Sissy Stepson 10 Stepmother s Sissy
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Meagan's First Step Into Womanhood free porn video
The last day of school had finally arrived. The last day of my junior year in high school was over. When I arrived home, there was more than the usual hustle and bustle. With the end of school, came the traditional two-week family vacation. Dad was already loading up the car, and mom was frantically scurrying around the house looking for last-minute odds and ends, marking off each item on her checklist. My family was organized if nothing else, and despite the apparent chaos, it was organized chaos.
This year was different for me though. Instead of being away from my friends and having to bend to the will of what everybody else wanted to do, I got to stay home. My mom wasn’t too happy about it. For her, the family was everything, and the family should be everything together. But for me, especially being a young 17-year-old woman, I found it increasingly confining. I needed time for myself, time to do what I wanted to do. This year that time had finally arrived. True, in a few hours I would begin my shift at the local diner and all that it entailed. But at the end of the day, I would be coming home to an empty house. No parents, no brothers, and sisters, nobody but my boyfriend and me. For possibly the first time in our young lives, we would be truly alone together. For once we would have time to ourselves. My heart skipped a beat because both of us already had plans for the two weeks ahead. A small smile formed on my lips at the thought of the liberty that represented for me.
Being the first day for school vacation the diner was quite busy. Many of my schoolmates were there as well as large numbers of families stopping in for lunch. I was kept busy which on looking back was a blessing. It kept me from thinking about Ryan and me tonight. We had been waiting for this moment for what seemed like forever. Tonight was the night. Tonight I would finally pass from being a 17-year-old girl into becoming a young woman.
Finally, at the end of my shift, I was able to hurry home and get ready. Ryan would be picking me for a romantic dinner at what passed for an upscale restaurant in these parts some twenty-five miles away. At least no one, hopefully, would know us and report back to my parents. Ryan at nineteen was older than me. He had graduated from high school two years ago. Mom had never like Ryan. In reality, mom didn’t like me to hang around boys. Mom wanted to keep me as her little girl forever. She hated to admit that I was growing up. If only she knew how much I was going to grow up tonight!
Getting home I immediately got out of my work uniform and showered before heading to my bedroom to get dressed. As I got dressed, I'll admit I was getting more than a bit nervous and apprehensive. Ryan had told me that he'd already had intercourse. I’m smart enough to know that in our little town, the boys didn’t have much opportunity, but there were several girls who everyone knew 'put out'. Ryan never told me who he'd been with and to be honest, I didn’t really want to know. But I was sure that Ryan had been with one or the other loose girls at high school while he was there.
We started dating in my sophomore year; at least we called it dating. As I mentioned, mom didn’t want me hanging around boys. But I was able to spend time with Ryan at school and at sports games and other school events. If you found me at school, you found Ryan – at least until he'd graduated. After he graduated, it became harder to be with him, but when he could, he would hang around the diner where I worked.
Ryan had introduced me to the beginnings of sex when I was sixteen. Beginning with passionate kissing, we'd graduated to the caressing of my breasts and heavy petting through my jeans and panties, and likewise, he'd introduced me to his penis and more recently to blow jobs. It had been difficult, and there was always the underlying fear on my part that my parents, my mother especially, would discover us. The thought terrified me!
There was one more thing that scared me a bit too. During my first visit to a gynecologist, it was discovered that I had an extraordinarily thick hymen. The doctor had said it didn’t represent a health issue but that when I started to become sexually active, intercourse, especially early intercourse, would probably be somewhat painful and difficult. She'd said that she could surgically cut the hymen, but of course, my mother was not about to consider that. She was uncomfortable enough that I'd begun having periods because she knew that I was starting to blossom into a young woman. She didn’t say it and never mention it me, but I also think mom had a kind of puritanical view of sex anyways. Perhaps she was hoping that I wouldn’t discover sexual pleasure until marriage. If so, she was going to be disappointed!
