Confessions of a 40 Year Old Virgin: Chapter 1

My name is Tom Sylvester; currently I’m 42 years old and single. My story started two years ago. The following is true, every last word. I’m not writing it to boast, that’s not the kind of person I am. Rather I’m writing to remind myself of the path I chose to take and how it changed the life of not only my sister, and me but also everyone involved.

Before I get to the juicy stuff let me tell you a little bit about myself. I’m not the smartest person in the world. Nor am I the most creative. I can’t sing. Nor can I dance. I’m not even that good looking. I’m kind of chubby. And I’m pretty much bald on top. I’m not what you would call a catch by any means of the imagination. However I do believe everyone has one special gift, mine is my cock. It measures 14-inches long and just shy of being 4-inches wide. At the time this story stared I would like to say my gift has pleasured women all over the world. I would like to say that, but I would be lying. The only enjoyment I’ve received from my gift has been the thousands of times I’ve pleasured myself. At this point in my life I had resigned myself to the fact that I was never going to get laid. My only source of joy was porn, which I watched a lot of, and staring at my sister’s friends.

I couldn’t talk to women. Every time I tried my anxieties about the way I looked took over, which forced me to give-up before anything got started. My therapist has often tried to say this is the fault of my parents. They couldn’t have been more wrong. My parents were amazing. I grew-up an only child in a suburb of Detroit. My dad worked for one of the big 3, my mom stayed home and took care of me. For the most part my childhood was great. Unlike some of my friends my parents actually spent time and did things with me. They made sure I was happy.

I’m going to fast forward now to several years later. It’s not as if anything interesting didn’t happen, it did. But it is not pertinent to this story. A few months after I turned 23 my parents informed me my mom was pregnant. Along with her doctors I was very worried about the effect the pregnancy would have on my mom at her age. For those of you wondering she was 45 at the time and my dad was 47. Nine months later she gave birth to Quinn Julie Sylvester. Both mother and daughter were in perfect health.

I wish I could say I was a big part of her life, but I wasn’t. Sure, I saw my family, but usually it was only once a year around the holidays. To Quinn I was more like a distant relative than a big brother. Even back then I could tell that she was the exact opposite of me. For the majority of my life I was very reserved and tended to live my life inside the lines. On the other hand Quinn was wild. She tended to live life by her rules. My dad once confided in me that him and mom wished they had Quinn first, back when they had the energy to keep up with her. I wished I could have been around more, but my life had taken me elsewhere.

Ten years later everything changed. On an icy winter night a semi went out of control crashing into the car my parents were traveling in, killing them both instantly. Which made Quinn an orphan.

At that time I was living in Chicago and was engaged to the wonderful Liza Kelly of St. Louis MO. Like me, she was also a virgin. For her it was for religious reasons. She wouldn’t even French kiss in fear that it would lead to temptation. She was very bossy toward me, but I took it, because on our wedding night I was finally going to have sex.

Our relationship fell apart before that could happen. It ended when I was granted custody of my sister. The psychologists told me that it would be best for Quinn’s mental state for her to remain in my parent’s house. Liza had no interest in moving to Detroit or becoming an instant parent to a 10-year-old. So I moved back home alone to raise the younger sister that I hardly knew.

We now fast forward to two years ago, which is six years after the death of my parents. As I said earlier in this tale this story took place when I was 40 and Quinn was 16. Back then she was still wild and still the exact opposite of me. My life was pretty boring. I had a non-descript job working in a non-descript office. Every night I’d come home talk to Quinn about her day, watch TV, masturbate and go to sleep. My sisters life was much more exciting than mine. Straight A student, cheerleader, member of the glee club and was very popular.

Over the years we’ve developed a great relationship. We grew very close. I never tried to replace mom and dad. I also did not take on the role of the over protective big brother. Instead I tried to become the cool big brother. I did not impose any strict rules. I let her make her own mistakes. She was pretty much a good kid. She did not smoke, drink or do drugs. Her only vice was sex. At 16 she was very promiscuous. At night after she thought I was sound asleep she would sneak boys (and sometimes girls) into the house to fuck. As soon as the first moan escaped her lips, I’d grab my large cock and start stroking while imagining her sucking it. I’ll admit it, I lived vicariously through her sex life since she was getting some and I wasn’t.

I’ll also admit that I was attracted to her. She was gorgeous. Everyone did a double take when she walked into a room. She was and still is considered by everyone who meets her to be an American beauty. She has sandy blonde hair, stands 5’3 and barely weighs 100lbs. She’s an A-cup. And she has an ass that draws attention of every red blooded American male that passes her—including me.

