The Desperate School Outfit


This time I teased him more, starting out painfully slow, stroking him, blowing on him, and giving him the lightest of kisses, before I built up to sucking him in earnest. He just lay there, looking gorgeous, both hands behind his head, watching my raven black head of hair bob up and down on his cock using every trick I knew to turn him on.

Eventually, as my jaw started to ache I had to start taking it slow. Katie had once said he had never cum from a blowjob. Damn it!

I slid up his body and rubbed my pussy against his hard cock, back and forth. My pussy was more sore than before, not less. Biting my lip, I eased his cock head into my pussy. It hurt, and I had to keep stopping short and prepare myself to take in more. Once he was all the way in I just sat there, adjusting to the feel of him.

"I am not going to fight my orgasm now." He said, and my jaw dropped. All that work and he had been resisting his climax? WTF! "If you can fuck me, really fuck me little Stephanie, I am not going to last long." He was smiling that cocky smile, and he had never moved his hands from behind his back. For a second I wanted to smack him. Did he know how big he was?

But I was not about to stop before I got him off. I started fucking him, slowly at first, but picking up speed. My legs were killing me so I mostly lifted myself with my arms, digging my claws into his abs. At least my pussy was soaked! And I was really turned on... Soon I started to cum again, in spite of any pain I felt. I threw my head back as I bounced on his monster cock, and as I came his hands came in from out of nowhere and pinched my nipples through my school girl shirt and his cock erupted inside of me. I've never in my life came as hard as I did that day.

I collapsed on his chest, and Ryan stroked my hair and whispered how amazing I was. I was torn between sheer panic that Ryan had cum inside of me and pure bliss over that same fact. He asked if I was on the pill, and I told him honestly that I was not. He said to meet him tomorrow after school and he would take me to get the morning after pill and take me to the free clinic to start on birth control, and that he would show me how to go about getting refills without my parents finding out. I agreed to meet him.

Then he started giving me a lecture. He said he didn't want me to go fuck random guys anymore, that if I kept it up I would end up dying of some disease. He said anytime I felt like I just really needed sex to call him, since I had his number. "I'm selfless like that." he joked. So this wasn't a one time thing? Excited, I kissed him, and he kissed me back.

Then he told me about his rules. First I would need to be on birth control, because he wanted to keep cumming inside of me. Katie never let him do that, even though she was on it, he told me. I was to be his fuck, and his fuck alone, if we continued things. If I dated other men, I could sleep with them, but only if we had gone out at least three times first. If I was dating AND sleeping with someone else, I could turn Ryan down for sex, but otherwise if he wanted to take advantage of me I needed to be available for as long as this affair went on, and he would be ready for me if I was in need, regardless of if I was seeing someone else.

Since he had dated Katie for four years before he even started fucking me, he said it was fair that he play the other man in my life as well. Not that I could imagine ever turning Ryan down for sex, even now. I thought to myself I would likely be calling him more than he called me and told him I would hold him to the deal. "I assume if you pop the question to Katie you reserve the right to start turning me down?"

He laughed. "No, I don't care how serious I get with your sister, I will never turn you out of my bed." Between kisses, he explained again how he was marginally serious about my sister but he didn't think marriage was likely. That said what we had would need to stay strictly sexual or it would need to end. He had no interest in breaking up with Katie for me.

He wanted to make sure I didn't try to break them up, so he said if Katie up and dumps him our affair had to end as well. Had I not believed he would end things with me, I really would have broken them up by now.

After I agreed to all of his terms he pushed my head down towards his cock, and I took it back in my mouth obediently. It wasn't long at all before he was hard again, and pulling my pouting lips off of his cock.

"You are too sore to fuck me again, and I don't cum from head." He waited for me to make another offer. He wasn't as big as he had been the first time he was hard...

"You can fuck me in my ass..." I offered. Katie had always made a big deal about not letting him do that. She had told me that before, but had I not already known the delight that lit his face would have told me much the same. Knowing Ryan liked it was one of the reasons I let men fuck me in the ass at all. I had wanted practice, just in case.

I lay face down on the bed while he pressed his fat cock into my ass. Had I not just been ass fucked by a much smaller cock just the day before, Ryan would have been way too much for even me, but I lay there gripping the sheets as he grew to his full length inside my tight little ass and eventually came again.

He lasted longer than the first time, and I was sure I would have trouble walking for a week. I was crying, but my pussy and my ass were filled with Ryan's cum, a man I had lusted over for four years. That was worth the world to me.

He hopped off of me and got in the shower. When he came back I was right where he left me, with my legs spread, face down in a torn and soaking wet school girl outfit, and he told me to take my turn in the shower. That I didn't need to look like I had been fucked all day when he took me home. I guess the honeymoon was over. I agreed.

After the shower though, I made the excuse of not wanting to get home with wet hair, so we decided to order pizza. I called my dad and told him I was at a different friend's house, which was true. I dressed in the more attractive of the two outfits Ryan had bought me, and we cuddled on the couch watching TV and eating pizza.

After the pizza was finished, I pulled his cock back out and sucked him idly as he watched the rest of the movie. I offered to spend the night, since it was already 10 pm, but he turned me down since I did have to go to school the next day and he had to work, but he assured me we would have plenty of sex once we got back to his place the next day.

That next day we got the pills, then went shopping for real outfits and discount sexy costumes, as it was the day after Halloween. I told him he could dress me up anyway he wanted...

When I graduated that spring, he rewarded me with my own apartment, complete with a new credit card with a post-it that read "for furniture." I tried to tell him it was too much, but he insisted saying that with Katie moving in with him over the summer he needed a place to reliably get me alone. I was kind of miffed at learning about their plans that way, so I bought really expensive furniture. He was amused, and said if I did not agree to go to college I had to pay it all back. He also said it had to be local so that he could still see me whenever he had the chance, and reasserted that I would be paying my rent to him sexually. Of course I agreed.

Today, I sit and type on my brand new Mac that Ryan bought me, while watching my flat screen television that Ryan bought me, and count my blessings. I mean, apartment aside, I never thought I would be going to college at all, nor did I ever imagine being the personal sex slave of my life long crush. And to think all of this is thanks to one crappy Halloween party, a super bitchy sister, and one fantastic Halloween!

Report Story

byEsotericNiceGuy© 7 comments/ 65497 views/ 21 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

3 Pages:123

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartgetalyfe1, ertyhnb and 19 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (7 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (7)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: