My Friend Sarah
Introduction:
Sarah’s first anal experience is painful.
Sarah was a pretty 18 year old girl. She had been a dancer most of her life growing up and along with that came a trim, thin body. She was also tall, around 5’10” to my 6’3″, and had a wonderful set of breasts. It was no surprise that, in addition to enjoying spending time with her due to her funny personality and our friendship, I was also quite attracted to her.
Luckily, she was equally attracted to me. For some reason that I still can’t pinpoint we never decided to be a couple, probably because we were both enjoying being single college students, but we did become “friends with benefits” and would screw around every-so-often. My favorite was receiving head from Sarah. She was, flat out, amazing at it. Still the best I have ever had! What made her so good at giving oral sex, you may be asking? I believe it was because Sarah truly enjoyed it. Most girls only give their guy a blowjob out of obligation. They feel they owe them a BJ once-in-awhile just to make sure the guy keeps going down on them. Not Sarah! She told me one time that she loved the feeling of the cock in her mouth and LOVED knowing how happy she was making the guy. It was a turn on for her to get the guy off with her mouth!
One Friday night we had gone out to a campus bar with a group of our friends. I had gotten a pretty decent buzz, but there just didn’t seem to be a great crowd out that night. I wasn’t having a ton of fun and instead of continuing to spend money on crappy beer, I just decided to call it a night and head home around midnight. I said good bye to my roommates and started to head for the exit when Sarah saw me.
She caught me just before I got to the door. “Hey, where are you going?”
“Eh, I’m heading home. Just not having a great time tonight, ya know?” I replied.
Sarah looked a little disappointed at my answer.
“Well, would you mind if I joined you then?”
“Are you sure?” I asked. “I wouldn’t want you to leave if you are having a good time.”
“Well,” she began, “I was kinda hoping to come home with you tonight, if you know what I mean.”
I just smiled and we headed out together on the short walk back my house. When we walked in the house we headed straight for my bedroom and locked the door. We were immediately all over each other. We began a passionate kiss, tongues interlocking, my hands reaching up and fondling her through her shirt, which came off in no time. We definitely knew why we were there.
We were now lying in my bed, both completely naked, making out. My hands were moving everywhere on Sarah’s body, but especially playing with her breasts. Sarah was straddling my body as I lay on my back. She had positioned herself on me where her wet pussy was sliding slowly against my shaft as we made out. And then she began to move down my body. I knew what was coming and I couldn’t wait!
Sarah was now at the foot of my bed, body bent over and she lowered her mouth to my cock. It was already wet with her pussy juices so it slid in easily. I was in heaven! Fuck she gave great head!
Her right hand wrapped around the bottom of my shaft and her mouth began to slurp up and down my pole. I reached down and pushed her hair over to one side of her face, I love to watch girls suck me off. She continued to move her head up and down in a steady motion. I felt her tongue moving all over the underside of my shaft.
Occasionally Sarah would flatten her hand on my stomach and deep throat my entire 6 inches. As my head hit the back of her throat she would hold there for a second and move her throat muscles. The more she got into the more saliva was building up and I could hear the slurping noises being made during this truly expert blow job. It was truly incredible!
But then again, so were her breasts… “Sarah,” I began to ask, “Can we try something different?”
She pulled her lips off my dick with a popping noise. She looked up at me with a smile. “What is that?”
“You have incredible tits, do you mind if I fuck them?”
She didn’t even answer, she just moved off the bed and knelt on the floor and motioned for me to sit up on the edge of the bed. My legs were parted on the two sides of her and she moved closer to my body. She grabbed both breasts and moved them over my shaft. Sarah began moving her tits up and down my cock, slick with her saliva. She watched it slide along her body and occasionally looked up into my eyes, which were half closed enjoying the pleasure, half open watching the act being performed on me.
Sarah just kept moving them up and down along me, practically bobbing her entire body to get me to slide more between her tits. After a few minutes Sarah had me at my limit.