Being summer, I dressed appropriately. Anything sexy was out of the question! Mom would never have approved of anything that hinted of sex or was too revealing. Before going into the shower, I'd laid out my clothes for the evening---A beige, flowered-print, sleeveless summer dress, white cotton bikini panties and a bra of similar color and material. I'd also laid out a pair of suntan thigh high nylons. I'd never worn anything like them before – the few times that I had to wear nylons, mom had purchased pantyhose for me. I definitely wasn’t wearing those tonight! A few weeks earlier, I asked an older girlfriend from school pick up some thigh highs at the local Walmart. I had carefully hidden them from my mom’s prying eyes. The feeling as I rolled them up my legs was incredible. I felt so sexy, perhaps for the very first time! After putting on my underwear, nylons and slipping my dress over my head, I slid my feet in my white high heels. I glanced at my watch---it was already 6:35. Ryan would be here in ten minutes. I put on a pair of pearl earrings and a matching necklace. Taking a deep breath and checking myself out in the mirror, I was ready!
At 6:45 precisely, Ryan was at the front door. After a brief kiss and some quick pleasantries, he escorted me to his car, opening the door for me before getting into the drivers’ seat. The restaurant was about 30-35 minutes away, and we had a 7:45 reservation.
The restaurant was served German food. The ambiance was undoubtedly romantic. Each table had a colored globe-encased candle burning on it. The background lighting was subdued. It invited budding sexual desires to increase in intensity.
I'll admit my mind wasn’t on the food! It was on what was planned for later in the evening. I wanted to do this. I had wanted to do it for some time now. Unfortunately, we never had the opportunity to be alone. Now that the house was empty and mine, I was anxious to get home. I was eager to be alone with Ryan. I wanted Ryan, and I knew he wanted me. My hormones were raging, and I could feel my pussy beginning to tingle with desire and could feel the dampness seeping into my panties. I was aching to feel a cock in me- Ryan’s cock. When the waitress came to ask about dessert, I nudged Ryan.
“Let’s have dessert at home Ryan.”
Ryan smiled back at me and told the waitress, “No thanks. Can we please have the check?”
After quickly paying the bill, Ryan led me by the hand back to the car. On the trip back to my house, Ryan took my hand and squeezing it, asked me,
“Meg, are you certain you want to do this? I mean I’m not going to be disappointed if you want to wait. I’ll understand. I want your first time to be when you’re truly ready for it. I want everything to be perfect for you, not just for me.”
I returned Ryan’s squeeze and gazing longingly into his eyes, replied,
“Ryan, I’ve never wanted anything else in my life as much as I want this. I’ve been ready for this moment for a long time. I want you to take my virginity, Ryan. I want you to be my first. I want to feel your cock inside of me to take my virginity and fuck me.”
I hesitated for just a moment then added, “Please.”
I have to admit, I was nervous and more than a little afraid. I was scared of getting pregnant. I knew that Ryan had gotten condoms. After all, he was nineteen. That was one benefit of having an older boyfriend! But still, there was that underlying fear.
I was afraid that my parents would find out. Even worse, I worried that my parents would, for whatever reason, come home unexpectedly and walk in on Ryan and me in our moment of passion. I struggled to put that possibility out of my mind. This is MY night I told myself.
I was also afraid that Ryan would be disappointed. I had told Ryan about my hymen and had said to me, “Meg, I’ll gentle. It'll be okay. I promise. I won’t hurt you, Meg. I care too much about you to hurt you!”
I replied, “I know, Ryan. But the doctor said it would be somewhat painful my first time.”
“I know, Meg. If it hurts, I’ll make sure it is a good hurt. I promise.” he said again.
My heart began to beat faster as we pulled on the street where my house was located. When the car pulled into the driveway, I thought it was ready to leap out of my chest.
Ryan could sense my nervousness and apprehension. He had been holding my hand the whole ride home. Now he squeezed it gently again and said,
“Meg, it will be all right. Don’t be scared.”
“I know,” I replied. “I can’t help it; I’m still a little scared.”
Ryan leaned over and kissed me gently again.
“Are you sure Meg? I don’t want you to do anything you don’t want to do or aren’t ready for.”
