HS Sweetheart Ch. 01bypainter0987©
HS Sweetheart: 1.First Night Facial
How can you ever forget your first love? I had to wait until I was a senior in high school, but I ended up living a dream of getting together with the girl on whom I had the biggest crush. I was a bit on the dorky side, and not so comfortable with girls, so most of the social types never really returned my interest. There was one girl who seemed interested in what I had to say. We worked together a lot on class projects and study groups. Maybe she was friends with me to help get a better grade, but she was intelligent enough to stand on her own and contributed a great deal to group work. I was 18 and of course horny all the time. This girl was my fantasy. She knew it, but waited for me to tell her before she made a move. When she did, it was the start of a long relationship that lasted well into college before it self-destructed. These stories are true and represent the sexual adventure roller coaster that was Mary Jane, my high school sweetheart.
Mary Jane had huge tits. Honestly, that was the thing that attracted me to her in the first place. I think everyone in the entire school was attracted to her tits. She was one of those wet dream types: short, slim and stacked. When I say stacked, I mean STACKED. She must have been a 38DDD, but with a 24 inch waist she looked like she was about to fall over. She wasn’t naïve about the appeal of her breasts. In fact, she used them to her advantage, flustering the teachers, flirting with classmates, and irritating other girls. They just couldn’t compete. Add to this hot figure the face of an angel and you have to wonder what she would ever see in a nerdy classmate like me.
And yet she saw something. Or at least, she wanted me enough to encourage me to be more outgoing. Once I confessed my desire for her (though it must have been obvious) she responded in kind. . We were talking on the phone late into the night on her eighteenth birthday, and she convinced me to open up and tell her how I felt about her ‘as a birthday present’. Our conversations had often been sexual, but I always thought she just did it to see how uncomfortable I could get. Ever since my own 18th birthday in the fall, she had been teasing me about how I was legal and she wasn’t and that anything we did could be construed as statutory rape. That had been one of the things keeping me in check. I had been for the most part a ‘rules-follower’, so there was no way I was going to come close to breaking the law. She knew that, so used it to ratchet up the tension. As midnight passed and I was confessing to her how much I liked her and enjoyed spending time with her and thought about her all the time… I paused to say “Happy Birthday Mary Jane!”
Her voice dropped into that sultry range that drove me crazy. “You know, now I’m 18. I’m totally legal.”
“Now there’s nothing stopping you from getting in my pants. And in my shirt.” She was teasing me. She let the implication hang there for a bit. “Now that we’re being honest about our feelings, I think it will be easier to move forward in other areas too.” Up to this point I had never had a girlfriend, let alone kissed a girl, so you can imagine what was going on in my teenaged head.
Within a week, the opportunity was there. Mary Jane was the last of eight kids and so her parents were pretty bored of the child-raising thing by the time she came along. They spent a great deal of time out of the country and figured Mary Jane could handle things on her own. They were actually horrible parents. You leave a kid that looks like that alone and who knows what kind of trouble she could get into. Oh wait… that’s the whole point of this story. Thank Goodness for horrible parents that through neglect turn their children into sexual deviants!!
Anyway, that Friday night, we ended up alone in her house after a show. I had told my parents I would be hanging out with some friends who had invited me to come over. Mary Jane was changing into jeans and a t-shirt and I was trying not to stare at her amazing body. My cock was getting harder and harder as she was telling me about who had done what with whom in the cast. I was absolutely in a trance staring at her tits. Suddenly it was quiet.
“What are you doing?” she asked.
“Uhh.. nothing.” I tried to stay cool and hide the erection that was growing in my pants. “I was just staring off into space. Sorry”
“I don’t think so,” she said. “I think you were staring at my tits.”
I tried to downplay it, but the more she accused me the more she grabbed at them and then I noticed her start to smile.
“It’s okay. I want you to stare at my tits. That’s what they are there for. Go ahead.” She started to spin around and make provocative poses. When she leaned over I could see down her shirt and into that magical cleavage. “Do you like them?”
“yes…” I responded meekly.
“What? I can’t hear you.”
“Yes. I like your breasts.”
