tagAnalHS Sweetheart Ch. 04

HS Sweetheart Ch. 04

bypainter0987©

This is the fourth in a multi-part story about my early experiences with sex. For complete background, see the previous sections of the story. While these ‘HS Sweetheart’ stories are mostly true, I have changed names to protect the not-so-innocent. Please vote if you liked or didn’t like the story and send some feedback.

My memories of the spring of my senior year of high school are mostly filled with Mary Jane. I’m sure that I was deciding where I wanted to go to college and setting up plans for summer jobs, but all I remember is Mary Jane. Mary Jane started off the year, as she had for the past five or six years, as the object of my adolescent fantasies and dreams. Through some stroke of luck or divine blessing, her romantic attention finally turned my way. We started dating coincidentally around her eighteenth birthday in March, and as I’ve described, within weeks she had taught me almost everything there is to know about sex. I’ve since discovered that not all women hide within themselves sexual deviants just waiting for a chance to talk dirty and experience anything and everything sexual, but at the time that is exactly what I had.

Mary Jane didn’t just love sex, she WAS sex. When she walked into a room, people looked at her and could feel it. I saw it happen to men and to women. First their eyes would linger just a little longer than necessary and Mary Jane’s figure. Then they would return their gaze to scan up and down her body a few times. I could always see their features soften a little bit as the stress from whatever was on their minds melted away at the presence of the vixen standing near them. The last step was always the biggest turn on. No matter how old or what gender, as long as they were old enough to be thinking about sex at all, all people given enough exposure to Mary Jane, would start to fantasize. I would watch as their mouths relaxed and tongues came out to lick their lips. Depending on the weather I would watch nipples harden on women’s breasts and bulges grow in men’s pants. Watching it all made my own dick stiffen slightly. Even if these people weren’t turned on by her in particular, she made everyone around her think of sex.

Of course, for me thinking of sex and thinking of her were one and the same. As soon as I saw her 38-24-34 hourglass figure approaching, my thoughts drifted off to the times we had spent together worshiping each others bodies. She liked for me to fuck her tits and cum on her face on a regular basis, and allowed me to fuck her in any position I could name or describe. We had plenty of opportunity, since her parents were often out of town and her father owned one of the finest porn collections I’ve ever seen. We liked to watch the movies and duplicate the scenes. We had a few that were our favorites that we watched frequently, but occasionally she would send me to pick a new one randomly from his porn closet. As you can imagine, she was a distraction at school. It got to the point were I had to make sure to sit in front of her, where I couldn’t see her, so that I would be able to concentrate on the class instead of imagining new ways to get my cock buried in her willing body.

We were finally completely out about our relationship. My parents weren’t too thrilled about it, mainly since they wanted me to focus on my school work. I think it was just that my father spent a little too much time looking at Mary Jane, so my mother didn’t like to have her around. It was good to not go sneaking around and lying, but unfortunately my parents now monitored my activities a lot more. Rightfully so, they worried if we had too much undisturbed time alone together. We made up some stories, and while they thought I was staying late at school for band rehearsals, I was usually watching Mary Jane’s tits bounce as she rode up and down my cock.

As the year came close to ending, the only thing on any junior or senior’s mind was prom. I luckily had my date all lined up, but I wanted the night to be special. I knew I was practically guaranteed another sexual romp with Mary Jane, but I still wanted the night to be special. I had saved up from my allowance and odd jobs throughout the year and arranged to have a limo drive us to dinner and then the prom. I also got us reservations at a really fancy place where I was sure we wouldn’t run into anyone else. I was proud to walk around with Mary Jane, but I didn’t need all those eyes staring at our every move and word. I had kept the plans for the evening a secret, so I was looking forward to her reaction when the limo pulled up in front of her house with me in the back.

When she answered the door I couldn’t speak. She always looked great, but she had clearly gone to special effort this time. Her hair was done in spiral curls that fell about her face, and the only make-up I could detect on her perfect face was the glossy bright red lipstick. The dress was unbelievable. Mary Jane often had problems finding good clothes because of her petite frame and busty measurements. She had found a dress that made her look like a movie star. It was a sparkling emerald dress with matching heels, and though it seemed to defy gravity, it was strapless. It was simultaneously modest and sultry. The design wasn’t so outrageous, but the fact that it was containing her magnificent bosom without any straps made it a vision of sex appeal.


