go to different schools now. He goes to the local college, but I go to the university across the state. I have my own steady boyfriend from there."
"Syl," Kathy confided softly, "Rick said his college girlfriend is away for the summer. So, I think he is available; at least for the summer, and maybe beyond. But, he will have a new summer girlfriend soon. And, unless you do something about it, she won't be you."
Kathy continued, "I think he likes you, Syl. I saw how he looked at you. It was the look of affection, tinged with desire. But maybe he is reluctant to approach you. He probably thinks that you think that he is too old for you; after all, he is in college but you are still in high-school. But, he is worth catching, and if you wish to pursue him, I will gladly help you."
I was stunned into silence, but gave her a huge smile, then started to giggle. Then, she did too. I was feeling better. "Um, yes Kathy. That would be great. Do you really think I have a chance with him?" I was feeling hopeful.
"Seeing how he looks at you, definitely; but you got to beat the competition. Find ways to be alone with him which aren't formal dates. He will be more comfortable that way."
"How do I do that?"
"Well, maybe ask him for a ride home, like if it's dark or rainy, or even if it isn't. He will. And you will be together and away from others. It will get him more comfortable being alone with you. Plus, he won’t be with somebody else." As we finished talking, she said, “I’ll be bringing my little sister again tomorrow and we can talk more then.”
Well, I did it. I asked him for a ride home that very evening. And even though I had to wait until his shift was finished, Rick gladly brought me home.
On the way to my house, Rick said he had seen me talking to Kathy. He explained she was just a very good friend from high-school and although they both liked each other a lot they had never dated, because they were never both unattached at the same time. We got to my house quickly, but then we sat and talked in his car for several more minutes. When I went into the house, my mom asked, "Whose car was that you got out of?" When I told her it was Rick who had brought me home from work she said, "Oh, he comes from a nice family. Just tell him I want him to drive extra carefully when you are with him."
The next day I saw Kathy again. She was happy I had taken her suggestion. She then recommended, "Tonight, tell him you haven't eaten a good meal all day, and ask him to stop somewhere on the way home so you can get something. If he offers to buy, it’s almost like a date; and he is really liking being with you."
Well, I did, and he bought us both hamburgers. We sat across from each other in the booth, talking easily and smiling a lot. Soon that became our daily after-work routine, even on weekend evenings. Well, if his college girlfriend was gone for the summer; I was starting to take her place.
Then one evening going to the restaurant after work, it started to rain. Rushing across the parking lot from his car, he slowed to reach back and encourage me along. I reached forward and took his hand. He gave me a surprised smile and then squeezed my hand. We ran through the rain hand-in-hand. That night he sat beside me, rather than across from me, in the booth. And he asked me out on a real date to a movie. I accepted immediately, eagerly. That night when he dropped me off at home we hugged and kissed deeply. As his tongue danced with mine, his palm cupped my breast through my tee-shirt. It was the first time a guy had done that for me. I was so happy.
A few days later in the darkness of the movie theatre, we sat close together, held hands, and kissed occasionally. After a while, he put his right arm around my neck and shoulder and draped his hand onto my Henley shirt and right breast. I crossed my left hand up to briefly pat his, gently acknowledging his touch but not pushing his hand away from my breast. Then, I twisted slightly towards him, leaned my head against his shoulder, and moved my other hand onto the top of his thigh. His free hand then guided my hand to the crotch of his pants. Nervously, I let it lie there mostly still on his bulge, but my curious thumb softly stroked along the ridge. I was anxiously excited. I kissed his neck; with his left hand he then reached across and opened the two remaining buttons of my Henley. When I didn't object, the fingertips of his right hand slipped inside my loosened Henley and caressed my breast and nipple through my thin sheer bra. My nipple swelled as I enjoyed his light touch. I don't remember the movie.
Afterwards, we went to a nicer restaurant for dessert where another of his classmates was waitressing. He actually introduced me to her as his girlfriend. She smiled to me and said, "You're a lucky girl!" I was so thrilled.