“Sarah, fuck, I’m gonna cum,” I stated almost desperately.
She moved her breasts away from my cock and practically dove down to take it in her mouth. She pushed all the way down one time and as she moved back up on my dick I exploded in her mouth, pumping out two or three days of built up cum.
Once I was done spurting, Sarah sat back on her heels and opened her mouth. She hadn’t swallowed yet. She showed me my load and began to play with it in her mouth, swirling it around with her tongue. At last she closed her mouth and swallowed it in one big gulp, opening her mouth to show me it was gone!
I was spent! — at least for a few minutes, anyway. “Get up here,” I commanded Sarah, and reached out to help her to her feet. As she got up on the bed I rolled her onto her back. She knew it was her turn to be on the receiving end of things and simply laid back and spread her legs slightly.
I moved my body between her legs and up her lithe body and lowered my mouth to her left breast. I extended my tongue and lightly licked circles around her breast. I started first with small circles around her nipples, then making larger ones the farther away I moved from the center before slowly condensing the circles back to her now hard nipple.
I slid a hand down to Sarah’s pussy and began rubbing her already wet and swollen clit. While fingering her, my mouth continued to play with her nipples. I opened wide and sucked in as much of her breast as possible and began swirling my tongue around, then sucking hard. I alternated sucks with nibbles of her nipples.
Finally, I moved down Sarah’s body, licking her stomach the entire way before my head was between her spread legs. Sarah’s pussy was practically running like a faucet and I moved my tongue in to lick up her sweetness. She shuddered as my tongue ran across her clit and then started lapping at her juices.
Just like for Sarah, getting a girl off orally was a turn on for me. The more Sarah moaned her “ooohs” and “aaahs” the more I licked. I was infatuated with the taste of her and couldn’t get enough! As she moved closer to her orgasm I made sure to maintain a steady rhythm on her lips and clit. I saw her lower back begin to arch and looked up her body to see her head roll backward as she moaned, “I’m cuuuuuummmmmiiiiinnnnggggg!”
As her orgasm began to subside I kept licking at her clit. The sensation became too much for her and her body began jerking, almost like she was being tickled. Sarah reached her hands down to my head and started to lift it up, nonverbally saying that she had enough of the oral assault. I moved back up her body and kissed her again, making sure she could taste herself on my lips and tongue.
As we kissed, Sarah reached her hand between my legs and began pulling on my member. I was already half hard from the excitement of going down on her. I quickly hardened in her hand.
“Fuck me now!” Sarah demanded as she looked me dead in the eyes. I reached over to my drawer and pulled out a condom, opened it and rolled it on. I had bought the type of condom that has a numbing agent on it to help last even longer than normal.
Sarah remained on her back, legs spread wide open as I positioned myself above her body. In a sort of push up position I placed my cock at the entrance to Sarah’s pussy. She reached out for my cock and guided it in.
“Oh yeeeessssss,” escaped Sarah’s mouth. I had just entered her sopping pussy. With the “extended pleasure” condom on I couldn’t feel nearly as much please as she was, but I loved the thought of fucking her for a very long time. I didn’t waste any time and just started pounding her.
I put each of Sarah’s long, slender legs up on my shoulders and slammed my cock all the way into her. Her eyes went wild with enjoyment as I pulled back out and quickly found my target again. Time after time I repeated the process — pulling all the way out until just the tip of my cock was left inside of Sarah and then in one stroke pushing back in until my abdomen was touching hers. Just below where her knees were positioned, I could see Sarah’s large breasts swaying up and down on her chest — I loved that sight!
She knew my roommates weren’t home and likely wouldn’t return from the bar for some time now, so she obviously decided that she was going to enjoy the empty house — something that was not often afforded to us college students.
“Fuck me, fuck me, fuck me,” Sarah began yelling to her hearts content. “Oh my God! That feels so good, fuck me harder!”
