Painful Lesson - Cover

Painful Lesson

by Kimberly Parker

Copyright© 2006 by Kimberly Parker

Erotica Sex Story: A young man learns the secrete of pleasing a woman the hard way

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   ft/ft   Consensual   Gang Bang   .

It was Friday, my bowling night, and as usual the five of us would stop off in the lounge afterwards to have a few beers and hopefully score with some chicks. I watched, as a few hot young girls would move up to some guys, who quickly bought them a drink, and not long after they could be seen leaving the bar together.

Girls' picking up guys was like fishing in a fish tank, quick and easy even for those who weren't "super models". Rick, as usual, hit it off with one girl and the two were soon leaving together, as did Justin, while the other two and I two kept striking out over and over again.

It wasn't long before they also were over in a corner booth with two lovely ladies, while I was left along at the bar sipping a beer. Damn I was horny, and it was sort of pissing me off that I had so much trouble getting laid lately. I don't know just what the problem is; I am pretty good looking, so I have been told. Still had the athletic body I had while playing sports a few years ago in high school, and my clothes are neat and in style, so what is the problem.

It seemed that was all I had on my mind as of late, getting laid, and then getting laid again. These girls, they could it anytime they wanted. It wasn't fair. Nature should turn it around, and have the women chase the men. Yeah, that would be cool, and then I could get it everyday, maybe twice a day for that matter. Yep, that's what I would like, have sex anytime I pleased.

Suddenly a tall sexy woman with long black hair came up and sat down and smiled. Wow, was I about to get lucky, or was she just killing time, or wanted a free drink.

A few moments later, she moved closer and put her arm around mine and whispered. "I think I know, no, make that I do know what's on your mind, and I can take care of that for you if you wish."

She was one hell of a sexy chick, and if she really knew what I was thinking, then I was certainly ready let her take care of things. She turned to the bartender and ordered another couple of drinks, one for her, and the other for me. I usually drink just beer, but if this was her way to getting things started, then by all means I would have whatever she ordered.

After we finished off the drinks, she took my hand and led me outside to my car, but instead of getting in, she pressed my lips to hers and began driving me slowly out of my mind. I felt my cock start to come alive, and I guess she did also. She pressed hard against me as her tongue explored my mouth she began to unzip my pants. She mumbled something about knowing I couldn't wait any longer, and pressed her mouth hard against mine. It felt like her tongue went all the way down my throat as she kissed me and stroked my cock. I felt like I was having trouble breathing and tried to pull away, but she held me tight. Finally she pulled her lips from mine and dropped to her knees.

My head was spinning and my whole body was trembling as she gave me the most sexual pleasure I had ever experienced, and right there in the parking lot. Suddenly she stood up and kissed me again gently and pulled away. I looked at her, and couldn't help but notice her eyes were sort of a reddish orange color. Just what the hell was in that drink, some sort of hallucinating drug? I closed my eyes and leaned back against the car for a second or two, and everything was a blur.

I awoke the next morning still a little groggy from whatever was in that drink, and really couldn't remember driving to my apartment. I slowly opened my eyes to very familiar surroundings, but it wasn't my apartment, I was in my old bedroom at my mother's house. I must have been so messed up to have I forgotten that I had moved in to my own place a few months back and instinctively drove here.

I didn't have one of those head pounding hangovers, but I still felt a little groggy, and figured a cool shower would wake me up. After about ten minutes or so, I climbed out of the shower, grabbed a towel and began drying off. The cool water felt good, but I knew another couple hours of sleep were what I really needed. I wrapped the towel around my waist and turned to open the door when I got the shock of my life. I stared at the reflection in the full-length mirror, and saw a girl standing there, a young girl with perfectly shaped breasts. What the fuck?

I suddenly felt really weird and leaned back against the wall with eyes closed and thought that whatever I had last night was still with me. When I opened my eyes, it was still a pretty young, and naked, girl in the reflection. I stared at the reflection as I placed my hand over my chest, and found that I had tits, nice tits, but tits just the same. I removed the towel stared at the light brown bush between my legs, but no cock.

I moved back to the bedroom and fell back onto the bed rationalizing I was having a really crazy dream, or I was hallucinating. Although I had never experienced LSD, I heard it did things like that, an assumed that was what was in my drink last night, and it still was affecting me. I closed my eyes for a few moments to rest when I heard a familiar voice.