We are now at the beginning of the story. It was a Tuesday in late May 2007. I was having a terrible day. My boss had been riding me all day. I was stressed out beyond belief. On the drive home I was praying that some of Quinn’s friends were over and lying out by the pool. If they were I’d go to my bedroom, peek out the blinds that overlooked it and play with my cock while thinking about their nubile bodies. I did this a lot. I couldn’t help myself, her friends were so hot, and they weren’t afraid to flaunt that fact.

When I got home I have to admit I was disappointed. Her friends were not over. Instead Quinn was sitting on the couch, wearing tight jean shorts, a tank top and was reading a book. She briefly looked up from it and said, “Hey big brother.”

I waved.

She looked at me and said, “Bad day at the office?”

“You don’t want to hear about it,” I replied.

“You’re right,” she said laughing and went back to reading.

I walked to the fridge, grabbed a Miller High Life and joined her on the couch.

“That’s a terrible way to get rid of stress,” she said.

“Got any better solutions?” I asked.

“You could join a gym,” she said as she patted me on my gut.

“I don’t want to have a heart attack on the elliptical trainer,” I said as I removed her hand off my stomach.

“Beer is not the answer,” she said.

“For me it is,” I responded.

She looked at me for a second and said, “I have an idea.”

She then ran upstairs. I could hear her making a ruckus of some sort in her room. 20 minutes and two High Life’s’ later she ran downstairs holding a CD.

“This mix always cheers me up,” she said as she placed the disc in the CD player.

Once the music started so did her dance routine. Quinn dancing in the family room was not an uncommon site. Dance was her passion. However this was the first time she danced exclusively for me.

Her body moved in synchronicity with the beat. With every movement and gyration my cock got harder, Soon her moves got more and more suggestive. Was this intentional? Did she know what she was doing to me? By the fourth song I had my answer. She slowly took off her tank top and unhooked her bra. The nipples on her A-cup breasts were fully erect. She pinched them and smiled before turning around and sticking her ass in front of my face. Her hands moved to her front and unbuttoned her pants. They dropped to the ground. She turned back around, moved her panties forward revealing her shaved pussy and started rubbing it.

“This is how I get rid of my stress,” she said as she plopped down on the other end of the couch and started rubbing.

I couldn’t take my eyes off of her wet pussy. The mere site of her fingers playing with her clit made my cock rock hard.

“I thought you were stressed big brother,” she said in a very suggestive voice. “If you take it out you’ll feel better.”

I was in shock. Part of me wanted to whip my cock out and stroke it. The rational part of me kept on internalizing that she was my baby sister and what was happening wasn’t right. Yet I did nothing to stop her nor did I walk away. I just sat there and watched.

“I know you stroke it every night,” she said. “I can hear you when you cum, you let out a loud grunt.”

I couldn’t take it anymore. My rational side lost out to lust. I unzipped my pants and pulled out my 14-inch long, 4-inch wide cock and started stroking.

The moment she saw my cock her eyes widened and jaw dropped to the floor.

“Holy fuck,” she stuttered. “That’s the biggest cock I’ve ever seen. Can I touch it?”

Before I could say yes or no she maneuvered closer to me and placed the pussy soaked fingers of her right hand on it. As her fingers made first contact a chill ran up my spine. I looked down at her as she tried to wrap her right hand around my cock. She couldn’t. So she placed her other hand around it too and then started moving them up and down my large shaft. Her hands on my cock definitely felt better than mine.

As my eyes rolled back into my head I was still deeply conflicted. I was feeling pleasure like I’ve never felt before and I was feeling guilt like I’ve never felt before. However with every stroke the guilt got pushed back to the deepest recesses of my mind. I couldn’t believe how good this felt. I’ve been waiting for a girl to touch my cock since I entered puberty. I never imagined the first one to do it would be my little sister.

Unexpectedly she then spit on it and leaned over to put it in her mouth. Her wet lips touching my cock made me shiver. She started out by kissing the tip and then circling it with her tongue. This made me shiver once again. Then she tried to deep throat it. Instantly her gag reflex kicked in. That did not stop her from sucking me with fervor.

The faster she went, the more lost in the moment I got. I didn’t want it to end. I wanted to keep feeling this way for the rest of my life. My body had other plans. I could feel that my cock was ready to explode. I wanted to tell her to slow down, but the words couldn’t escape my mouth. I was breathing harder. Her sucking was getting faster and faster. I couldn’t take it anymore. With a loud scream of joy I unleashed a large load of cum into Quinn’s mouth.

After I blew my wad she looked up at me, smiled and said, “That was a lot of cum, when was the last time you got any?”

I sat there with an embarrassed look on my face at muttered, “Never.”

She looked at me with sadness and understanding. She stood-up and tried to give me a hug. Before she could put her arms around me the feelings of guilt flooded my mind. I quickly stood-up, pulled my pants up and left the house.

I couldn’t believe what transpired between my sister and me. I shouldn’t have let it happen. After al I was her guardian. I could only imagine how disappointed my parents were as they gazed down at us from Heaven. I also wondered how I could face Quinn again now that she knew my secret. Did she think I was pathetic?