I oblige her request and fuck Sarah as hard as I possibly can. I am amazed that I am able to keep going as long and fast as I have been. Normally if I continued this assault for this long I would be pumping a steady stream of cum by now, but not tonight. As I’m having that thought, I suddenly realize that Sarah is on the verge of her second orgasm.
“Oh, oh, oh, oh, fuuuuuuuuccccccccckkkkkkk! I’m cumming. I’m cumming. Keep fucking me!”
As Sarah finishes her orgasm I slow my thrusts. I’ve been on top for awhile now supporting my weight and my arms and hips are getting tired.
I pull out of her and Sarah has a disappointed look on her puzzled face. “I want you on top now,” I explain. Sarah quickly gets up on her knees giving me room to lie down and then straddles me.
Quickly, my cock is again embedded inside of Sarah. Just as I had not held back in fucking Sarah when I was on top, she was not going to go slowly, either. Sarah leaned forward, putting her palms on my chest for support and started bouncing on my cock. Up and down she went as she shifted her hips.
I was in heaven getting fucked and watching Sarah’s tits move with her body. She had her eyes closed and just enjoyed the feeling of my cock penetrating her. I reached out and grabbed her small butt and then pulled myself up so that I was sitting up with Sarah’s breasts right in front of my face. I dove into them like they were pillows and began motorboating her breasts, moving my face side-to-side.
I took one of her nipples in my mouth and sucked greedily, as if she could feed me from them. I kept sucking her breast, occasionally swirling my tongue around her nipple or biting it gently. Meanwhile, I grabbed her both ass cheeks as hard as I could and kneaded them as if they were bread dough as she continued sliding up and down my rock hard dick.
Sarah’s head was thrown back as she just enjoyed the feeling of my cock inside of her. Still yelling at the top of her lungs as I fucked her, I heard her say, “Keep going. I’m almost there again. Keep sucking my tit like that. I’m … almost … there …”
Sarah came again. And I wasn’t even close yet. She kept bouncing on me as she orgasmed and I just kept going strong. I love these condoms!
As Sarah’s orgasm subsided and she slowed her pace bouncing on my member, she said some magical words.
“Fuck this feels so good. I will do anything you want right now!”
“Anything?” I asked.
“ANYTHING,” she responded deliberately. Saying these words, she knew what I would request. For as long as we had been hooking up I had been asking for anal. Sarah had always said ‘no’, but tonight was going to be a ‘yes!’
“OK, I want anal.”
There were no questions. Sarah slid herself off of my cock and allowed me to get up. When I moved, she moved to where I had been on the bed, but got on her hands and knees.
I got to my hands and knees behind her and stuck my tongue out to her pussy, giving it a few licks. I then started my tongue at her clit and took one long lick all the way up until my tongue was past her puckered asshole. She jumped a little, surprised that my tongue would go there. I then settled it on her hole and began tossing Sarah’s salad. I got the feeling that she was a little uncomfortable with this at first, but after a few licks she gave in and began moaning as I licked her musky ass.
After a minute or two I slid a finger into her pussy to get it wet and then, moving my tongue to concentrate on the top of Sarah’s asshole, I removed the finger from her pussy and pushed it into her ass. I heard her inhale sharply as I penetrated her ass and her ring clinched around my finger.
“You need to relax, Sarah, or this is going to hurt more than it needs to.”
I kept working my finger in and eventually she let it in. After a minute of one finger, a second one entered her. Gone was the yelling from Sarah earlier, now she was silent as she concentrated on the feeling of fingers in her ass for the first time. I twisted my fingers around for a few minutes, then pulled them out. It was time for her to feel a cock in her tightest of holes.
I got up on my knees and removed the condom. I moved closer to Sarah’s waiting body and placed my shaft against her. I rubbed it up and down her for a moment and then pushed it into her still gushing pussy to lube it up a little.