"Patti, come on girl get dressed. We're going to be late for detention. Mr. Ashton will make us serve another one if we're late, so come get your ass out of bed and get dressed."

I opened my eyes, and standing there at the door was Jessica Adams, my friend Rick's hot and sexy sister, a girl I lusted for all through high school. Realizing that I was lying on the bed completely naked, I grabbed the blanket and covered up. I looked at her and wondered why she called me Patti. Why, my name is Patrick.

"Jessica! I'm not dressed."

"Yeah, so what? I see you naked everyday in gym class, so don't be so modest and get up and get ready."

For some reason I knew I had to be at school, but why? I graduated four years ago but I did as Jessica ordered. I turned towards my dresser, and instead of the old rustic looking one I had; this was pink with teddy bears painted on the drawers. I looked up at the shelf that held my sports trophies, but now there were stuffed animals. The wall that had the Sosa, McGuire and Jordan posters, now had picture of those fag boy bands. Holy shit, what a dream I was having.

I opened the bottom drawer and pulled out a pair of pink cotton panties and slipped them on, then the top drawer for a bra and t-shirt, and finally the second drawer for a pair of tight fitting jean shorts. How the hell did I know where everything was?

As Jessica and I walked towards the school, I suddenly began to remember us being caught sneaking out of class early, and that was why we had Saturday detention. The more Jessica talked, the more I felt this was all real.

During the three-hour sit and shut up class, I began to feel pissed off that we had to spend the last Saturday before the school year ended in detention, I mean couldn't it have been overlooked so close to the end of class for the year?

When the class ended, Jessica grabbed my arm and tugged. "Come on, let's get out of here. Hey since it's kind of hot out today, why don't you stay at my house for while and we can lie on the pool deck and get a head start on our tans."

The thought of seeing Jessica in a bikini gave me a little shiver, and quickly agreed. When we got up in her room, I remembered I didn't have a suit.

"Jessica, I don't have a suit or anything to wear."

"Don't worry, I got more than one suite, you can use one of mine."

I stared at her as she shed her clothes and was now standing just a few feet away undressed as she had been in my thoughts those nights I jerked off. She noticed I was staring and put a hand on her hip.

"Well, you going to undress or what, and why are you staring at me? Something wrong?"

"Ah no, it's just you got one hell of a sexy body. Perfect tits, tight ass, and those long luscious legs."

"Well thank you Patti, but I don't think a girl should be saying that, unless you're, you know a lesbo or something."

I felt little tremors in my jeans as I looked at her and had the urge to grab her and throw her on the bed and fuck the shit out her. Thoughts of slipping my cock deep in her pussy filled my head as I put on the suite she gave me.

During the next week I attended school and everything felt normal, except I knew it wasn't. I was Pat, not Patti and it was all a crazy nightmare.

A few days after classes had ended, Jessica and I were up in her room talking about guys, how sick. She said she had a crush on Justin, her neighbor, and last night they had a heated make out session.

"You wouldn't believe it Patti, Justin got so worked up he started to grind up against my leg, like, you know fucking me. You believe that?"

I smiled, knowing a lot of guys did that, and well at least I did, and thought nothing of it.

"Jessica, that's because you're such a hot girl you got him to point to where he needed relief. He probably shot off in his shorts. You should have sucked him off, or at least given him a hand job."

"Sucked him off? Are you nuts or something? Yeah, maybe a quick hand job, but why would I ever give a guy a blow job?"

"Well, maybe he would return the favor and go down on you. You like to cum don't you, and I am sure if he went down on you, you would have."

Jessica just sat there quiet.

"So, am I right? It feels good to cum, and don't you get in the mood when you make out?"

"I guess, but I really don't know what it's like. I mean a couple of times I, you know, used my finger to see what it was like, but never with a guy."

"You mean to tell me a guy has never eaten that beautiful cunt of yours. Holy shit Jess, you need to do that sometime."

"Have you ever had a guy do that to you?"

How was I to answer that? A guy, no way."

"Well, sort of, but it wasn't a guy."

"What!! You mean a girl did it? How gross. I swear Patti, you're sounding more and more like a lesbian. Are you? You like girls more than guys?"

The answer was yes, but I certainly couldn't tell her that.

"No, not at all. It just happened one day, and I loved it. It felt great, and she never, or did I, do it again. I think it's different than two guys, that's gross as hell, but a girl knows what another girls wants."