A few days later we both had the day off work and so we went to an early matinee movie. I had planned my wardrobe better. I wore a fully front-buttoned blouse, and a bra with a front clasp which I had purposely bought for him. Again sitting beside me, he put his arm around my shoulder and draped his hand onto my blouse and breast. Again, I gently patted my approval. Then, I turned towards him, rested my head on his shoulder, moved my hand onto his thigh and, as I hoped, he again guided it to his cock. Tentatively, I caressed him, softly rubbing my whole palm along his bulge in his pants. I kissed his neck; he unbuttoned three more buttons of my blouse. I softly moaned my approval as he slipped his fingers inside my loosened blouse and under my bra, and caressed my breast. He gently scissored my nipple between two of his fingers.
Following the movie we went for a nice dinner. As we had our dessert, the sun set. Leaving the restaurant, he drove us to an obscure little park overlooking a small river. Our car was the only one in the small parking lot. As we sat and talked together in the front seat, we began cuddling each other. Still acting the timid good girl, I nonetheless acquiesced to letting him unbutton most of the buttons of my blouse, and let him caress my breasts and nipples through my bra. He again guided my hand to the crotch of his pants, and I discovered he had surreptitiously unzipped and his cock was standing tall and free. My hand gently explored it. In turn, my other hand unclasped my bra, letting it fall open. He cupped my bared breast in his palm and thumbed my nipple. We kissed deeply as we fondled one another. I was so happy.
On the Fourth of July holiday, Rick asked me to go steady with him. Hesitating for just a moment, I quickly debated with myself in my head. I fully realized going steady meant others would presume we were petting each other on our dates. “How would that effect my reputation?” I wondered. Yet some girls who went steady were still perceived to be nice girls in nice relationships with nice guys. “Maybe, I could be too and all would be okay,” I thought. “After all, he was one of those nice guys. He always treated me well, both publicly and privately; and I was falling in love with him.” I didn't want to risk losing him by declining. And, because he was willing to commit to being exclusively mine, I happily accepted.
So we exchanged class rings. As fashion required, I wore Rick's ring on a gold chain hanging from my neck into my cleavage, near my heart. My dad was not pleased I had chosen to go steady, but he didn't object either. I don't think he actually disliked Rick but was probably just afraid his only daughter was growing up too soon, and too fast. My Mom however was pleased I had found a nice guy from a nice family. I think she secretly liked Rick, who may have reminded her of a younger version of my Dad. Years later I learned my Mom had persuaded my Dad it was okay I was going steady with Rick, and if he objected he risked harming his relationship with me.
Since we were going steady now, we began to pet more intimately on our dates. He suckled my bared breasts and reached up my skirt and caressed me through my panty. I stroked his unzipped cock. Sometimes I took just the very tip of him to my closed but pursed lips, smearing his precum onto my lips to then lick and taste with my tongue. But, still trying to be the good girl, I didn’t let him enter my mouth and I didn’t directly touch his cock with my tongue either. But I loved seeing him erupt for me as I stroked and twisted him. I was so happy.
Although, I let him reach up my skirt and caress me through my thin panty, I hadn't yet let him take it off. One time he pushed my panty's crotch fabric aside and directly touched my lips. I gasped in surprise and pleasure. He seemed frightened and pulled back. But smiling, I soothingly said, "It’s okay. I was just surprised. I liked it. But please don’t ever go inside my ‘gina. I am preserving my hymen for our wedding night." He respected that, and just caressed my lips and rubbed my hooded clitty. It was new and arousing. I was so happy.
The next time he fingered me, as he parted my lips slightly but hadn’t quite yet entered my 'gina, I cautioned him not to go deeper. He replied, "Syl sweety, I'm not going to tear your hymen. I just wanted to get some of your joy juice from between your lips onto my finger to taste. You smell so good that I want to taste you too." Then he smiled, and lifted his finger to his lips and licked it, saying, "Mmmm, you taste delicious!"