“Ummm… I’m up here,” she said with a smile. It was her classic ‘stop staring at my tits’ line.

I managed to extract my eyes from her cleavage and headed up her chest, intending to look her in the eyes. She was still smiling, and my eyes caught on her ruby red lips. She was still talking and I suddenly was fixated on the red lips, white teeth, and pink tongue. I knew from experience the pleasure that lived in that mouth, and I started to deliberate taking her inside and getting in a quickie before dinner.

“Hey! Up here!” I saw that sexy mouth say. “This isn’t going very well. Do you need a cold shower??” I finally broke the spell despite lingering thoughts of a circle of red lipstick around the base of my cock..

Her beautiful eyes smiled back at me. “Sorry… I was just a little distracted. You look great! Where did you get that dress? It’s amazing!”

She put on her best Scarlett voice “Why Thank You! This old thang? I found it in my sisters closet and made a few alterations. You like?” She spun around, showing me the rear view.

I laughed and said “a few alterations? That must be an understatement.” Her sister was a B cup, tops. “I love the dress. Are you ready to go?”

“Yes, just let me get my purse and we’ll… is that a limo?”

“Your chariot awaits, my lady.” I had practiced that line for a week. I think I nailed it as she promptly took my arm and we walked down to the car. I helped her in and then climbed in after. I motioned for the driver to proceed and then settled in next to Mary Jane.

She leaned against me, pressing one of her tits into my arm. I always wondered if she knew she was doing it. Either way it turned me on. “You seemed a little distracted back there. Is something wrong? Is something on your mind?”

“No, nothing’s wrong. That dress is just amazing on you. I saw you open the door and my brain kind of froze.” I knew she wouldn’t mind. In fact she usually took it as a complement.

“What’s so distracting about this dress?” she asked. As she did, she leaned forward slightly, exposing even more of her cleavage to me.

“It’s just really sexy.”

“What’s so sexy about it? If you don’t tell me, how will I know what to wear in the future?” She got really close and my face was only inches from a wide expanse of titflesh. “You can tell me, what is so sexy about this dress?”

Even though I knew she wanted to hear it, I still felt nervous exposing my feelings to her. I guess that is all part of the game.

“Umm… It really shows off your body.” I thought that would do it, but she started to pout and pull away. She was always trying to encourage me to be more expressive. Once we got things going, I always managed to open up and say what was on my mind, but in general I was a very reserved, shy person. I knew it meant a lot to her if I could just stop holding back and let it out. “I mean…” I had to convince myself to go for it, “your tits look really hot!” I took her smile and nod as an encouragement to continue. “They really are pushed up and out. I can barely look without imagining them bursting out for me to play with.”

“What else, lover?” she knew there was more. “There was something else that kept you from looking into my eyes.” She pursed her lips and extended the tip of her tongue only slightly.

“It was your lips, Mary Jane. They look so shiny and soft, and they contrast with the white of your teeth and pink of your tongue. It makes me want to get lost in your mouth. Okay… I confess, I was daydreaming of taking you inside and using that hot red mouth properly. I was imagining seeing those ruby red lips stretched around my cock.” It was making me hard to talk like that, and she could tell. She kissed the air in front of me and leaned close to my ear.

“Take it out,” she said with her smoky sexy voice. “Take out your cock.”

I had my rented tux unbuttoned and unzipped in seconds. My hardening cock stiffened in the cool air. Mary Jane brought her head down to my dick. She gave my cock a hot open mouth kiss on the head and then swirled her pink tongue around the rim. I moaned “oh yeah… this is so hot.”

Mary Jane gave one last loud kiss then pulled away. I started to whimper just a little, but then she said “Don’t worry lover. I don’t want to mess up my make-up just yet, but I’m going to make all your dreams come true. I have a few surprises of my own in store for you. Just try to keep yourself contained until after the prom and then the real fun begins!” She whispered while casually stroking my cock.