"Damn Patti, I never would have thought you would let another girl do that to you. Wow, but what was it like?"

"Well, you said you used your finger a few times, but this is a thousand times better. Plus you don't have to worry about some guy bragging to all his friends; you know what they are like? If you want, I'll try it on you, I mean I think I know what to do, even though I have never did it to a girl." I lied

"Oh I don't know Patti. What if I liked it and turned into a lesbian or something?"

I could tell she wasn't all that apposed to the idea, and I was watering at the mouth to taste that sweet slit between her legs.

"Well, I would hope you would like it, but that wouldn't mean you are a lesbian. It's just a better way to cum than a finger."

She was a little reluctant, but finally allowed me to ease her on her back and I slowly slid off her jeans and panties. I could feel her tighten up as I pushed her legs apart and gently massaged her inner thighs. I heard her say I should stop, but once I ran my tongue over the length of her slit, she protested not more.

After I had made her cum, she instantly felt ashamed at what happened, and quickly grabbed her clothes.

"Oh shit Patti I can't believe what happened. I need to take a shower."

As Jessica disappeared into the bathroom I slipped off my shorts and shoved my hand inside of my panties. I quickly attacked my clit only to find I didn't receive the pleasure I thought I would, and actually it felt too sensitive to touch. I then pushed two fingers inside and felt the pain right away. Damn, I was a virgin, and that hurt.

That evening I got in bed and began thinking about what happened earlier with Jessica, and ran a hand over my crotch. I closed my eyes and fantasized it was Jessica that was rubbing my cock to hardness. I began to fell the wetness form between my legs, and continued to soft gentle touch over my cock, or cunt, whatever.

I ran a finger the length of the slit, and pulled the juices up and over the little nub and felt the tingle though my body. I worked it slowly, not like the way I used to jerk off, but slow to make the feeling last. It took over a half hour before my body shook with pleasure, a pleasure I never experienced in the past.

Well, since I was a girl, at least in my dream, why not enjoy it and have as much sex as I wished. Getting someone to have sex with is easy, if you're a girl, and right now I was. Of course that meant getting it from a guy, but in a dream, what the heck.

About a week later Jessica and I were up in her room just hanging out and talking about guys, or at least she was. She admitted getting her pussy sucked felt great, and wondered just how she could get Justin to do that to her.

"Like I told you Jess, next time you two get a chance to be alone and make out, start by giving him a nice slow hand job. Afterwards, tell him you'll do that, and more, if he takes care of you. Of course more means sucking his cock, but I bet after that, he'll eat you whenever you ask. Once he tastes that sweet pussy of yours, he'll think of nothing else."

"Patti, I don't know if I could, you know, suck a boys cock. What happens if I got him so worked up he starts to cum, then what?"

"Keep sucking slow, and swallow it, all of it. Guys love that. You'll have him eating out of you hands after that, and eating something else if you know what I mean."

"Swallow!! How fucking yucky it that? I would be totally grossed out just by having it all over my hand, and you're telling me to let him shoot off in my mouth, AND SWALLOW? I don't think so."

"That's exactly right. Besides, you won't be the first, or the last girl to do that. Who knows, you might learn to like it, and I know Justin would and if he is a normal guy, he'll be more than happy to eat that tasty pussy of yours at a drop of the hat."

"Tasty? You think it is tasty?"

I was getting so fucking worked up talking and thinking about Jessica's cunt I spoke before thinking.

"Oh fuck yeah Jessica. Your cunt is delicious and I could eat you every day of the week, and twice on Sunday."

Jessica just looked at me, and before she could say a word there was a knock on the door.

The door opened and standing there was Jessica's brother, Ricky, my best friend since the fourth grade.

"Jess, mom and dad went to visit uncle Jim and aunt Carol and left money for us to get something. I'm starved. Want to walk to the Patrones and get a pizza?"

Rick then looked at me and smiled.

"Hi Patti, you're looking really hot lately. You want to have something to eat to? You can come with us."

I busted up laughing at what he said and looked at Jessica and saw her trying to hide her smile.

"Sure Rick. Jessica and I were just talking about eating something, so yeah I'll go with, and that's if you really don't mind."

