It's hard being a senior in high school, especially when your older brother was a sports icon. Many think it would be easier, but let me tell you, it is anything but.
The coaches think you have sports talent, but I didn't. The teachers think you can replicate his book knowledge, I can't. And the girls that flocked to his side, well, their younger sisters would have nothing to do with me.
It's not fair, but it was reality.
My best friend Dan and I would discuss everything and anything. We'd double dated a couple times, and he even tried to get me a date with his sister but she'd have nothing of it. On those hot days, I was joined in my bedroom by Dan to spy on the girls who loved sitting out by their pool and soaking up rays.
Sometimes their tops would come off, but hardly ever in a way that we got more than a glimpse of breast. It's like they had special antenna that went up when we were watching.
When we were lucky enough to hit the jackpot, and get a view of perky teenage tits, we both not only smiled but grimaced. They were so beautiful. To be honest, I had fondled Lisa Gentry's boobs both over and under her top, but had never really saw them with anything other than my hands. Dan did admit to seeing, and licking, Mary Bartholomew's boobies on several occasions before they broke up.
Still watching Jennifer, his sister, or friends Courtney and Amber, bare their 18-year-old boobs on those infrequent occasions was quite the erotic treat.
There was a warm Tuesday when I was home early from school where I got a special treat. Dan's mom was out back, sunning, wearing only a bikini bottom. Her large breasts were fully on display when I peeked out of my window.
At first I was shocked, but my brain told me the 40-something woman deserved an all-over tan as much as her daughter. I stared at her, lust in my brain, for more than a half hour. That night I jerked off thinking about the MILF, she replaced her daughter as the focus of my nocturnal ministrations for the next several weeks.
Oh, I still thought of Dan's sister Jennifer in my late night activities, and once even had the two of them in a three-way tryst. Ah, the mind can really expand when women are in the middle of things.
I finally did get a date with Jennifer, a couple of weeks after she broke up with a blowhard full of himself guy named Bill. It was a sort of, well, mercy date. Dan convinced her it was good to get out on dates, and she really wasn't over Bill. So I became the perfect stand-in, just like in the movies where the star doesn't do the stunts, his double does.
We went to Sonic for burgers the first time, and it actually was fun. She gave me a good night peck on the cheek that I rubbed in and later rubbed off to. Our second date was to the movies, were I conveniently put my arm around her to hold her close during the scary scenes.
That night I dropped her off, getting a nice smooch on the lips. I tried for a little tongue, but there was an iron wall there and my lips never got past the gate.
During the week I'd attempt to spy on the girl and her mom when she sunbathed, never catching bared breasts but still loving every nook and cranny I could see. She'd lower her bikini bottom a little for more sun, and I loved the new (to my eyes) inch it displayed.
That looking got me in trouble, though, as the next afternoon Mrs. Johnson, Dan and Jennifer's mom, smiled at me and said hi on my way home from school.
"Where's Danny," asked his mom.
"Oh, he was staying behind today to ask the science teacher some questions on his quarterly project."
Her smile changed to a sort of grimace. "So, Rob, did you enjoy the view yesterday?"
My mind had no idea of what to say.
"Go ahead, admit it, you were spying on us, weren't you," said the inquisitor mom from next door.
Stuttering something or another, Mrs. Johnson shushed me.
"Look Rob, you aren't going to be allowed to go out with Jennifer again if you don't answer the question honestly. Were you being a little voyeur up in your room yesterday?"
We stared at each other for a minute before I answered in the affirmative.
"And you think that's a normal thing to do, spy on women from your room. What else have you looked at? Have you looked into Mr. Johnson and me in our bedroom? Have you looked up our skirts at the mall? Have you snuck in and jerked off on our panties?"
My eyes widened at the question, and I quickly said no, no nothing like that.
"Like what then?" demanded the woman.
"Nothing Mrs. Johnson, honest, I just looked out my window at you two sunbathing, I didn't mean anything by it. I mean, it was an accident and my mind started wandering and I couldn't stop looking. Please don't tell Jennifer, or my parents, Please."
She looked at me, as if to judge my sincerity. She nodded her head.
"So did you see what you wanted to see? Did you whack off at night after you looked at Jennifer? Is that where your mind was wandering?"