I returned his kiss.
“Yes, Ryan. I’m sure. I want to do this, and I’m ready to do this. Let’s go in.”
Ryan opened my door and helped me out of the car. I walked ahead of him and could imagine him looking at my longish (even then) legs and watching the wiggle of my ass as I walked up the stairs of the front porch. Taking the keys from my purse, I opened the door, and Ryan followed me in. It took a minute or so, but I was able to turn on the lamp at one end of the couch in the living room. Taking a deep breath, I moved toward Ryan. I grabbed his hands and pulled him to me. Looking deep into his eyes, our lips moved toward each other’s.
I had been kissing Ryan for several years. It had been pleasurable, but it had never been this electrifying before. As our lips met, I could feel the release of sexual energy, a sexual desire that I had never experienced before. My body quivered with excited anticipation. Ryan could feel my body’s response and pulled me tightly into him as our kisses quickly became more passionate. It wasn’t long before we were on the couch.
There, our kissing escalated. His tongue in my mouth, mine in his. Our tongues were twirling around each other’s. Our sexual passions, desires, and temperatures were quickly rising beyond the boiling point. We wanted each other. Our bodies told us. Our minds told us.
Nervous, I 'accidentally' lowered my hand to his crotch. I could feel Ryan’s cock quiver through his pants at my touch. I knew more than ever what I wanted.
“I want you to fuck me, Ryan,” I whispered in his ear before resuming our passionate and now unbridled kissing.
Ryan responded, “I will, Meg, I will.”
With those words, Ryan tentatively lowered his hand to my knees and squeezed them uncertainly.
I took a deep breath and gasped lightly. I reached down and began to move his hand upward, at the same time raising the hem of my dress. My breathing was quickening. My sexual temperature was rising rapidly in response to our kisses and his touches. My pussy was warm, tingling and wet. My panties were getting quite moist, and the scent was beginning to fill the room.
I moved my hand back to Ryan’s trousers and began tracing the outline of his erect cock through the material. Uncertainty, I moved to his zipper. Ryan sighed and let out a faint moan of approval.
“Don’t stop, Meg, unzip me,” he said.
I'd seen Ryan’s cock before. But this time was different. This time, sucking his cock was not going to be the end of the program. This time, it was going to be the beginning!
Nervously, I began to pull the zipper down. Then, reaching up to his waist, I began to unbuckle Ryan’s belt. Ryan gasped with approval again. After unzipping him and unfastening his belt, Ryan reached down and worked his suit trousers down. His shorts quickly followed revealing the prize that I been seeking, and that was now mine.
My eyes looked into his, as I slowly lowered my mouth to his waiting cock. It twitched uncontrollably in my hands as my tongue touched its tip. A soft groan and sigh escape from Ryan as he leaned back into the couch and then began to runs his fingers through my auburn hair.
As my tongue swirled around the tip, I began stroking the shaft through my fingers. Ryan’s moans and groans were increasing now.
Tracing his fingers through my hair, he began to guide my head downward. I eagerly swallowed as much of his cock as I could. After all, while this was not my first blowjob, I certainly had not had much opportunity to practice. I was still pretty inexperienced at the art of fellatio. Ryan didn’t seem to mind.
“This it, Meg,” Ryan moaned softly. “That feels so good.”
His cock was throbbing in my mouth. I removed my lips and began to stroke the tip with my clenched fingers while moving my lips down to his shaft. I started nibbling on it. Ryan bucked up unexpectedly as his moans and groans got more vocal.
I wasn’t sure how more Ryan could take. After all, he wasn’t all that much more experienced than I was. I didn’t want to ruin the evening by having him explode before I had the opportunity of feeling his cock in my pussy.
I moved my lips back to the tip and sucked his cock for a few more moments before stopping and moving my head back up.
“Ryan,” I said, “Will you unzip me honey?” as I turned my back to him. My breathing quickened as I felt the zipper being slowly lowered.
“Could you unclasp my bra too?” I added. I twitched uncontrollably as I felt Ryan’s fingers fumble with the clasp.