She started to laugh. Mary Jane came up close to me and repeated what I said. “You like my breasts? I don’t think so. These aren’t breasts.”
I looked up at her with a question. It was really hard not to just stare at her chest right in front of my face. Her nipples were starting to poke through her bra and shirt and that smile was coming back again. Then she started to explain my mistake by referring to other girls in our class.
“Do you really think these are breasts? Come on, give me a little credit. Natalie has breasts, nice ones in fact. So does Christy. Rachel and Michelle do too. Well… I guess you have to give Michelle the benefit of the doubt. Do you really think these are the same as theirs?”
“Good. I’d hate to think you didn’t recognize what was in front of you.” She started to take off her shirt. “What we have here are the best” she was grabbing them and lifting them towards my face “biggest” she started to reach behind her to undo the clasp on her bra “finest” snap.. it started to fall away “largest” her hands were squeezing them as her bra fell away “TITS in the entire school.” My cock was about to rip through my pants. She looked down and noticed. Again the smile. “You can call them tits, hooters, knockers, jugs, or whatever you want.” She stepped closer until my face was about an inch from her cleavage. I had given up on looking at her face and was staring right at that beautiful rack in front of me. “But when you call them breasts I think you are selling them short. “Now… what do you have to say for yourself” With that she dropped her hands and placed them on my shoulder.
It was heaven. Her triple-D’s bounced away from her chest and she gently pulled me towards her cleavage. I had enough time to say “I love your tits” before I was buried in them. She straddled my legs on the bed and pushed me down on my back. She let her tits hang in front of my face and I attacked them with my lips, tongue and hands. She ground into my crotch. I could tell she liked what she felt of my cock straining inside my pants. I wasn’t sure what to do.
“Mmmm… feels like you have something big too.” And she reached down to start taking my pants off. Before I could react, she had undone my zipper, reached in, and started stroking my dick. “This is amazing.”
“Oh.. Mary Jane. What are you doing?” I wasn’t stupid, just inexperienced.
“Don’t you know? Haven’t you done this before? With this cock I’m surprised you haven’t had most of the girls in the class already.”
“Ummm… no I haven’t.”
She must have sensed my hesitation and fright because she immediately knew. “You’re a virgin?”
“Totally.” I was sure she was going to stand up and put her clothes on. Instead she smiled and pumped my cock.
“I always wondered what virgin cock tasted like”
It seemed like slow motion. She pumped my cock a little harder, leaned down, opened her mouth, and took my cock inside. It was amazing. Now, with 10 more years of experience, I can say that it was one of the best blowjobs I ever received, and not just because it was the first. But it was heavenly. Her auburn hair tickled my leg as her hot mouth moved back and forth over my cock. Her tongue was doing some sort of dance along the bottom and every time she pulled back she gave a loud smacking kiss to my cockhead.
“Do you like it?” she said with a grin as she stroked my cock with her hand and brushed it against her cheek.
“I love it! I’ve never..” I trailed off, not wanting to admit just how inexperienced I was.
After a few more bobs and licks she pulled off again “You’ve never what?” I think she expected more compliments.
“I’ve never felt anything like this.” If it hadn’t been for her constant stroking and just how hot her tits looked framing my cock I might have lost my erection from nerves. If anything I was harder than ever seeing my cock resting in her cleavage.
“I love your tits.” I couldn’t believe I was saying it. But she responded. She cradled my cock between her jugs and started rocking back and forth. I was nice and slick from all the sucking, so I slid in and out even as she applied pressure from the side.
“How about this? Do you want to titfuck me?”
“MMM.. Wow. Your tits are amazing. They surround me and .. oh God!!!”
The last part was cut off as she dipped her head down to suck on the end of my cock that was protruding between her tits and had been poking her in the chin. I thrust my hips up to enhance the titfucking and she moaned in pleasure.
“That’s right baby.. you want to fuck my tits, don’t you? Do you want to pump your cock between them while I suck on it? I love the way your hard cock feels between my melons.”
Her dirty talk sent me into overdrive.
