tagAnalMy Sex Date with 10 inches

My Sex Date with 10 inches

byjennyX1984©

You're probably wondering who Eric is. No Eric is not hung like a horse, equipped with 10 inches although I am sure he wishes he was but nevertheless, Eric means more to me then any well hung guy ever could, he is my very best friend in the world and I love him. This story is not exactly about him but would not be complete without him.

It is at pushing, prodding and pleading that I am writing about this recent sexual experience that I had and it is also to his credit that this experience even came about. He always thought I was a good writer and really wanted me to write about this experience after I shared it with him and apparently he had this exact web site in mind, which I learned, he frequents quite often.

It is Eric's belief that all men are very visual and that it is mandatory that I describe myself physically in detail when relating my experience so here goes. My name is Jenny, I'm 23 years old, 5 feet 5 inches, 115 lbs. I have blonde hair, blue eyes. I have a lean tone body. I did gymnastics when I was a kid, was a sprinter in high school and currently run twice a week and work out at the gym twice a week. My best physical assets are my tone legs and tight butt. Eric says I have a butt to die for. I wish I had a little more up top but unfortunately all I ended up with was a B cup so if you're a breast man unfortunately I probably won't do it for you.

My build resembles more Kate Hudson then Brittany Spears. I have the same complexion as Kate and unfortunately like her lacking in the chest department. I'm more the girl next door then the lady in red. I don't wear a lot of makeup and usually dress modestly. I work out and run in a loose T-shirt and regular shorts as opposed to a naval showing skimpy top and short shorts. Its not that I am ashamed of my body or that I'm not sexual, I am very sexual, I'm just not interested in attracting that kind of attention.

Eric was always trying to get me to wear provocative cloth in high school. He would tell me I have a great body and if I put on a little more makeup, did my hair up more and wore some sexy clothe I would easily be a major major hottie at school. He bought me sexy outfits for my birthday. He just didn't understand that wasn't what I was interested in. Most of the girls he went out with were all done up in the latest sexy outfits.

I guess like a lot of gals I'd like to be appreciated for more then just my appearance. I believe my best overall assets are my intelligence, my personality, my warmth, and my perceptiveness. I would always tease Eric that I was his best friend because of my brains. He would always tease back, No, I just like you for your ass and legs. Hopefully you are reading this because you like to read something intelligently written and not just look at pics of a bunch of naked women.

I don't feel I can dive into relating this experience without first giving a little more background about myself and specifically Eric who has been such an integral part of who I am today. Eric, I bet you didn't expect me to write about you when I finally agreed to write this!

Eric is wild, adventurous guy and a free spirit. He is charismatic, charming but moody. He is spontaneous and likes to fly by the seat of his pants. He has never had a problem meeting girls and even in middle school he went out with the most popular best looking girls. I on the other hand am a little shy. I am more of a thinker planner then fly by the moment. I am not good at uncertainty and get nervous a lot more often then him. I am open minded and willing to try most things. I love sex and probably masturbate more then most women but I'm not a nymphomaniac by any stretch of the imagination. I've slept with less then 15 guys in my life and have never had group sex although I am open to the idea with the right people.

I've known Eric since I was 10 years old. He lived down the street from me and we just clicked right away. Seems like we became best friends from the moment we met. He was big for his age then and I was tiny for my age. He called my Little Sis and looked after me even though I was actually a month older then him. We went through our turbulent adolescence years together and he was always there to lend an ear or a shoulder to cry on if I needed.

He was the person I called the night I lost my virginity and I was the first person he told when he lost his. He is someone who knows me forward and backwards, with whom I've shared my deepest darkest secrets. Strangely enough we were never really boyfriend and girlfriend although we shared many passionate encounters. At times we are like brother and sister and at other passionate lovers. He is the friend I've always wanted the brother I never had and even my knight in shining armor.

There was a guy I regretfully slept with in high school who went around spreading derogatory rumors about me. I became very distraught and confided that day after school to Eric with tears in my eyes. Eric was enraged seeing me crying. Just at that moment the guy came out of the school with his buddies. Eric ignoring my protests ran up to him jumped on him and attacked him. Despite being out sized and out muscled he gave better then he got. He got a black eye and a week suspension for defending my honor but he forever won my gratitude!