By the time we got back to Jessica's house it was almost 10:00 and I thought it was about time I went home, but Jessica encouraged me to call home and tell my folks I was spending the night at her house. I thought about it for a minute or so and finally agreed. I really wanted to go home and finger myself, but the thought of being in bed with Jessica was too much to pass up.

I pulled off my jean shorts along with my t-shirt and bra and pulled back the covers to get into the double sized bed and Jessica just looked at me.

"Patti, you're going to be like that, just panties and nothing else?"

Well that was how I normally sleep, in my jockeys only and, well it was normal for me.

"Sure, why not."

"Well, I just thought you would at least leave on your shirt, that's all."

Jessica turned off the lights and moved into the bed and once again started to talk about Justin and the conversation we had earlier.

"Patti, be honest with me. Have you ever did that to a guy, you know, suck him like you said I should do?"

Her words should have repulsed me, but for some reason it didn't. I mean me sucking a guys cock should have grossed me out, but it didn't.

"No, but I would if I had the chance, especially if it meant he would do me. I love to cum, and would do anything to make that happen. Every night before I go to sleep, I get myself off, I can't help it, it feels so good to cum, but doing it alone sucks."

"Every night?"

"Just about. I don't know why I am like that, but it seems like I am always in the mood. I close my eyes and I think how good it feels, and bingo, the next thing I know I am getting all worked up. Like now, talking like this is getting my nips hard and I feel a tingling sensation in my crotch."

"Are you saying you want to cum?"

"I always want to cum. Like I said it feels so good, I want it all the time. Why do you ask?"

Jessica sat up and took a deep breath before speaking.

"Well, I have to admit it did feel great when you did it to me, and I am in the mood for that again, and if you want, I'll try it on you."

Holy shit, Jessica was offering me sex. I couldn't pass that up, even with out a dick to slip in her.

"Really? Oh yeah, I think I would like that, but let's do it together, do each other at the same time."

I pulled the covers off of us and began to caress Jessica's firm breasts for a moment or two then leaned over and gently rolled my tongue over her hardened nipples while my hand stoked her inner thighs. Her legs parted as I slid my hand over her panty-covered cunt as I moved to her other leg. I felt her hand trying to get to my breasts that were pressed against her, and I rose up a bit to let her gain access.

Without saying a word, the two of us slipped off our panties and touched and caressed each other, as we wanted to be touched. I was ready, but I wasn't sure about Jessica, and I waited for her to give some sort of hint it was time. When she began to purr like a kitten I moved up and placed my lips to hers. She retuned my kiss with passion, and I knew she was fully ready to move on.

I turned around on the bed and grabbed a pillow and placed it under my head and urged her to move on top of me, each of us facing opposite directions. I softly licked her dripping slit, and after a few moments she did the same to me.

I savored the sweet juices that were flowing from her cunt and slowly moved my tongue to her exposed clit. Soon she was grinding her cunt against my mouth as she sucked and tongued me. I felt her body tremble and knew she was close and I sucked her clit hard, bringing her over the edge. Seconds later I felt the explosion inside of me and we both were moaning in pleasure.

Although I enjoyed eating her, and did feel pleasure of her eating me, I wanted real sex. I wasn't repulsed by the fact of having a cock inside of me, it was just the opposite, I craved it.

Jessica was still breathing heavily as I moved up next to her and softy ran a hand over her breasts, keeping her in the loving mood we had shared.

"Oh that feels so good Patti."

I leaned over her face and pressed my lips to hers and I felt her passion begin to rise once more. When the kiss ended, I rested my head back on the pillow, taking deep breaths, and then I heard her whisper.

"Patti, are we lesbians?"

"No, I don't think so. You like guys don't ya. I mean wouldn't you want to do this with Justin?"

"Oh sure I would, but I really enjoyed this tonight. How about you, isn't there a guy you want to do it with?"

"No one in particular, but you know, we should find two guys who would be willing to have a little fun. I am sure Justin wouldn't turn it down, and if it didn't freak you out, I could hook up with Ricky."

"Holy shit, with my brother? I know he would love to get it on with you. I overheard him a few times talking with Justin how hot you were. Yeah, he would."

"O.K., now that we know who we want to try it with, the next thing is to figure out when and where."

Although we hadn't anything planned on accomplishing our mission, the following Saturday provided the opportunity. Jessica's parents were going to a wedding of a girl that her mother worked with, and since neither Jessica or Ricky were going, they would be home alone for at least eight hours.

 
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