“Suck my dick. Yeah.. that’s right. Wow this is the most amazing thing. You are so hot with your mouth around my cock. Keep sucking.. yeah.. yeah.. look at me while you suck me. Show me how much you love my dick in your mouth. Grab your tits too, Mary Jane. Let me see you squeeze those jugs while you go deeper.”
I thought I had said something wrong, since she backed off. But then she said “Deeper? You want deeper?” And she dove back down, only this time she didn’t stop. She didn’t come back up and instead kept pushing down and down until her lips were touching my balls. Her tongue snaked out and played with my balls as her throat caressed my cock. She disengaged and pulled back. With another smile, she went back. Again. And again. And again. Finally I was moaning louder and louder and calling out her name.
“Are you ready?”
“I feel like I’m going to explode!”
“Perfect.. I want you to explode. I want you to let yourself go and just explode for me.” Her hand reached for my cock and started stroking faster and faster. She started staring at my cock and repeating over and over again “Cum for me baby.. cum just for me. I want your cum, I need your cum, give me your cum.” I was climbing higher and higher and then I felt the peak and the tightening in my balls. She felt it too.
“Oh yeah baby.. cum for me. Let me see you explode.”
I wanted to warn her that it was going to be messy. But I was too busy letting my eyes roll back, my toes curl up, and screaming out “I’m cumming!!!”
Then I was awash in the most amazing feeling. My eyes closed instinctively and I felt like I was flying. I also felt like my cock had turned into a cannon as spurt after spurt of cum shot out of my dick. Mary Jane was moaning between my legs. I could feel her tits rubbing against my leg and her hand kept pumping my shaft.
“Oh yes baby” she moaned. “Give me all your cum. Give it to me.” I kept shooting. She kept moaning. “More More More Ohmigod this is a lot of cum”.
I stopped paying attention to the world and just let myself fly.
When I opened my eyes again, I think it was about a minute later. I was still spasming from the orgasm and Mary Jane was still milking my cock for more cum. She gently squeezed from bottom to top and licked up the little amounts that came up. She was moaning to herself and grabbing at her own tits. When she looked up at me with a smile I almost spontaneously came again. She was absolutely covered in my cum!
There were streaks of it from the top of her head to the bottom of her tits. She was licking her fingers and gathering it from her nipples. She was still purring to herself. I must have been staring.
“Do you like what you see? Do you like your cum on my face?”
She started to pout. If you thought a busty teenager with cum on her face was sexy, try keeping your cool when she pouts. Her bottom lip stuck out and little strands of my cum created a little spider web in the newly created space. As she spoke I could see some of the cum still in her mouth. “Does that mean you don’t like it? I guess I did a bad thing and we’ll never do that again.”
“Oh No.. Mary Jane that isn’t it at all. I loved it. You look amazing. I can’t believe it! I want to do it again! In fact.. just looking at you has me wanting to do it again right now. I can’t believe how sexy you look covered in my cum!”
That must have been the answer she wanted to hear. She grabbed for my cock and started stroking and licking it. I could feel her breasts against my legs and her nipples were hard little points. I reached down to feel her tits better as she swallowed my cock again. Her tits filled my hands to overflowing and I found myself grabbng at them as if they were pillows. Her moans around my cock told me she liked it. I pulled her up off of my cock and switched places with her, placing her seated on the bed as I knelt in front of her. I immediately dove for her breasts. I was mauling the left one as my hand explored the right. I soflty kissed her nipple and brought all of that titflesh together and licked both of them together. “MMM.. I love your tits.” I said through a mouthfull of wonderful hard nipple.
She pressed the back of my head, pulling me further into her tits. “Oh.. baby.. I love it. My tits are so sensitive today.” I looked up at her as I flicked her nipple with my tongue. Her head was thrown back and she was moaning.
As I was looking at her, she came out of the moan and looked straight into my eyes. I could see the cum shining still on her face. She saw me looking around her features and directed my face to the depths of her cleavage.
“Ooh Yes.. right there. Make it nice and slick and wet. You’re gonna fuck these babys with that hard cock until you give me another load of cum! Keep licking.. Oh yes! I want your cock between my tits! Stand up baby and give me a proper boob bang.”