In our senior yearbook where seniors can share their best memories for all to read, mine read "Being with my homie, best friend and big brother Eric thru the good times and bad. I couldn't imagine growing up without you. Thanks you for always being there for me! You will forever and always be my best friend. I love you."

His read "Spending my 18th bday with my best friend Jenny. Thank you for the most incredible night of my life! Love you little sisl!" I will have to elaborate more on what exactly happened that night later.

Anal sex first showed up on my radar during my junior year when Eric obtained several really hard core anal sex videos from a friend. He told me about them during school and I agreed to come over and check them out after school. That was the first time I was really exposed to hard core pornography. I remember seeing images of DP, Ass to mouth, cum swapping, it was really hard core stuff.

I was still relatively innocent at the time and I watched the videos the way someone might watch a contortionist or sword swallower, with shock and intrigue. The scenes depicted rough anal sex with the guy slapping, choking and pulling the hair of the gal while violently fucking them up the ass.

There was one scene in particular that Eric raved about. It consisted of this guy with an incredibly huge cock whom I would later learn was Rocco Stiffredi painfully taking this girl in the ass. The girl was obviously in pain during the act and trying to push him away. I was a disturbed by it but when I snapped out of the trance by the shocked of what the girl was going through, I noticed Eric and saw that the footage was having a totally different effect on him.

His eyes looked glazed with desire and he actually had his jeans unbuttoned and had his hand in his pants masturbating while watching the scene. "Eric" I screamed when I saw him playing with himself. "Jenny this scene is so hot. I can't help myself, I wish I was that guy giving it to her." Eric declared. "Come on Jenny give me a hand" He reached for my hand and wanted me to help masturbate him. We had fooled around before then. We've made out together, I've jerked him off before and once even tried giving him a blowjob but under the present circumstances I wasn't going to accommodate him.

Eric actually pulled it out then and continued to masturbate to the cries of the girl on screen being savagely fucked in the ass. The man pulled out of the girl's ass and came on her face and in her mouth making her suck his cock straight from her ass. About the same time Eric came ejaculating over himself. I decided this was a good time to go home leaving Eric with his videos.

From then on Eric had a huge fetish for anal sex. He watched more and more hardcore anal sex vidoes some of which I watched with him. His favorites consisted of huge cocks, petite girls and painful anal sex ending in ass to mouth cum shots. He seemed to revel in the sight of a girl writhing in pain from a huge cock up her ass. It was a sadistic side of him I had never seen before. He wanted to know what I thought of the movies and if they turned me on. He wanted to know if I would have anal sex with Joey my boyfriend at the time if he asked me. He kept trying to get the girls he dated to let him try it but they all refused to accommodate him. He even begged and pleaded with me to try it with him. He would tease me "Cmon Jenny, you have such a hot ass. Let your big brother have it". I would always reply coyly, "You want to sodomize your little sister? That's so wrong!"

Beginning of senior year things took a turn for the worse for Eric. His mother got a new boyfriend whom Eric couldn't stand. He was staying at their house a lot and many a night Eric would storm out of there after a fight and end up crashing at my house. My mom would let he stay in the guestroom.

That summer before our senior year Eric fell madly in love with this cold hearted girl whom I personally couldn't stand but he was crazy about her and kissed her butt. It was the first time he fell in love and he fell hard. A week before his 18th birthday she broke up with him to go out with some other guy leaving him devastated. To make matters worse his mom went off with her jerk off boyfriend on vacation even though her son's birthday was that week. Her excuse was it was the only time her boyfriend could get off work.

He told me perhaps he'll just drop out of school and move out on his 18th birthday so his mom could snuggle up with her boyfriend 24x7. He was really depressed. He ditched school and just stayed home by himself. I felt really bad for him and wanted desperately to cheer him up. That's when I came up with the idea. It was something I knew Eric had been dreaming about for a year.