I didn't know what to say, but Mrs. Johnson told me to be honest or else. So I admitted that it was a great view, that I looked at Jennifer's boobs, and admitted to looking at hers as well. And I admitted I had jerked off thinking about them as well.
She should have been a prosecuting attorney. She pounced and bounced along everything I said, switching topics with her technique.
"So have you made out with my daughter, felt her up? Did you sleep with her?"
I quickly replied "NO."
Mrs. Johnson smiled a little and then nodded. "But you want to, right?"
Of course I did, what normal guy wouldn't. I explained that I would never take advantage of her daughter and would treat her with respect.
"But you would feel those breasts if she let you, right? You'd still sleep with her if you could. I mean if she said she'd give you a blow job you wouldn't turn her down, now, would you."
Damn, how do I answer those questions. Damned if I did, damned if I didn't. Luckily, my mom's car pulled into the driveway and I earned a reprieve.
"We are not done this conversation yet, buster, and you had better keep your hands to yourself when you are out with my daughter, do you understand? Do you? Otherwise there will be hell to pay."
"Yes mam."
@ @ @ @ @
It was a tough night. I had been busted by my sort of girlfriend's mom, the mother of my best friend and of course my neighbor. She had said all kinds of things that I had been dreaming about. I thought of Jennifer's boobs, and that night I pretended she was going down to me at the end of a date. Damn, my sock got filled with sticky stuff that night.
Jennifer was none the wiser that weekend. We went to a party, and on the way home she informed me that she was going out with Ryan the next night. She wanted me to know, her mother insisted I was told, so that I didn't think she was going out behind my back.
We weren't going steady, or anything, but I had to wonder if her mother had said something to her to incent her to see someone else and not the pervert next door.
Peeved, I understood the girl's decision. I did ask for a date the following weekend and she smiled, said of course, and kissed me good night, this time with a little peek of tongue.
I guess all 18-year-old guys whack off a lot. I know I did, and my friends who weren't getting laid did as well. Dan admitted he whacked off four or five times a week, just about the same as I did. I mean, we were guys you know.
The following night I watched from upstairs when Ryan brought Jennifer home, and for a first date there was more than a pack on the cheek. They kissed for a full minute and I was very jealous.
Monday afternoon I was again stopped my Mrs. Johnson on my way home from school. "So, do you want to finish our conversation?"
Reluctantly I did, admitting that I thought naughty thoughts about her daughter. "And what about me?"
I admitted it. I said I had thought of her at night, doing bad things. Being a bad girl.
"Even thought I am the same age as your mother."
I nodded yes. I said she was beautiful, that she was so very hot and sexy too. I figured if I were honest she'd be assured I wouldn't be anything but proper with her daughter.
"Okay, Rob, I trust you, and I know you won't do anything to break that trust, right? Jennifer has quite a head on her, and we want her to go to college and do well there. We don't want her head going boy-crazy. We had to break her and Ryan up the other night on the porch."
She made good points. Jennifer was the smartest girl in our class and had a scholarship to State U. That had to be important to the girl and her family.
Like before, Mrs. Johnson shocked me a little with her next question. "Are you a virgin, Rob?" After I nodded yes, she asked, "what kind of naughty things did you do to me in your nighttime fantasies? Be honest or else."
Again, it was as if I had ingested some truth serum. All came out.
"I, uh, well, I thought of you doing some bad things with me. I thought of you stripping down to your underwear for me."
"Oh you did, did you? What else?"
"Blow job. I, uh, I thought of you giving me a blow job and then bending over the kitchen counter where we had sex. There, I said it, please don't be mad at me, it was only a fantasy."
The women spoke about my active mind, and how I was very, very naughty. "I don't know, but if I thought your mother would have your dad use the belt on you I would."
We looked at each other for a bit before she smiled. "Those are naughty thoughts, but I bet Dan thinks the same way about girls. So let's forget we had this conversation and just make sure you treat my daughter well."
That night I had naughty thoughts about my best friend's mom. The following day I saw her, and she asked if I could stop by the next afternoon. "I have a couple things I want you to around the house and Dan is working on the play and Mr. Johnson is away for the rest of the week."