I wanted her to keep going, but I didn’t want to walk into the restaurant with a bulge in my pants, so I gently pushed her away and said “Unless you want me to explode before the party even starts, you’re going to have to go a little easier on my poor cock. He wants you enough as it is. I’m hardly going to be able to look at you without thinking of sex. Then again, that’s how it is everyday. I suppose I can do it for a few hours.” Then I started looking out the window and noticed we were close. “We should be eating dinner soon. Are you hungry?”

She looked me directly in the eyes and said seriously “I’m hungry for your cock. Do you think that’s on the menu?” She saw the shocked expression on my face and started laughing. “Sorry! Sorry, I know what kind of effect that has on you. I’ll try to keep the animal inside. Yes… I am hungry…”

“Good,” I replied, blushing slightly, “We’re here. Let’s eat.”

We had a fabulous dinner in a really fancy place. It was almost embarrassing how extravagant everything was. As expected, we didn’t run into anyone else we knew. As it was, Mary Jane was turning enough heads and causing enough controversies. I saw at least a dozen couples where the man was so distracted that the woman had to snap him out of it physically. There were even two couples who ended up storming out. On their way out, the women invariably glared at us and the men were always trying to get one more look at Mary Jane. All the excitement made me feel special for being close to her, but she always seemed to ignore it. I could never tell if it annoyed her or excited her to have that affect on people.

While we looked at the menus Mary Jane whispered to me, “Are you sure you can afford this? Have you seen the menu?”

“Don’t worry. Get whatever you want, I’ve been saving up for tonight.” In truth I couldn’t afford it. I was going to blow a couple months of savings on this one evening. It was all worth it though, if there was some more ‘blowing’ going on before the evening ended.

“You’re so good to me,” Mary Jane said. “I just hope I get a chance to be good to you, too.” She winked at me.

I don’t really remember what we talked about at dinner. I just kept wondering what sort of surprises she was planning. We hadn’t discussed any plans or fantasies together, and she hadn’t mentioned anything earlier about this being a big night. By the time dinner ended and we were walking out to the car, I was burning with curiosity. As we walked I slid my arm down her back until my hand grabbed her ass. She jumped a little but then settled back down.

“So, what kind of excitement do you have planned for us?” I squeezed her ass a little to encourage her to tell me.

“Now now, you know a secret is only fun as long as it is a secret. You’ll find out in good time.” She swatted my hand away and reached to hold it in her own hand.

“Can I have a hint?”

“Well… I was thinking that we could try an experiment. So it is going to be something new. I didn’t invent anything, it’s just new to me.”

“Is it new to me?”

She looked into my eyes. “Honey, everything is new to you.”

We got into the limo and rode to the prom. On the way I tried not to stare at her. I was really turned on by all the anticipation and almost wanted to skip the prom and move straight into the after-prom festivities. She kept posing for me and giggling at my condition. Finally she slid over close to me and snuggled against my arm.

“I’ve really been thinking a lot about our relationship,” she started. “You really are something special, and I think that we have a really great thing going here.”

“Yeah?” I wasn’t sure where this had come from.

“I just want to be sure that you feel the same way, too. I don’t want to get too involved only to find out I was being a fool.”

I was not at all sure what she was thinking. She obviously had something on her mind. Every now and then she got a little insecure and needed to hear about my feelings. I was always completely sincere with her, and I had developed what I thought were true feelings for her. Looking back, I realize that those feelings in the beginning were helped a lot be the frequent and intense opportunities to get into her pants. At the time, however, I thought it was the real deal, so I told her.

“I’m completely there with you, Mary Jane. I wasn’t sure what was going on or how to transition from you being my ultimate crush to you being my girlfriend, but I think I’ve figured it out. I think about you almost all the time, and I only want to protect you and make you smile. You aren’t a fool. You’re my angel.”

“Really, I’m your angel?” she looked at me with perfect brown doe-eyes.

“Yeah… my angel. You represent perfect beauty and love, and you watch over me when I sleep. How else do you explain how you end up in my dreams. At the same time, it’s my little secret that sometimes you’re no angel at all. And as long as you share that side with me only, you’ll be my perfect angel.”

She rested against my arm and said “You’re amazing. How did I get so lucky to end up here with you?”