He was a patient man of his word. Subsequent dates his fingers rubbed me along my mound and pussy, parting my outer lips and circling between my inner and outer lips, sometimes hooking under my hood to touch my clitty, and continued to finger up my wetness between my inner lips from the entry to my 'gina; but he did not try to penetrate me any deeper. And it seemed, he always wanted to taste my joy juice.
One time, after I had stroked him to eruption, he wiped up some of his cum on his finger and offered it to my lips. I sniffed its aroma up close and was intrigued. Tentatively, the tip of my tongue, having a mind of its own, reached out and touched his cum covered finger. He tasted good. My tongue then licked his cum from his finger. We smiled at each other.
When he next offered me his cum wet finger; I again sniffed it, and then touched it with the tip of my tongue. But then, my mouth and tongue went on to fully suckle his finger. I was hooked by the taste of him. Although I was too timid to suck his cock, I was at least going to 'BJ' his cum covered finger and enjoy the taste of him.
Then came late July, and Kathy invited me and Rick to double-date with her and her steady boyfriend, Doug. One Saturday, we travelled across the state to the university, which they both attended, to go to a concert at an auditorium there. Doug borrowed his Dad's full-size car for the road trip, with Doug and Rick sharing the driving. Because he knew where we were going, Doug drove going there but Rick drove coming back. It was very long day, evening, and night. The concert was nice, but what I remember mostly was the ride home.
Traveling back home in the early morning, I listened to Kathy and Doug making out in the darkness of the back seat of the car. I was too embarrassed to turn around and look, it was too dark anyway; but listened intently. At times, I heard each of them moaning softly. I thought they had each, in turn, cum.
Kathy told me privately later, yes indeed, Doug had suckled her breast and finger fucked her pussy, bringing her to an orgasm. And, she had sucked Doug's cock, bringing him to a climax in her mouth. She said, "I love the taste of Doug's cum. I imagine Rick's tastes good too, doesn't it?"
Smilingly, I replied, "Yes he does taste good, very good!" Yet somewhat ashamed, I did not acknowledge I hadn't yet tasted his cum directly from his cock. And although I really wanted to know, I did not dare ask her if her hymen was still intact, afraid to maybe learn it wasn't anymore.
Kathy's comment confused and challenged my morality. Kathy was a nice girl, yet she had openly acknowledged she enjoyed sucking Doug’s cock and being finger fucked by him. But I had always thought good girls weren't supposed to do that, at least not until they were engaged. I was envious of her bold confidence to do as she wished. I wondered to myself, “Could I be that bold too and still be a good girl?”
"After all," I rationalized to myself, "I had fallen in love with Rick. He was so special to me. And, we would probably get engaged eventually anyway." I resolved to dare to be bolder with Rick.
The next time we went parking, when Rick again reached up my skirt, I took a deep breath, asked myself whether I was really sure if I wanted to be bolder with him. Then deciding I did, I invitingly whispered, "You may pull my panty down, but please don't harm my hymen." He then reached up with both hands and pulled it down, past the hem of my skirt to my knees. But wanting to open my knees for him, I pushed it down further to my ankles.
With a big smile, he just starred at my pussy. He said softly, “Syl, your pussy looks amazingly beautiful.” Then he slowly reached out and touched me there, watching himself as he did. Very quickly, I was very wet. Soon he was again tasting me upon his fingers. I was so aroused and felt compelled to let myself orgasm.
So, I spread my knees wider. I parted my lips, rubbed some of my wetness up to moisten my clitty, and circled the pad of my fingertip on my clitty. As he watched me, I 'jilled' myself. He was amazed to see my legs thrash and my back arch as I moaned with pleasure. It was the first time I wasn't alone when I orgasmed, and I was so pleased he was the first one to witness me.