How could I turn her down. Her cleavage was glistening as I stood up with a raging hard-on. She leaned forward and brought her tits around my cock. “Now baby.. fuck my tits and cum on my face.!”
And so I did. I started slowly.. easing in and out as she increased the pressure on the sides of her tits. Her moans spurred me on and my rhythm picked up. Her dirty mouth didn’t hurt either. Just watching that beautiful face under a load of cum spouting out phrases like “Use my tits” “Gimme that cum”, “I want more cock!” was a huge turn on. She had streaks of cum all over her face. There was one spurt that ran straight up the middle over her nose and forehead and into her auburn hair. Two more rose over her left cheek and pooled above her eyebrow. Another similar on the right cheek. Three or four didn’t make it all the way to her forehead but left pools of cum around her mouth and cheeks. She had cum in her hair on top and on the sides as she had pointed my cock all around her face like a cum machine gun. This was what I was looking at as I pounded my cock in between her massive boobs.
Suddenly I felt the tingling rising in my balls. Something was grabbing onto my insides and trying to get out. I tried to warn her. “Mary Jane.. oh baby.. your tits.. oh baby.. I’m gonna cum.. I’m gonna fucking cum for you”
“Cum for me! Cum for me!”
I don’t think she realized how close I was. The first shot cut her off in the middle of a “Cum for mmmm!” It splattered against her chin loud enough for me to hear it and started dripping back down onto my cock. The lubrication made the titfucking easier, but she quickly pulled my cock out and pointed it directly at her face.
Another spurt glanced off to the left and draped over her right ear and across her cheek. It actually went all the way to the wall behind her bed! “Yes!” she screamed. “More cum! More cum! I want all the cum inside your cock! CUM ON MY FACE!!!” While she was going crazy over my cum, I shot out another rope, this time aimed right into her mouth. She immediatley swallowed and opened up for more.
I grabbed my cock from her and started jerking it off onto her forehead. I moved forward a little and made her lean her head down so I could deposit the rest of my load on her head. She LOVED it. “Oh yeah.. jack off on my face! Give it to me like you like it. Cum on my face! You want to cum on my forehead? Oh.. it’s dripping down my face.. more more more!!!!” I must have had seven more spurts of cum that I draped across her forehead so it would evenly drip down. I found that I loved the look of cum on a girls face. There was something primitive and sexy and absolutely submissive about her begging me to drop a load on her skin.
“Wow.. amazing again. I think I have to take a break now.” My cock was already getting a little deflated even as I kept stroking it towards her outstreched tongue.
She was gorgeous. Sexy girl, bright smile, huge knockers, and two loads of MY cum on her face. She smiled at me and asked if I liked the view.
“It is a work of art” I replied. “When do we get to do this again?”
She laughed and said “soon I hope. I have lots of ideas for what to do with that cock. It’s a regular fountain. We might have to wait, though. I’m a little tired.”
I looked at the time and realized I needed to get home.
She saw the clock too and agreed. “You should go. If you get grounded how will I teach you how to fuck and eat pussy??” she said with a monster grin that made my dick rise again. “Easy boy.. no more tonight.. I’m worn out too. Now get dressed and go home and get some sleep. I like my cock well-rested and full of cum.”
I leaned down to kiss her. Our tongues mingled in the middle as I grabbed her tits one last time. To return the favor she swallowed my cock as I was standing up. After a few bobs she stopped and said “Just something to remember me by. Good night baby.”
With a grin I pulled on my clothes and got ready to go home.
“Aren’t you going to wash that off” I said.
“Maybe later.. I want the last thing you see of me tonight to include the work of art you created on my face.” She blew me a kiss, walked me to the door, and sent me on my way towards home.
On the drive home I contemplated the evening’s events. This was the first time I had been sexual with a girl in any way, and I had managed to come away with amazing images, fucked the hottest tits in town, and twice cum all over my girlfriend’s face. Not only that, I had a near promise that I would lose my virginity soon. My mind was racing as I got home, snuck in quietly, and climbed into bed. I drifted off to sleep imagining how hot it would be when we had another chance to get together and she followed up on that offer to teach me how to fuck and eat pussy.
I turned out that I had to wait another week, but it was well worth it.