HS Sweetheart Ch. 04


“Okay. I’m still amazed at this. Are you really going to let me in your ass?”

“I sure am. I want that long hard cock to fill up my ass and fuck me like no one has ever fucked me before. I want to give myself to you completely. I want you to know that I am 100% without a doubt all yours and that I have given every piece of me over to you.” Her breathing had deepened and I could tell she was getting turned on.

“Knowing you, I’m surprised you’d want me to use a condom.”

“Why? I’ve always been a big supporter of safe sex. I never let you anywhere close to my pussy without putting a condom on.”

“Yeah I know, but how are you going to feel me pulse inside of you and deposit a load of cum deep inside your ass? I know how much you love cum. Would you rather I pull out like we do sometimes and cum on your face?” I was surprised we hadn’t torn each other’s clothes off in the limo. The sexual intensity was unbelievable.

She smiled and said “I already thought of that. I have a plan to get that yummy cum to fill up my ass. I’ve heard great things about how that feels.”

We got to the hotel, paid the driver, and went up to the room. In the elevator, Mary Jane grabbed my cock and slowly pumped up and down its length. “Wow baby. You feel extra big tonight.”

“I feel huge! Like we discussed I haven’t been with you or jacked off for nearly two weeks. Combine that from spending the evening with you and THAT body in THAT dress and I am so ready to explode I’m having trouble holding back.”

Mary Jane kissed me on the lips as the elevator doors opened. I middle aged man waiting to get on stared just a little to long at Mary Jane’s voluminous chest and was rewarded with a smack on the head from what I suppose was his wife.

We walked into the room. I followed Mary Jane in and before she could turn around, I put my arms around her and pulled her back against me. I could feel her press back into my hard cock, moving her ass around as my hands dug into her tits.

“Do you like my cock? Do you like feeling it against your ass?”


I leaned down to kiss her neck and she moaned. She leaned her head to the side to give me easier access, but she was also giving me a better view down her dress.

“I have a great view of your tits. Do you like that I can see your tits?”

“Yes. Oh baby”

“Do you want me to touch them? Do you want me to grope at your tits and press my cock against your back?” I had been practicing in my mind this scene. I was planning on being more aggressive tonight, but I hadn’t counted on anal sex coming into the picture.

“Mmmm Yes I want you to squeeze my boobs and use them for your pleasure. You can kiss them, lick them, bite them, fuck them. Ooohh… I know you want to fuck my tits.”

“I do want to fuck your tits. I want to lick them to get them slick and then slide my cock in between them. I want to fuck your tits until I have to cum. And then I’m going to give you all of my cum, just like you like it.”

“Yeah? How is that?” She asked, panting in my arms. Her ass was really writhing on my cock.

“On your face. I’m going to step back and let my cum fly all over your face. Isn’t that what you like?”

“Yes! Yes! I want it! I want to feel all of your cock juice spraying on my face. I want it to drip between my tits. I want to have it splattered all around my red lips so I can get it with my tongue. Are you going to cum on my face? You can right now if you want. I’ll just kneel in front of you and let you do it. You don’t even have to touch me first.” She was so worked up, it was time to drop the bomb. It was her own bomb, but I still liked the idea of her being too turned on to say no to me.

“I’d like that.” I undid her bra and then grabbed one of her tits with one hand. With the other I reached around and plunged into her underwear where I easily found her hot and soaking pussy. This also had the effect of pulling her back further to press harder against my cock. “But first, I’m going to fuck you in the ass. I’m going to bend you over and fill up your ass with the long hard cock you feel pressing against you.”


“I’m going to fill you up until you orgasm with my cock buried in your ass and then I’m going to fuck you. I’m going to fuck your hot tight ass and fill it up with my sperm.” My fingers strumming on her clit and nipple were making her dance against me. I could tell she was getting close. I knew she liked to start an evening off with an orgasm, so I didn’t let up and felt her build up to the big release.

“Do you want me to do that?” I asked her.

“Yes! Yes! Please do it to me?”

“Do what to you?”