Standing up, I began to pull my dress up over my head. Ryan’s eyes were open so wide. Never before had he seen my body. At least not like this! He eagerly watched as I continued to pull the hem of my dress higher and higher. The tops of my thigh-highs quickly came into view and just a moment later, my panties. Lifting each leg in turn, I removed my heels.
I heard a soft “yes” escape from Ryan’s mouth.
Holding my dress in one hand, I pulled the straps of my bra off each shoulder, revealing my small, B-cup, breasts.
Ryan instinctively reached up and began to caress my breasts. He kneaded the nipples between his fingers for a moment before moving his mouth to each one.
I gasped at his touch. My nipples were erect and so sensitive. I tilted my head back and began to moan softly in appreciation.
“That feels so good, Ryan,” I said. “Please, don’t stop.”
He continued suckling my breasts for a minute or so before I pushed him away.
“Want to go to my bedroom?” I asked innocently, holding out my hand. Stupid question I immediately thought to myself.
“Yes,” Ryan responded, his voice hinting at his uncertainty. I’m sure he was just as apprehensive and nervous as I was.
Ryan took my hand, and I led him into my bedroom. I tossed my dress and bra onto a chair in the corner of the room.
“Here’s my bed,” I said, pointing to the double bed in the center of the room.
“Nice,” Ryan responded.
It seemed like we were frozen in time. Both of us were just standing there like the scared teenagers we were. It was evident that someone was going to have to make the next move.
Grabbing Ryan’s hand, I sat down on the edge of the bed, pulled him down beside me.
“Are you scared, Ryan?” I asked nervously.
“Yes,” he replied, just as nervously.
Squeezing his hand, “Me too,” I told him. “But I really want this Ryan. I want you to be my first. I want you to take my virginity. I want your cock in me,” and after a moment of silence, added, “Please.”
Ryan looked into my eyes. I could tell he wanted my cherry as much as I wanted him to pop it. Our lips moved closer together to resume our kissing. Soon, both of us were lying back on the bed, holding each other and kissing each other passionately and without abandon.
A few minutes later, I managed to blurt out,
“Ryan, take your clothes off for me.” It didn’t take him long to comply, tossing his trousers, shirt, tie and underwear on the chair with my dress and bra.
Suddenly, I could feel Ryan’s hand moving downwards towards my waist. I gasped loudly as he slipped his hand under the waistband my panties and down to my vulva. I instinctively lurched upwards at his touch. He began palming my pussy. I started moaning uncontrollably in response.
Everything was happening more quickly now. Moments later, Ryan broke our kiss. Sitting up, he looked deep into my eyes to judge my reaction as he began moving his other hand downwards.
Moments later, Ryan’s fingers slipped under the waistband my panties. My breathing quickened. There was no going back now I briefly thought to myself. I lifted my hips off my bed as Ryan slowly pulled my panties down my legs and tossed them on the floor. He then moved the palm of his hand back to my vulva.
At the same time, I moved my hand back to Ryan’s erect penis. Grabbing it, I began stroking it again between my fingers before starting to move my mouth back to it. Ryan gasped loudly as I took him back into my mouth. As I began sucking Ryan, he was heavily petting and caressing my wet pussy. Both of us were wiggling uncontrollably as our raging hormones were taking over and guiding us.
Suddenly, Ryan sat up and repositioned himself so that his head was down towards my sex. Opening my legs slightly with his hands, I felt his mouth on my pussy! I leaped upwards uncontrollable as the feeling of his tongue sent shivers through my body. I struggled to concentrate on sucking Ryan as he began eating out my pussy with fervor. My movements were becoming wild and uncontrollable as I was moaning and groaning loudly now.
“Oh my God! Yes, OH YES!” I screamed out as Ryan’s mouth began taking me further than I had ever been. My pussy was dripping with juice which Ryan was eagerly and passionately lapping up.
I felt a then unfamiliar tension building inside of me. Trying desperately to speak, I finally managed to get out, “Ryan, FUCK ME! Fuck me now!”