I put on one of the sexy outfits that Eric had gotten me. It consisted of a mini skirt high heels and a half top that showed my naval. I even did my hair up and put on a lot of make up. I showed up at his house that evening looking like Suzy Slut with an exquisitely wrapped present.

I could tell he was depressed but his face lit up when he saw me. "What's this?" he said, "Why are you all dressed up, are you taking me somewhere for my birthday?" I said "No, you know I'm broke, can't I dress up for my big brother on his birthday?" He gave me a big hug and said "You can dress up for me anytime lil sis, you look great but if you dress like that I don't think I'll be able to keep my hands off of you!" as he playfully groped me. "Thanks for being here, I can always count on you Jenny" he said hugging me again.

I gave him the present and said Happy Birthday Eric, open it. He said "Thanks Jenny, you are a sweetheart." He unwrapped the present and opened the jewelry box that use to hold and bracelet only to find a tube of KY jelly. He looked at me with a puzzled look on his face. "That's only the first part of your present" I responded trying to sound coy but instead sounded nervous. "Here is the second" I was pretty nervous at this point. I had rehearsed this several times at home in front of the mirror. I hope it would have the desired effect and that he wouldn't just laugh at me.

With that I turned my back to him, bent over at a 45 degrees, pushed my butt out provocatively towards him and lifted up my skirt to reveal my bare bottom with no panties on. His look of puzzlement quickly turned into one of surprise and then desire. I let out my breath satisfied that it had the desired effect. I then stepped back up against him and rubbed my bare bottom against his crotch.

Now remember we were teenager, neither one of us had any experience with anal sex other then what we saw in porno movies. Add to that the highly excited, over zealous state of teenage boys and my nervousness, that doesn't exactly equal a recipe for successful anal sex. Lets just say the first time the head of his cock penetrated my anus, I screamed in pain and pulled away from him. I cried I'm sorry Eric, I can't do this. Go wash and I give you a blowjob instead and I'll let you come in my mouth knowing that was another big fetish for him.

I saw the disappointment in his eyes as he turned around to go to the bathroom to wash. I gradually regained my composure and I began to feel really bad. I had come over here to cheer him up on his birthday and now I was going to let him down too. When he came back I knelt down and took his cock in my mouth and sucked him a few times. It was then that I decided come hell or high water I was going to go through with what I had come here to do. I took him out of my mouth and to his surprise took the KY jelly and began rubbing it on his cock.

The second time he penetrated me anally I howled in pain but I gritted my teeth and endured. Lets just say the night ended with Eric having my forbidden fruit and experiencing the best sexual experience in his 18 years of existence and me having a tear stained face and a very very sore bottom. Doesn't seem fair does it. See how much I love you Eric!

In retrospect as I am writing this now I realize my motives were not totally altruistic. Its true that I loved Eric and really wanted to give him something special for his 18th birthday and I really felt bad for him and wanted to cheer him up but those were not my only motives.

We were both sexually active by that time and I had already been with several guys. Eric and I fooled around a little during early adolescence but it was more the "I show you mine if you show me yours" type. We did a little mutual masturbation and I had tried once to give him a blow job but really it was more like a couple of licks and a bad attempt at sucking.

Up until that night Eric and I had never really had sex together. For me it seemed that I was physically intimate with guys that I really was not that close to yet Eric whom I've knew forever and shared all my thoughts and feeling with I had never shared my body with. I guess a part of me longed for physical closeness to the one person I felt emotionally closer to then anyone else in the world. That and I was just a little bit curious about anal sex since Eric talked about it all the time.

After that night Eric was obsessed with having anal sex with me again. He begged, pleaded, cajoled, blackmailed, and guilt tripped me in an attempted to have me again. After about 3 month of this I finally broke under the pressure and conceded in letting him have me anally again. About 3 weeks later a third time and then a fourth, and a fifth and so on. Lets just say I spent my senior year with a major pain in my ass literally.