As I sat in a diner barely picking at my food and ignoring her calls, I kept on replying the events of the early evening in my head. As ashamed as I was about them they were also amazing. And I couldn’t believe they happened with someone as beautiful as my sister. As I ate my burger, I wondered what would have happened if I didn’t leave.

I still didn’t want to face her, so I continued to ignore her calls and decided to go see a late movie so I’d return home after she normally went to bed.

A little before midnight I walked into the house. All the lights were off. As I walked up the stairs, I could hear her moaning really loud. I stood at the top listening I wondered if she was alone. I listened intently and could hear only her. The sound of her pleasuring herself was getting me rock hard. So I sat down, took my pants off and started stroking my hard cock. As I played with my penis I wondered if those moans were an invitation? I wondered what would happen if I opened her door? My imagination got the best of me. As I thought about Quinn sucking my cock again, I started stroking faster and faster and faster until I let out a large grunt as it rained cum at the top of the staircase.

“Tom is that you?” Quinn yelled from the other side of her bedroom door.

Instead of answering I ran to my room. I kept the door slightly ajar as I watched a very naked Quinn walk from her room.

“I know you were out here big brother,” she said before licking the cum off the carpet and walls.

I watched her play with her pussy as she did that. This was obviously an invitation. I wanted to be with her, but I looked back and saw the picture of my parents. I felt their disapproving eyes on me, so I wussed out by closing the door, locking it and stroking myself to sleep.

When I woke-up the next morning I decided not to get out of bed until I heard her leave. As I lied there I regretted not going for it last night. I regretted wussing out. I should point out here that even though I was a virgin and couldn’t talk to women, I did have several opportunities to get laid over the last few years. Like me these women were no prizes. They were overweight or had tons of emotional baggage. These women had given-up on life and saw me as a consolation prize. I always wanted what I couldn’t have. I wanted women who enjoyed life and lived it to the fullest. Maybe that’s why I was attracted to Quinn and her friends. Just the thinking of her got me hard.

I then heard the door slam. That was my cue to get out of bed. I got undressed and took a long hot shower. As the water splashed against my body I started stroking my cock. I vividly pictured Quinn walking into my bathroom. Shedding her clothes. Opening the shower door. Walking in. Kneeling down and giving me a blowjob as great as the one from the day before. I quickly came. Jerking off no longer felt as good. It was now a poor substitute for Quinn’s hands and mouth.

Work was torture. I couldn’t stop thinking of my sister. My raging hard cock was cramped up in my tighty whities. The pain was killing me. My boss noticed that something was wrong. Luckily he thought I was sick.

He walked over to my desk and said, “Sylvester, what is my number one rule about coming to work if you don’t feel well?”

“Don’t come in,” I replied.

“Get out of here before you get everyone else sick,” he said with authority. “Do you know what happens if everyone in the office gets sick?”

“Productivity and profits go down,” I answered.

“Now go home, feel better, so you can come back and be a productive member of the team,” he said with company pride.

By the time I got home I told myself I’d look on the Internet and find a prostitute and finally have sex. This was something I never wanted to do. Don’t get me wrong, I’m not opposed to paying for sex, I’m more worried about getting busted like my friend Dave. He was arrested for soliciting 5 years back. His picture was in the news. His car was impounded. His wife left him. He lost his job. He lost everything. Last I heard he was living with his mom working as an assistant manager at Pizza Hut.

I couldn’t do that to Quinn, nor could I afford to lose my job and take a gig at Pizza Hut. As much as I wanted to lose my virginity I decided to settle for second best by jerking off to porn in my room until baby sis gets home.

I walked to my room trying to decide which porn to watch. I was lost in thought and did not hear the moans at first. I thought it was my imagination playing tricks on me, so I did a double take and saw a naked Quinn rubbing her pussy on my bed.

Our eyes met as she said, “I can’t stop thinking about your gigantic cock big brother.” Maybe it was the way she said big brother or that she was masturbating on my bed. I closed my eyes and said, “Forgive me.”

I then walked over to the picture of our parents and turned it away from my bed. I turned around and watched Quinn lustfully staring at me as rubbed her clit. She never looked prettier then she did at this moment. I moved to the foot of the bed, kneeled on the floor, moved her closer to me, stuck my head between her and my tongue in her pussy.

The second it made contact she squealed, “It feels so good big brother.”

I didn’t know what pussy would taste like, or if I would enjoy it. Within seconds I realized it tasted great and that I loved licking it. I looked at Quinn, she was moaning and pinching her nipples as my tongue explored her. By the sound of her moans I knew I was doing something right.

“Keep sucking my clit the way you’re doing it,” she screamed. “I’m going to cum all over your mouth.