Both of us were breathing heavily, almost out of breath. Ryan sat up and moved to his pants that had been tossed on the chair. Getting his wallet, he took out a foil package containing the condom.
I bit my lip in eager anticipation of what would be coming soon.
I watched attentively as Ryan opened the package and rolled the condom onto his fully erect cock. As Ryan moved back to the bed, I instinctively spread my legs.
Ryan lowered his head to my pussy and lapped it a few times before taking some of its juices and rubbing them on the tip of his cock. He crawled on the bed and moved between my legs, forcing me to spread wider and giving him access to my pussy.
I bucked up uncontrollably as I felt him rub his cock up and down my wet slit. My breathing was rapid and heavy now; my heart felt like it was going to explode.
Suddenly, without warning, Ryan thrust forward.
I screamed out “OOOUUUCCCHHH” as he entered me for the first time. Although I had told Ryan about my hymen and I been told my first time would hurt me, he was startled at my response.“I’m sorry, Meg,” Ryan blurted out.
“Its okay baby,” I gasped in reply. “Just give a moment,” I added.
Taking some deep breaths, I told Ryan, “I’m ready.”
Ryan crawled between my legs and placed his cock back at the entrance to my pussy and entered me again.”
I groaned, “Ooouuuccchhh,” again.
“Do you want me to stop?” Ryan gasped.
“NO!” in gasped in return. “Fuck me.”
Ryan slowly fed the entire length of his cock into me. I grabbed the bedsheets as I struggled to come to terms with the pain I was experiencing and the fullness I was feeling inside me for the first time.
Slowly, Ryan began fucking me. It hurt as his cock continued to wear away the thick hymenal ring.
Although it was hurting, it also felt so good. After a few minutes, the pleasure of being fucked outweighed the discomfort I was still feeling from the remnants of my hymen.
Soft moans and “Yesses” escaped from lips as I began raising my hips to meet Ryan’s slow, steady thrusts in me. I couldn’t believe how good his cock felt in me. I never wanted it to end! It felt so good.
As Ryan slowly fucked me, I could feel a familiar yet unfamiliar tension building inside of me. My breathing quickened, my heart was pounding hard. My moans and groans increased in frequency and intensity. I was fighting to stay in control but couldn’t.
Ryan could sense me release and began thrusting faster and harder.
My moans and whimpers of pleasure were interspersed with the frequent if irregular “ouches” that were still escaping from my mouth as Ryan’s cock continued to wear away my hymen.
Without warning, I screamed out “YES! OH YES, YESSS,” as I bucked upwards. My body quivered uncontrollably as I experienced my first ever orgasm.
At the same time, Ryan, who had been on the verge of cumming since we had been on the couch, erupted in a loud “AAARRGGGHHH” as he thrust violently forward into me before exploding uncontrollably.
Both of us laid on the bed for several minutes as our bodies gradually returned to normal. We were covered in sweat. Our hands stroked each other’s chests and arms and hair as our breathing and heart rate returned to normal.
“You were great, Meg,” Ryan said, stroking my hair and kissing me gently.
“You were too, Ryan,” I said, returning his kiss. “I guess we should get cleaned up, shouldn’t we?” I added.
“Yes, I guess we should.”
After showering, I put on just a pair of clean panties and waited on my bed for Ryan to emerge from his shower.
Ryan moved to the chair to begin putting his clothes back on.
“What are you doing, Ryan?” I asked innocently. “Why don’t you stay here with me tonight?” I said, patting my bed.
Ryan put his pants back on the chair and sat down next to me?
“Really?” he asked, wondering if I was just teasing him.
“Really,” I replied. “After all, you’re not the kind of boy who would just fuck a girl and run are you?” I continued teasingly.
“NO, I’m not,” Ryan replied as he kissed me again.
I always remembered my first time vividly. The combination of desires, of all the senses, the feelings and yes, even the pain, always stayed with me. As I got older, I more and more wanted to relive that experience. It happened nine years later.
Edited by ChrisM
Lizbeth
- 04.07.2022
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- Category:
- First Time