“I want your cock in my ass! I want to feel it and fuck it. I’m ready for you to just fill up my ass with your pole. I’ll do anything for you. Fuck my ass!” With that I pushed Mary Jane so she fell on the bed. I turned her over and knelt in front of her steamy pussy. I immediately dove down with my tongue on her clit and started fingering her pussy hole. She was moaning about my cock and her mouth and her ass or something when I pulled my finger out of her pussy and started to press it into her ass. I figured that if she was ready for my cock she must also be ready for something smaller. The lubrication from her pussy helped and my finger slid in a couple inches.

Mary Jane started moaning even louder and I’m sure she was pressing back against my finger. I stared pulling that finger out and then pressing it back it. As I did usually with her pussy, I added another finger. Fingering her asshole was amazing. It was hotter in there than in her pussy, much tighter, and so much more naughty it made the event that much sexier. I started really letting my fingers pound in and out of her ass and kept up my oral assault on her clit. Within minutes I had her writing around in one of the most intense orgasms I had ever seen.

“Yes baby Yes! Give it to me! Lick me! Fuck me! Oh my ass! I’m cumming! I’m cumming! I’m cummmmmmmmm ohhhh myyyy Goooood cummmmming!!!!” The last was really that long. Her ass clamped down on my fingers until I couldn’t move them. By the time she relaxed enough for me to pull away, her breathing had nearly returned to normal.

She looked at me with starry eyes. “That was amazing. I thought I was going to make the first move and then you just attacked me. I’m so proud of you! Whew! Any more surprises?”

I stood up and started undressing. “The only surprise left is how good you’re going to feel when it’s my cock instead of a couple of little fingers.” While I was taking off my clothes, she pulled a tube of lubricant and some condoms out of a bag she had stashed next to the bed. I gently stroked my cock to keep it hard while she opened up a condom.

“C’mere, we need to get that guy dressed for the party.” She beckoned for me to approach and then grabbed my cock. “But first, I believe you requested a ruby red blowjob, right?” She reached into her purse by the bed and pulled out the tube of lipstick. She applied a thick fresh coat and asked “How does it look?”


“Don’t you mean ‘Mouth-fucking-tastic!’?” she made a kiss with her lips and I walked my cock right up to her face. She opened her lips slightly, stuck her tongue out and lightly flicked at the head of my pole. I used her tongue as a guide and thrust straight into her mouth. She let me slide in until I felt the back of her throat before closing her lips and massaging the underside of my cock with her tongue. I could feel her pressing her lips tighter than usual. Then she released and pushed me away. She was careful not to let my cock head drag against her lips on the way out. “Mmmm… that is a MUCH better way to get rid of the excess lipstick than using a tissue. How does it look?” She gestured to my rigid cock.

I looked down and saw a glistening pole with a ring of bright red lipstick an inch or two from the base of my cock. “It’s perfect, baby. Now get those lips back around my cock and see if you can’t get that red ring all the way down.” She responded brilliantly to my challenge. She never had trouble getting all 8 inches down her throat, but she usually needed a little inspiriation. “Yeah baby, take my cock. You like it in your throat. My dick is sliding all the way in. You look soooo sexy with my cock filling your mouth like that.”

“Mmmmph mmmph ammmamph” She mumbled back.

“What? I can’t understand you. You have a long hard cock in your mouth.”

She pulled off and said, “Are you going to fuck my mouth all night? What does a girl have to do to get some ass fucking around here?” With that she dropped my cock into her cleavage and gave me a few pumps with her tits before rolling the condom on. “Here, put some of the lube on that, and then put it on me.” She rolled over on the bed onto her hands and knees and then stuck her ass back at me.

I was surprised at how, well, lube-y the lubricant was. I slid some onto my condom-covered cock and was amazed at how slick it was. I climbed on to the bed and made my way behind Mary Jane. I put some more lubricant on my fingers and started to rub it into the outside of her pink puckered asshole. She moaned “Mmmm… that feels good. Put it inside, put it inside.”