“I’m the lucky one, Mary Jane.”

“You just go on believing that, but I thank God everyday that you stand next to me and give me your love. I know I don’t deserve it, so I’ll do whatever it takes to keep you in my life.” She was really holding on to me now. Sometimes she got really scared about being alone. I think it was left over from rocky times in her parents’ marriage when she was five. She claimed her mother and father took turns staying away for weeks at a time, leaving in the morning and not coming back until the fight cooled off. Who knows what actually happened, but filtered through a five-year-olds need for security and permanence, it left her with strong abandonment issues.

“I’m not going anywhere, Mary Jane. I’m all yours.”

She smiled and said. “You always know what to say. And it always works.” She looked out the window. “We’re here! Wow, look at how they decorated it!”

We rolled up to the prom, got out, and made our way inside.

We spent the prom dancing with each other and talking with friends. Most of the conversations for the evening revolved around who was there with whom, and what everyone was wearing. Some girls had really gone all out and were wearing really fancy, though slutty, dresses. None of them came close, however, to matching Mary Jane’s sheer sexuality. No amount of leg slit or cleavage or skin-tight design could make up the distance. I felt like I was king of the school walking around the prom with this stunning beauty on my arm. Our dancing was getting really hot. On slow numbers I held her close to me. I could feel her breasts pushing into me, and I’m sure she could feel the hardness of my cock against her stomach. She was almost short enough to feel it against the bottoms of her tits, but not quite. As the evening wore on, we added some kissing and then a little groping to the dance routine. After a couple of hours, I had forgotten that anyone else was even there. I probably would have stripped her out of her clothes right there. Somehow I stayed aware enough not to make that mistake.

Mary Jane was also feeling more aroused. I could feel the heat from her pussy emanating out from between her legs. I asked her “Why are you getting so turned on?” It was a bit facetious, my hard cock had been poking her the entire song.

“Mmmhh… I’m just thinking about later.”

“What about later?”

She pulled me closer and brought my head down so she could whisper in my ear. “Are you ready to hear about my secret plans?”

“Yes. If you’re ready to tell me.” I had been imagining what it could be. The only thing I could come up with was that she was going to invite some other people into our hotel room and we would have an orgy. We had seen some movies with group sex in them, but we had never discussed it as an option. I was willing, I just wondered whether Mary Jane would recruit another boy or another girl, and who? Then again, maybe I was just completely wrong. “You said it was something new and exciting. I’ve been turned on all night wondering about it. What is it?”

As Mary Jane whispered, I could actually feel her nipples harden through all our combined layers. I could feel her muscles tense and relax as if she was having a mini-climax right there on the dance floor. “Tonight, I’m going to let you fuck me…” she paused, as if contemplating for the last time, “in the ass.”

If I thought my cock was hard before, I was wrong. NOW it was hard. I could feel myself growing in my pants. I felt bigger than ever. My cock was throbbing just at the thought. “In your ass??” I whispered back. “Wow. I don’t know what to say.”

“That’s okay. I can feel how much that excites you. I’ve been thinking about this for a while. I saw it on one of my father’s movies and wondered what it would be like. I wanted to save it for a special time and a special person. Now that I know you feel as strongly for me as you do, there couldn’t possibly be a better opportunity.” Mary Jane let me stand up straight and held her body tightly against mine. We finished the dance and we made a quick exit. We were both ready and excited about the prospect of getting my cock into Mary Jane’s back door.

We piled into the limo. Mary Jane told the driver where to go. Here was where her planning picked up and mine ended. She had reserved us a room at a hotel where we would stay until making the rounds of the after-prom breakfasts. She had gone to the hotel earlier in the day to drop off all the ‘supplies’ we were going to need.

“I have to admit I’ve been sort of practicing to get ready for this,” she said shyly.

“Practicing?”

“Well, I read in one of the magazines that it is easy to get hurt if you aren’t ready, so I’ve been ummm… preparing my body to take your dick inside me. I probably wouldn’t have had to bother but you’re pretty big and I was worried it would hurt. I got some lubricant they suggested and some condoms. I know we don’t have to worry about getting pregnant, but the magazine said it is better for everyone all around if we use a condom.”

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