I kept on doing as I was told until I heard her scream, “I’m cumming.” She then looked at me and said, “I see you were paying attention to all your porno’s. Now come closer to me and let me taste my cum on your lips.

As I moved closer to her I wondered how she knew about my porn collection. I also wondered if she’s been in my room, watching them alone or with her friends. Just thinking about that got me even more excited.

I was now next to her. Her face moved closer to mine. Eventually our lips touched. We kissed like lovers instead of siblings. Our tongues danced in each other’s mouths. I never felt more alive.

She soon had me kneeling on the bed. She took off my shirt. Moved her mouth from my lips to my nipples. She then slapped my belly and kissed it. Finally she got to my pants. She slowly unbuckled them. Then unbuttoned them. Then unzipped them. Then she let them drop. She started to lick the outline of my cock on my tighty whities then moved her way to the top of it, which was sticking out of my underwear up against my belly.

“I’m going to set your cock free big brother,” she said seductively as she pulled my underwear down.

My cock was sticking straight out. Her hands wrapped around it and she started stroking it. She then leaned in and spit on it.

Before putting it in her mouth she looked up at me and said, “You have a beautiful cock.”

She then started licking my love missile. I got excited watching my cock fill her mouth. Watching her tongue circle the tip as her right hand stroked it. She then moved my cock up, licked underneath it, moved down to my balls and up again, before putting it back into her mouth. I was in ecstasy.

A few minutes later she looked up at me and said, “Are you ready to fuck me?”

“Yes,” I responded.

I had her lay on her back. I licked her pussy for a few minutes while she begged me to fuck her. How could I say no to her? So I stood-up, spread her legs and moved her to the foot of the bed. I slapped my cock on her clit. She squealed and screamed, “Stop teasing me and start fucking me.”

I started to slide my cock into her warm, wet pussy. I moved it in slowly. I looked at her face and body as I did that. As my large cock started to enter her, she bit her lip and it looked like she was in pain.

“Am I hurting you?’ I asked as I slid my cock all the way in.

“No, you feel really good” she said with a smile. “Big brother, you’re no longer a virgin.”

I leaned down and kissed her as my cock moved in and out of her pussy. This was the moment I’ve been waiting for since I started jerking off many years ago. And it felt better then I even imagined. With every thrust I prayed that I’d be able to last so I could try every position.

She then started rubbing her clit and said, “Fuck me harder.”

I started moving faster. Her body started quivering. She increased the pace of rubbing her clit. Her body started shaking as she yelled, “I’m cumming.”

Instead of decreasing my thrusts I sped up giving her another orgasm minutes later.

“Let me taste my cum on your cock,” she demanded.

I got on my knees on the bed and let Quinn put my penis in her mouth.

After I thought she had enough I had her get on all fours. I slapped her ass before resuming fucking her.

“Slap it again,” she demanded.

I slapped it.

“Again,” she screamed.

Once again I did as I was told.

Between every thrust I slapped my sisters beautiful ass.

“Go faster,” she screamed.

This time I did not do as I was told. If I did that I knew I’d cum in minutes. Instead I slowed my movement to a snails pace.

“Why are you teasing me?” she asked. “Please go faster.”

I didn’t. I moved my hand under her and started rubbing her clit. This seemed to appease her a few minutes. I didn’t realize how tiring doggy style would be; as much as I enjoyed fucking her from behind I could feel my knees getting weak. So I asked, “Do you want to sit on my cock?”

“Oh yes,” she responded.

I laid on my back while Quinn sucked my cock. Minutes later she climbed on top. I watched as my massive member stretched her pussy. I once again started slapping her ass as she started riding my shaft. My fingers soon found their way to her asshole. I started playing with it. She really enjoyed that. It made her ride me faster. Which caused me to move at a more rapid pace.

“That’s the way I like it big brother, hard and fast,” she said. “So go faster.”

I moved faster than I ever thought I could move. All I could think of was giving my sister another orgasm. I kept on fingering as the speed of my thrusts increased. She started moaning louder until she screamed, “I’m cumming.” She then collapsed on top of me as I continued to fuck her at a frantic pace.

She kept on moaning as I moved in and out of her. My cock was reaching its breaking point. I didn’t want this moment to end. I kept on thrusting until I knew I was about to cum. So I lifted Quinn up and shot my load all over the place. Some of it landed on her, some on the bed and a lot of it on me.

“You could have cum inside me,” she said, as she tasted my joy juice.

“Next time,” I said.

“What makes you think there’s going to be a next time?” she said laughing.

“Was I bad?” I asked.

“You were great big brother,” she said before leaning down and kissing me.

I held her in my arms as we made out. She broke away for a minute and said, “I can’t wait to share you and your cock with my friends.”

As I held her in my arms I knew the best was yet to come. And I couldn’t wait.