After I calmed, I turned and licked all around the tip of his cock, and for the first time tasted his precum directly from his cock. I kissed the so soft skin of the head of it. But, I still didn’t take him into my mouth. He showed me the wrinkled spot on the underside of the head of it where I could make him cum just by patiently circling my moistened fingertip on it. I did so, until he spurted all over his stomach and chest. Before he offered it to me, I quickly wiped up some of his cum with my fingertip and tasted it. I loved his taste. “Why was I so timid to take him directly into my mouth?” I wondered.
When it was time to go, rather than pulling my panty up, I slipped it off over my shoes. I gave it to Rick as a memento. So that night I returned home pantyless under my skirt. It was the first time I went like that. It felt so naughty, but exciting.
A few days later, when we were again parking in his car, he once again reached up my skirt and removed my panty. I unbuttoned my blouse for him. He caressed my pussy lips. And after he had gotten me wet, he tasted me on his fingers. I invited him to help me orgasm. I guided him to caress my clitty with his fingertip, I got aroused but, being anxious, not enough to get over the edge. My breathing was fast and shallow. Between breathes I gasped, “Nibble my nipple, too!” As he did, the warmth finally surged through me, I moaned loudly, and my body convulsed. As he realized I was orgasming, his eyes opened wide in amazement. As I caught my breath and began to calm, I smiled and said, “That was wonderful!” It was the first time I was given an orgasm by another. I was so pleased he was the one to give it.
Then came mid-August and the time of my family's annual camping vacation trip. After much persuasion of my parents that I couldn’t go along because of my job and that I was capable of taking care of myself; I was allowed to stay home alone for two whole weeks. I was so happy, anticipating freedom.
The first night my parents and younger brother were gone, a Saturday, Rick and I went out for dinner like usual. But afterwards rather than to the darkness of a movie or to the privacy of his car, we went back to my house. I closed the drapes and turned the lighting low. I didn’t dare take him into my bedroom, which seemed evil, so we stayed in the living room. As we kissed and cuddled, we had soon partially undressed each other. He was left wearing only his boxers and I only my bra and bikini panty. I was so nervous.
I said I needed to go to the bathroom, and left him for a few minutes. I debated with myself, "How far would I go with him tonight?" I wanted more, more than before; but not so much that I risked losing control of myself. I calmed myself, and decided. I peed, flushed the toilet, and washed my pussy and my hands. I was so excited, with anticipation.
Rick was sitting on the edge of the sofa, watching me as I returned. His boxers were already tenting. I came and stood before him, between his spread knees. I unclasped my bra, letting it fall onto his lap. He looked up and smiled, then reached out and put his hands on either side of my waist. I put my hands atop his and gave a small push downwards. He understood and slipped his fingertips into the sides of my panty and slid it down off my tushy and hips. It fell to my ankles and I stepped free of it. He picked up both my panty and bra and tossed them aside. He leaned forward and gave me a symbolic peck of a kiss just above my mound. For the first time, I was fully naked before a man. I was so anxious.
I turned and sat beside him and we kissed deeply. He began to caress my bare breasts, but I interrupted and asked him to stand before me.
Awkwardly, I slipped his boxers off of him, at first getting the head of his cock caught in the waistband; but I took hold of it and set him free, and then pushed his boxers to the floor. He stepped out of them. For the first time, I saw a fully naked man. I was so aroused.
As he stood before me, I took his cock into my two hands and I began to kiss and lick it. When I saw his pre-cum, for the first time, I took the end of his cock right into my mouth and suckled the head of it while tonguing the tip. He began to stroke into my mouth. I let him, but kept one hand at the base of his shaft and restrained him to limit the speed and depth. My other hand cupped his bag-of-balls in my palm. I took in about half of his length, and he filled much of my mouth but not so deep as to gag me. Soon he asked, almost politely, "I'm going to cum, Syl. Do you, or do you not, want me to cum in your mouth?"
