Losing It - Cover

Losing It

Copyright© 2006 by Just Plain Bob

Chapter 1

Erotica Sex Story: Chapter 1 - A young man's desperate attempt to lose his cherry has unexpected results.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Consensual   Reluctant   Blackmail   Heterosexual   Cheating   Incest   Mother   Son   Brother   Sister   Gang Bang   First   Oral Sex   Cream Pie  

You remember when you were a young teenager, still a virgin, and with all of those raging hormones? The only thing important to you then was getting rid of your cherry; finding some girl willing to play 'doctor' with you, willing to let you lift her skirt and lead you to the Promised Land?

Remember how you felt when your buddies would tell you that they had gotten laid? Remember drooling as they recounted each and ever juicy detail? Remember getting the name of the girl and hitting on her and being told to "Fuck off asshole?"

I was eighteen, still a virgin, and it sucked!

I live with my mom, dad and older sister. Mary is two years older than I am and early on we had agreed to despise each other. I'm told that this is common in families where there is an older sister and a younger brother, but I've never seen it in any of my friend's families. Whatever, Mary was in her third year of college and I'd heard mom and dad commenting on the crowd that she was running with. Frankly, I was surprised they noticed, but then what kid thinks that his parents know anything. The fact was that she was running with a pretty rowdy group and more than once I'd seen her sneaking into the house after going out and partying. I knew that she was drinking heavily and although she didn't smoke she did do some weed. I didn't have a clue as to how bad she really was until one weekend when my parents left town to visit relatives.

I was supposed to spend the weekend at my buddy Ron's house, but we got into an argument and I stormed out and went home. When I got there the joint was jumping. Mary had apparently interpreted mom and dad's "You are not to have anyone over while we are gone" to mean that 'anyone' was singular and that therefore everyone (plural) was okay. I hung around outside and watched the comings and goings and looked through the windows to see how college kids partied. It didn't seem to be too much different from the parties that me and my buddies had except that instead of just beer there was some hard stuff and apparently plenty of weed. The girls seemed to be a lot wilder too. I saw a couple that seemed to get a charge out of flashing their tits and I wondered if I went in how long I could last before Mary saw and had a cow.

Then I noticed that I didn't see Mary anywhere and when she hadn't made an appearance after ten or fifteen minutes I decided to crash her party. I walked in like I belonged there (which in a sense I did), grabbed a beer out of an ice chest and then I just mingled. I hadn't been there two minutes when one of the girls that I'd seen earlier came up to me and said, "Hi, I'm Jan. You're cute, want to see my tits?" and she lifted her sweater. Right behind her came the other one I'd seen and she hoisted up her sweater and said, "Mine are better."

I stood there looking from one to the other and thinking that I'd died and gone to heaven. Then Jan said, "What do you think, are mine better than hers?"

I smiled and said "The only way I can honestly judge them is to taste them" and I stuck my tongue out and leaned forward.

Jan pulled down her sweater, snarled "Pervert!" and turned and walked away. The other girl gave me a nasty look and then took off after Jan and I heard a couple of guys standing near us say "Way to go dude."

I headed up the stairs to my bedroom and walked in on a couple who were fucking on my bed. The guy gave me a nasty look and said, "What the fuck are you doing in here?" I ignored him and went over to my dresser and got the present that I'd received for my seventeenth birthday out of the top drawer. It was an Olympus D-370 digital camera and I loved it to death. Take a picture, plug the camera into a USB port on a computer and - viola - instant pictures. Just what I needed to get the photos that would give me leverage over Mary.

The guy on the bed said, "Hey asshole, I asked you what you were doing in here!"

I turned to him, "This is my bedroom dick breath and I don't recall you asking me if you could use it" then I raised the camera, said "Smile" and took a picture of him and the naked girl on my bed. While he was still trying to figure out what had just happened I left the room.

I went back to the party and started to take pictures. A half-hour went by and I still hadn't seen Mary so I went back upstairs and started checking bedrooms. There was a different couple in my bedroom and they ignored me when I looked in. The spare bedroom had two couples on the bed and I quickly backed out and left them alone. There was another couple on the bed in Mary's room and when I opened up the door the girl giggled and said, "Oh good, reinforcements."

I was tempted, oh God was I tempted, but I was after blackmail material and I had temporarily forgotten how bad I wanted to lose my cherry.

It was in mom and dad's bedroom that I hit pay dirt. There in the middle of the king size bed was Mary - and three guys! I was so surprised that I froze in the doorway and lost valuable seconds. One of the three guys turned and yelled, "Get the fuck out of here" and that woke me up and I started snapping pictures as fast as the camera would go. I got seven before two of the guys got off the bed and came for me. I ran laughing from the room and left the house to go for a walk and to let things settle down. Twenty minutes later I went back to the house and I hid the camera in the garage. I went back inside the house, got a beer and started mingling again.