It was during this time that I gradually began developing a taste for this painful sinful pleasure. Anal sex for me was and still is a dichotomy. Its something I loath and love at the same time, fear it and desire it. It's a lust for pain and pleasure. To me it is the ultimate submission of myself to a man. To me there is no doubt that anal sex has S/M connotations to it and I discovered that there is definitely a submissive masochistic streak in me.

As much as Eric didn't like to admit it he definitely got off on rough anal sex with me and enjoyed hurting me with his cock. For one who is normally so protective of me like a brother, it never cease to surprise me how when he is overcome with lust, he become sadistic and my cries, moans and tears only seem to fuel his desire. I remember once asking him about this stating "Do you enjoy hurting me during anal sex?" He had responded after my continuos prodding with yes I guess it turns me on a little bit.

I had responded with you are a sadist who enjoys hurting his little sister and best friend. I could tell that label did not sit well with him and his role as my surrogate brother and best friend. He became very uncomfortable at my accusation. I let him sweat for just a little bit before moving in, hugging him and whispering in his ear, it's ok big bro, I kinda enjoy being hurt by your cock. Feel like hurting me a little? I'm sure you can imagine what happened next.

It is also during this time period that I perfected my oral sex techniques. I learned how to swallow. Semen is an acquired tasted and even then it's not exactly delicious. It smells like bleach and has a strong after taste but the power the act of swallowing has on a man makes it so hot and sexy. It is his seed, from his cock, a product of his lust and desire for me that I take in my mouth and swallow. That's makes it hot. For us women it's all mental and after discovering my submissive side there is definitely something very submissively sexy about kneeling in front of a man taking his cock in his mouth pulling it out when he is about to come, opening my mouth, sticking out my tongue and deliberately letting his cum into my mouth in his full view.

The first time I tried swallowing I had taken Eric out of my mouth and let him cum on my tits. When the spurts subsided I licked the cum off his cock head. It wasn't that bad so I decided to scoop some of the cum off my tits and put it in my mouth. In the end I had scooped up all his cum off my body and swallowed it. I was quite proud of myself even though I felt queasy afterwards from the after taste.

Cum and swallowing was another one of Eric's big fetishes and he coached me through this as a substitute for when my bottom was simply too sore to take him again (His lust for my ass recharged faster then my body could heal) or if I just wasn't in a mental state to deal with the pain of anal sex. He absolutely love it and it was second only to taking my anally. I loved looking up into his eyes watching him watching himself come in my mouth. I have tried this technique on several other men since and it has never failed to drive them absolutely crazy. I guess having a girl swallow cum seems to be a universal fetish for men.

It was also during this period that the very first anal scene of the Rocco painfully taking the girl anally started becoming my ultimate fantasy. My original feelings of shock, intrigue and repulsion was gradually replaced with, longing, lust and desire. I imagined I was that girl except in my fantasy I had my hand handcuffed behind my back so I would not be able to push him away. I would bend over the bed with my hands behind my back offering myself to him. I would tell him to use me for his pleasure, to force me to take every inch of his cock. I imagined him taking me mercilessly with that big sexy cock of his. I wanted to feel every inch of it in my body, in my ass painfully fucking me. More often then not I would masturbate to this fantasy.

I confided my fantasy to Eric and he was very excited by it. He asked me if I could take a cock that big and if I could take the pain. In my fantasy world I was free to take all pain and pleasure I could imagine but if it was really going to happen I told him I honestly didn't know but it would be the ultimate anal sex submission.

Shortly after that he showed up with a pair of handcuffs and handcuffed my hands behind my back. Then he proceeded to take me anally with me absolutely helpless. I really could not do a thing. It was a very erotic vulnerable position. My face and tits were planted firmly on the bed since I could not support myself with my hands behind my back. My butt was pinned by his cock as he savagely took me. We still use the handcuffs from time to time when he feels the need to completely dominate me.

The year ended and we both went away to college. We kept in touch over email and phone calls. We still confided to one other about everything. I had several different boyfriends in college but only one had been interested in anal sex. We did it a couple times and then broke up.

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byjennyX1984© 25 comments/ 168444 views/ 34 favorites

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