With a grin, I positioned my almost painfully hard erection in front of her steamy pussy. I wanted to give her a real thrill, so I simultaneously slid my lubricated fingers into her asshole and my raging hard-on into her cunt. As her heat enveloped me I sighed and moaned. She let out a gasp and a “Ooh!” as I filled both her holes. I left my cock in place and greased up her ass with my fingers. I added another finger just to make sure she would be stretched enough for my cock. “Does that feel good, Mary Jane?” I asked.

“Yeah… it feels nice. Kinda weird, but really nice. It’s especially nice to have my cunt filled up while you do that.”

I started stroking with my cock. I was really taking my time with long easy strokes. I pulled almost all the way out and then pushed slowly until my balls were resting against her clit. She was moaning softly and pushing back on my pole. I pushed my fingers deeper into her ass until I was sliding in and out without any difficulty. I knew it was going to be hard to get in with my cock, but I wanted her as ready as possible for my anal invasion. “Are you ready baby?” I asked gently.

She turned her head to look at me with her deep brown eyes. “I’m ready lover.”

I gave her a few more thrusts deep into her cunt and then put the head of my cock at the entrance to her ass. Her pink, starry, asshole awaited my penetration. I wasn’t really sure what to expect, but I was smart enough not to expect to slide in. I started to gently push my cock into her asshole. I didn’t get anywhere at first, but Mary Jane obviously loved it. Then, slowly, her ass opened to let the head of my cock in. Once her hole had expanded around the head, it was much easier to slide the rest in. I stroked in and out, slowly, getting a little more of my pole in her ass each time. Now Mary Jane was moaning even louder. By the time I was fully embedded, I could feel her fingers on my balls as she stroked her own clit. I sank all the way, fully up to the hilt in her back door. I waited there while she got used to the feeling. “How is that?”

“It’s amazing. You fill me up. I’ve never felt this full before!”

“I can’t believe you took me all the way in your ass! It is so much tighter than your little cunt, I’m not sure I’m going to be able to move.” I was really worried we would never get out of this, her ass was so tight.

“You better be able to move! How else are you going to fuck my ass?!” With that she started rolling her hips slowly beneath me. I matched her motion by pulling back and then pushing back into her ass. Eventually, her asshole loosened its grip on me and I was sliding in and out like I was fucking her pussy. Only when I looked down at her body, I saw the ultimately erotic sight of my big fat cock stretching her asshole.

The pleasure was intense. Her ass squeezed me and I started to really ram my cock into her. It didn’t sound like she objected too much. She kept up urging me to fuck her harder and to give her all my cock. I didn’t want to let her down. The only downside is the whole experience was driving me faster and closer to orgasm than usual.

“Baby I think I’m getting close.”

“Mmmm yes… I want you to fill my butt with cum. Let me feel your cock cream pour into my ass!”

It all sounded well and good to me, but I was wearing a condom. She would be able to feel the throbbing as my cock expanded and then twitched its way through what I expected would be a powerful orgasm, but wouldn’t actually get any cum inside her. She shouted out “Take it off! Cum in my ass!”

Could you say no to that?

I kept stroking and she started shuddering and I knew her climax was upon her. At the last moment, I pulled out, and tore off the rubber. As my cock started to throb, I placed just the tip of the head at the entrance to her back door. It was still gaping slightly from my assault, but was already starting to pull itself closed. The sexy sight pushed me over, and I sent four spurts of semen into the darkness of her bowels. Her shouts of encouragement excited me a little too much and I lost my aim. Several bursts of cum arched their way over her ass and splattered across the back of her head and shoulders. “Don’t waste it! Cum in my ass!” she looked back at me almost glaring. The last of the errant spurts was on its way, and caught her on the nose and lips. That put a smile on her face, but she still wanted it inside her. This time I lodged the head inside her shrinking asshole and stroked out the rest of my orgasm. By the time my cock was done shooting, I was exhausted. We lay down together on the bed, cuddling.

“That was wonderful Mary Jane. How was it for you?”

“I think I found a new favorite thing. I can’t believe how awesome that was. Awesome and naughty… You just fucked my ass!”

“I wouldn’t want to be naughty. We should try to be good people,” I said, egging her on.