I was having a good time. I was sipping a beer and a couple of girls had pulled me out onto the impromptu dance floor and I began to entertain the idea that I just might lose my virginity if I played my cards right when out of the corner of my eye I saw Mary. She was standing off to the side and I saw murder on her face. Any other time I would have been terrified, but not now so I ignored her. Ten minutes later I was in a quiet corner necking with one of the girls I had been dancing with and to that point she hadn't made any objections to my roaming hands. I was seconds from asking her if she wanted to see my room when Mary walked over to us and said to the girl, "You know that my little brother (and she emphasized 'little') is only eighteen, don't you?"

From the look on the girl's face I sensed that she could have cared less, but I could also see that she realized that there was some "family shit" going on and she wasn't going to get in the middle of it. She excused herself and walked away. I looked up at Mary as she stood there with a self-satisfied smirk on her face and I thought to myself, "Okay bitch, you asked for it!"

Now you need to understand that I never planned on showing my photos to my parents nor did I plan on telling them about Mary's party, but the bitch had just killed my best shot at getting rid of my virginity. I was mad; I was really, really pissed and it showed when I said, "Congratulations on winning the Dumb Shit Of The Month award. I only intended to have some fun with you with the pictures that I took to get even for some of the shit you've pulled on me over the years, but now you have gone and pissed me off. The only question now is do I call mom and dad now and tell them about this party or do I wait until they get home, tell them and then show them the pictures? No, there are really two questions. The other is do I just show the pictures to mom and dad, or do I post them all over campus and put them on the Internet?"

Mary's face drained of color when the realization of what she had just managed to accomplish hit her. I turned and started to walk away but she grabbed me, "Wait! I'm sorry. We can work this out, can't we?"

"I don't see how."

Mary got a determined look on her face and in a flat voice said, "What do you want?"

Actually I had been too pissed to consider getting something from her, but then inspiration hit me for the second time that night, "You just fucked up my best chance yet of getting rid of my cherry. You see to it that I get laid tonight and I'll give you the photos I took tonight, help you clean the place up after the party's over and promise that mom and dad will never find out about it from me. But if I'm still a virgin when the sun comes up tomorrow mom and dad WILL see the pictures and I swear that I will post the ones of you and three guys all over town."

"Just how in the hell am I supposed to get you laid?"

"Well you managed to find a way to keep me from getting laid so I guess you will just have to find a way to reverse the process. Just remember - laid by sunrise or you are fucked."

I really didn't expect her to roll over and she didn't disappoint me. I was standing in a corner sipping a beer and watching the girl I had hoped to take up to my room walking up the stairs with some one else when three guys walked up to me. "Give us the camera asshole."

"I don't think so."

"You don't seem to understand you little dip shit. You will give us the camera or we will hurt you."

"No, you don't understand. If you hurt me that will be just one more thing that Mary will have to explain to our parents when they get home."

They looked at each other, finally figured it out and went looking for Mary to give her the bad news.

The party began to run out of steam and people began to leave. At three-thirty in the morning there was only Mary and I and the mess. I was sitting in the kitchen eating a sandwich (beer always makes me hungry) when Mary came in and sat down at the table.

"What else can I do to keep you quiet?"

"I told you. Laid by sunrise or you are toast."

"I tried. Honest to God I tried and there were even a couple of girls who would have done it if it wasn't for your age."

"Yeah? And just how did they find out about my age, or did you forget that part?"

"I'm sorry."

"Sorry doesn't cut it Sis" and I got up and went up to my room. By then I'd had a couple of hours to get over being mad and I wasn't going to blab to mom and dad, but I wasn't going to tell Mary that. Let the bitch sweat until our folks got home.

I'd been in bed about an hour when the bedroom door opened and then closed. A moment latter some one got into bed with me and a hand slid down my body and found my cock. As my cock leapt to attention I wondered who it was that Mary had found to take care of me. The hand stroked me a few times and then the person in bed with me shifted position and I felt something hot and wet surround my cock. I suddenly realized that I was getting my first blow job. The hot mouth slid up and down my cock and a hand caressed my balls and I wanted to turn on my bedside lamp so I could see who it was giving me all that pleasure. By the same token I was afraid to move for fear of causing it to stop. A couple of minutes passed during which I tried to fight off cumming because I didn't want her to stop, but she must have wanted to get it over with because suddenly a finger was pushed into my ass and I exploded like a volcano. I expected her to jerk her head off my dick, but she didn't. Her hands squeezed my balls as she milked me for everything that she could get out of me. My cock started to go soft and she took her mouth off of it and licked it a few times and then she said, "I don't usually swallow, but losing your cherry should be something special."

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