“Oh fuck that feels so good,” Sarah yelled again. “How about you just keep doing that? You’ve always wanted to cum inside of me without a condom!” She was obviously nervous about the anal fucking that she was about to experience and was trying to get me to ask for anything else instead.
“Now, now,” I said. “You said I could do ANYTHING to you, and I want that virgin ass of yours.”
I pulled out of Sarah’s pussy. With one hand I grabbed her butt and pulled a cheek to the side. With the other hand I grabbed my cock and lined it up to her ass. I pushed forward slowly but forcefully. She was still very tight, but the head of my cock pushed through and entered Sarah’s ass.
“Oh fuck!” she screamed, for the first time all night it was not out of pleasure. “Oh my God that fucking hurts! Take it out. Take it out please!”
“Just relax,” I encouraged her. “Just wait a minute and you will get used to it.”
“No, please take it out. It hurts so much.”
“Sarah, I’m not taking it out. You are going to take my cock in your ass, just relax and get used to it.”
She tried to squirm, but I now had both hands on her hips and she wasn’t strong enough to move away from my grip. I leaned forward until my chest was almost laying on her back and I wrapped my arm around her waist so she couldn’t move.
As I held on to her, I began pushing forward again. Slowly I entered her ass little-by-little, pausing about every inch or so to give her time to adjust. Each time I moved forward she begged me to stop.
“I promise this won’t hurt in a few minutes,” and I kept pushing forward until I was completely buried inside her ass. I pulled back slowly and then pushed forward. Her ass was definitely loosening up so I picked up my pace a little, but she kept complaining about the pain. And I know this is horrible, but I was starting to get even more turned on by her complaints.
“Yeah, fucking tell me it hurts, baby. Tell me how much my cock is hurting your poor, tight little ass.”
“Oh my God, nothing has ever hurt so badly in my life, please stop!” she pleaded with me. But there was no way I was stopping until I came inside of her.
“Yeah, tell me it hurts. Tell me you like the pain! Tell me it hurts so good!” My arm was still around her and my hand was squeezing her tit as my other hand fingered her pussy.
“But I don’t. I don’t like it. Please stop.”
“I said tell me you like the pain!” I ordered.
“I love it. I love the pain of your cock stretching my ass! I hurts so good. Please keep fucking my ass.”
I was fucking her pretty good now, increasing my pace with each thrust. “Tell me you want it harder.”
“Harder, harder,” she yelled, “fuck my ass harder! God it hurts so much and I fucking love how much it hurts! Fuck me harder!”
I knew the words weren’t genuine. She was definitely not enjoying her first ass fucking. But she was doing a great job of making me believe she liked it. She probably sensed how turned on I was and figured the more turned on, the faster I would cum and this would all be over.
And she was right. For the first time all night I could feel the cum boiling up inside of me. I straightened up from the position I had been in and grabbed her hips and pounded Sarah’s ass as hard as I could. My balls were slapping against her pussy as I fucked her harder. I could see her tits swaying uncontrollably underneath her.
Finally, I was ready to cum. I pushed inside of her one last time and felt my load explode into her ass. One spurt, then two, finally six spurts and my cock was left just dripping a few last drops inside her ass. I slowly pulled out and pulled her cheeks apart. I could see the load I had deposited in her begin to leak out down her leg.
I let go of her ass. “On your hands and knees on the floor,” I ordered her. I got off the bed and stood up. Without objection, Sarah got on her knees and took my cock into her mouth and sucked me clean. She could taste her own ass and a little bit of my cum as she sucked my shrinking cock up and down. Finally, she stopped and stood up. I looked down again at her wonderful breasts and I could see cum sliding down her legs.
“Did you enjoy that?” she asked. “Because that’s the only time you are ever getting it from me.”
“I sure did,” I replied with a smile. “And that is definitely NOT the only time I will be fucking your ass. You had better learn to enjoy it!”
Without disputing my statement she simply replied, “well, you had better make that up to me now!”
“I’ll do anything you want,” I smirked back.