“I like it! Being naughty makes me feel alive. I love the feeling, whether I’m sucking your cock, letting you fuck my tits, riding up and down your pole, or getting fucked in the ass, that no one knows what we’re doing here and we can be as naughty and nasty as we want.” She was getting both of us turned on again. Her ass was rubbing back against my growing cock. I reached up and fondled her tits, making sure to pinch her erect nipples. I kissed her neck where she liked and she moaned against me.

“Do you want me to do it again?” I asked her. My cock was poking her in the back. I didn’t wait for an answer. I repositioned my cock and slid it into her reddened asshole. It was slick and open from the earlier cum and fucking, which also made it even hotter. We were on our sides, so there wasn’t much leverage, so I turned Mary Jane on her back and got on top of her, missionary style. Only I don’t think the missionaries were encouraging women to take cocks in the back door. The angle made it tighter, and this way I got to watch her boobs bounce around. Mary Jane tried to confine them, but even grabbing them with her hands didn’t help. “Do you like it?” I asked.

“I love it baby. I love it. I love the fact that your dick is buried in my hot ass. I can wrap my legs around you and fuck you in all kinds of new ways. But my pussy is lonely. We can’t do this all the time or my cunt will start to feel empty.”

I realized I had forgetten to put on another condom. “Oh shit! I forgot about a condom.” I started to pull back.

“Don’t stop! It’s okay… we don’t need it. Just don’t stop fucking my tight little ass!” She grabbed onto my arms and pulled me back in. “That’s it. Just keep on pushing that lovely rod into my ass! Do you like watching my tits bounce? Is that a turn on? Does it make you want to fuck them?”

“You know I love fucking your tits.”

“Don’t stop what you’re doing, keep that cock in my ass. But you promised you were going to fuck my tits. My poor titties are feeling neglected.” She was pulling on her nipples and mauling her own jugs.

“But for now I’m fucking your ass… Oh man… I’m already getting close… Your ass is just too tight!” With that I pulled out of her ass and started stroking my cock. I let out a groan and watched as my cum shot out, just as strong as the first time, only this time it sailed to the pillow above her head.

“Too high! Aim lower! Cum on my face baby!” Mary Jane shouted as she cupped her tits together and up to get them in the line of fire. I let out a few more volleys of cum that hit their target, touching down in stripes that ran from her nipples up to her eyebrows. This orgasm felt like it was coming from the depths of my balls, and I shook as I shuffled up her body to let the remaining spurts drop onto her cleavage. When I was done she had a thick pool of cum gathering at the top of her tits. I scooped up a bit and fed it to her.

“Here you go,” I said. “Just because my cock was in your ass doesn’t mean you don’t get to eat my cum.” I fed her the rest with my fingers. She licked my fingers like she was starving for cum. I even scraped it off of her face until all obvious cum was gone. She still had some that had made it into her hair that I couldn’t get to.

Before we left to go to some of the after-prom activities, we jumped into the shower to clean off the evidences of the evening. We messed around in the shower, but Mary Jane admitted her ass was a little sore. I strummed her clit with my fingers until she nearly collapsed in my arms. We headed out the door, ready to face our peers with the secret knowledge that we had crossed into a new level in our relationship together. No longer was Mary Jane the experienced one and me the shy naïve one. We now were on equal footing.

She looked up at me, kissed me and said “You keep impressing me. I can still feel your cock inside me. I’ll walk around that party tonight with you on my mind.”

“And in your ass?” I finished her thought.

“Yeah… just know when I smile at you… that’s what I’m thinking about.”

“I’m going to have to avoid looking at you. If I know what you’re thinking, I might not be able to keep from getting turned on. And we don’t want me walking around a room of horny teenagers with a bulge in my pants, right?”

“No we don’t. You save that cock for me.”

“Only you.”

“Don’t forget, you still owe me a tittyfuck. I still want to feel your rod thrusting into my chest.” She gave me a kiss and took my hand.

We headed off to the party, content with our relationship and excited about the adventures we’d had and the adventures yet to come. Given all we had done, I could only imagine where there was left to go!

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