I slid my face back up his cock, just keeping my lips around the ring of the head, and nodded, "Yes." A couple of more strokes, and he erupted. I gagged, swallowed some, spit some, his cum filling my mouth and saturating my taste buds. It was the first time anyone had come in my mouth. I felt so sluttish, but excited.
I rushed to get a cloth to clean up the mess from my spitting. It would be horrible if my family found out. After thoroughly wiping up all his spilled cum, I smiled then kissed him deeply on his mouth, knowing he would taste himself on my tongue just as I still did.
Then he said he wanted to return the favor. Eager to experience ‘cunni’ for the first time, I offered my pussy to his tongue by sliding my tushy to the front edge of the sofa, leaning back onto my elbows, and opening my knees. He knelt before me and put his forearms on my inner thighs holding my legs spread.
Then he leaned in and kissed my mound. I softly sighed my approval. He lowered his face and kissed my pussy lips. I sighed a little louder. Then he licked upwards, between my outer lips. I moaned. He licked again, with a little more pressure, forcing between my inner lips. His tongue found I was wet inside and it glided along easily. The feeling was wonderful. His thumbs held me open as he lapped up my joy juice.
I was aroused but too anxious to orgasm. Although I even caressed my breasts and played my nipples, as I sometimes do when I ‘jill’ myself, I was unable to get over the edge to an orgasm. After a while, my hands lifted his face from my pussy.
He sat back with a sad look on his face. He realized I hadn’t orgasmed. I was sure he thought he had failed me. Trying to encourage him and not hurt his feelings any further; I said, "I was enjoying that a lot, a whole lot. But I guess I am still too apprehensive to orgasm that way.”
I continued, "Together, we need to learn to pleasure me well this way. Let's try again tomorrow. I’ll coach you to what feels good to me. Okay?"
He smiled meekly and replied, "Okay, please teach me what you would like. I want to learn how to make it enjoyable for you. I love you and never want to disappoint you again." I smiled. Although frustrated, I felt alright. I loved him and felt loved by him. We cuddled and kissed and fell asleep lying naked together on the sofa. Eventually we awoke and it was time to for him to leave.
After he left, I went right to bed and while thinking of him ‘jilled’ myself. I well knew how to finger myself to an orgasm and had a wonderful one. Then I fell asleep and dreamt of how much more exciting our eventual honeymoon would be. But waking in the morning, I worried if I actually had enough resolve to preserve my hymen until our honeymoon.
*
Epilogue:
We pleasured each other with ‘BJ’ and ‘cunni’ every night throughout my family's vacation away. I learned to take him deeper and to swallow without gagging and spitting. I also learned to be less anxious as he went down on me. He too got much better and learned to patiently kiss, lick, and suckle me to an orgasm. By the end of the two weeks which my family was away, we were both enjoying giving and receiving oral pleasure with each other very much.
We dated for another year, all through my senior year and the summer thereafter. I loved him and expected we would eventually get engaged and then married. But unfortunately, it became necessary for him to transfer from the local college to that university across the state. Meanwhile, I enrolled as a freshman at the local college. Although we visited twice his first semester away, with busyness and inconvenience we drifted apart. My heart was broken with disappointment, yet I still loved him.
I sometimes wonder what might have happened if I had been able to enroll instead at that university. Probably, I would have eventually become his wife and the mother of his children.
But instead, as you may have guessed, at the university he reconnected with Kathy. Now they are married and have two young children. I hope their lives are sensual, and not staid conservative traditional Christian lives like all of our parents. I have not seen either of them for several years, but wish them well. Occasionally I see, via some mutual friends, some Facebook news of them.
After Rick, through my college years and after; I dated many more men. I had my heart badly broken once more. Finally found a man worth marrying. So, I did. I am now twenty-nine and have happily been Ron’s wife for over three years.
Post Script:
This story is a reminiscence of things which happened a dozen years ago. Some Lush chat friends had asked to hear more about it, so this was written primarily to them. It is mostly true, but slightly embellished with just a little what-might-have-been fantasy.
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