Virginity Has Its Perks Ch. 01

This is a work of fiction.

Sometimes I wonder if life gets easier. My Mom, Jeanne, used to tell me that "Every experience is just a part of growing up Bobby". Well if it was then it was literally hell growing up. At least for me it was (computers, debate team, etc, you get the idea, half nerd, half normal guy, still an outcast), my sister Holly on the other hand seemed to have it easy. She graduated 2 years ago and got a scholarship to one of the local community colleges (she still stays at home in her old room to save money).

So here I am sitting in my room staring at my computer screen wondering just what the hell was I going to do tonight. It's been exactly one week since I had graduated high school and so far all I had managed to do for this summer so far was sit in my room and play games and watch TV.

The big plan was to start searching for a summer job and make a little money before classes started next fall for community college. I would do the same as sis and stay at home for my first 2 years then if I got accepted to a 4 year school would see what my options were. It's not that I didn't have friends, I did, I was just depressed for another reason. I am still a virgin. Yup, while some guys get laid early on in life I was one of the lesser' on the social scale. I'm one of the nervous fidgety types that get tongue tied and feel my stomach tie up in knots when it comes to asking women out on a date. I've reasoned it out a thousand times and I still can't seem to get a grip on things when it comes to women. And for that reason I am a virgin.

It's not that I can't talk to women; I can, just when it comes to the asking out part my fear of rejection overrides my hormones. And I know I'm not a bad looking guy, I started lifting weights every day this past year and do cardio at the gym every other day, sometimes the bike, sometimes the treadmill, I keep myself in shape. At 5'10", 180 lbs with brown hair and blue eyes I'd say I look pretty good for an 18 year old. My mom tells me I got my dad's good looks and that's about the only thing of his I take after.

Oh well, I still got internet porn and hand lotion, someday I'll get over my fear, just takes time I guess.

Glancing at the clock on the bedside table it was 4 pm, mom should be home soon and my sister Holly wouldn't be too long behind her. Guess jerking off will have to wait till later tonight. Might as well head downstairs and see whats on TV.

Flipping through the channels sitting there in my sweat pants and t-shirt I hear a car pull up in the driveway and into the garage. After a couple minutes I hear a key in the lock and my mom opens the door and walks in.

Now some people just look at their mother as their mother, they never really notice how attractive or unattractive they are. My mother Jeanne was attractive; I first noticed how she looked when I hit puberty. At 5'6" she couldn't have been more than 115 lbs, with the stylish short brunette hair and blue eyes she had a stare that could pin you to the wall (I know, when I got in trouble in my younger days she always used it). And she had the most perfect set of big tits I had ever seen on a woman, I don't know the size, but if I were to guess I would have to say in 36+DD range. Overall she was a knockout, even if she didn't like to flaunt it very often.

Mom was a very successful real estate agent; she could sell almost anything if it was planted into the ground. Right before I was born our dad had run out on us, mom said he had given the excuse he just couldn't be a family man and left one night. Mom said she had never heard from him again, good riddance I thought. After I was born mom had already finished high school so she decided to get a job as a secretary to one of the real estate firms in the nearby city. She worked there for 3 years learning all about the business and finally became a real estate agent herself. She opened her own agency after 5 years of being in the business and now after only 10 years she had a well earned reputation and a very comfortable living for herself and us.

Today she had on the light blue silk blouse with navy blue skirt, with high heels. A conservative look to be sure but it still didn't hide the fact she had something up top that made men drool after her.

Noticing me on the couch "Hi Honey, how was your day?" she says while leaning to kiss me on the forehead.

"Just another day" I replied sighing. Hoping she would leave it at that I start flipping through the channels again.

Of course, she didn't.

"Bobby whats wrong?" she asks while sitting next to me and looking at me with that concerned mother look.

"Mom its nothing, it's just guy stuff, don't worry about it" I replied.

"Guy stuff huh? Is it about girls?" she asked.

With my face reddening a bit I keep my mouth shut hoping she'll take the hint and not embarrass me any further.

"Honey talk to me please?" she says while stroking my hair like she used to when I was little.

Why can't I ever just keep my mouth shut or tell a really good lie every now and then I wonder.

"Yes if you must know it's about girls." I said flipping through the channels.

She looked at me for a few seconds then took the remote out of my hand and turned off the TV.

"Look at me Bobby." She said.

It was the same voice she used when she wanted my attention and it was damned hard to ignore, so I didn't. I turned and looked at her and she just smiled still stroking my hair and asked me "Now whats the problem sweetie?"

For some strange reason my mom sitting there looking at me so concerned and understanding like and smoothing my hair back had a type of hypnotic effect on me.

And all at once I just blurted out "Mom I'm a virgin!"

Now with my face as red as some of the wine she had in the fridge I buried my face in my hands and just sat there. Her hand had stopped and moved to my shoulder, I felt her give me a gentle squeeze.

"Honey look at me." She said.

I looked up and she was still smiling.

"It happens for everyone at some point in their life, for some it takes longer than others, it's nothing to get upset about." She said soothingly.

"Yea I guess." I reply looking back at the TV.

"Have you been on any dates lately?" She asked.

I guess one thing I should come clean about. Every now and then just to keep up an illusion of a normal teenage boy I would on occasion borrow the car on a Friday or Saturday and go out of town on the pretense of having a date. I get the suspicion my sister knew I wasn't going on a date, but I'm pretty sure I fooled my mom into believing it. And now I'm pretty much fucked I thought.

Sighing to myself I decided to tell mom the truth.

"Mom I've never been on a date before" I said still looking at a blank TV screen.

I glance over at my mother and see the shocked look on her face, just sitting there looking at me in disbelief.

"It's true, all those times you loaned me the car I drove over to the mall or across town to the movies or the bookstores and just hung out there, sometimes with friends and sometimes by myself." I said. Glad to finally get it off my chest.

"Honey why haven't you told me of this before?" The concerned mother was back again.

"Look mom it's not that I don't want to date, I just can't. When I try to get up the nerve to ask a girl out my insides knot up and I can't think straight. I'm so afraid I'll be rejected that I just can't do it." I say looking up at her.

Just then we hear my sister's car pull up in the garage.

Patting my leg mom gets up and moves to the hallway, just before she leaves the room she turns back to me.

"We're going to talk about this later Bobby, ok?"

"Ok Mom."

Saying that she turned and went upstairs. Hearing her bedroom door shut I turn back to the TV and turn it on to see if I could find something to watch.

Less than a minute later my sister walks in the door carrying a couple bags from one of the local bookstores.

Now my sister Holly isn't a mirror image of her mother, she is about the same height and has close to the same cup size of mom (somewhat smaller, but not by much) and that's where the comparison ends. Where mom's hair is dark, Holly is a natural red head, with freckles to match. Mom's hair is cut short and Holly's is below shoulder length. When she has it in a braid it looks like a trail of fire swaying down her back. Today she had it in a simple pony-tail and wearing jeans and a white t-shirt.

"Hey lil bro wanna help me out here?"

"What for? Looks like you got it handled." I said grinning.

"Bah, I still got some stuff in the car I gotta bring in, my pack and a couple of charts I've been working on for a project, will you run out and grab them for me?" She said practically begging.

Sighing I turn off the TV, nothing good on anyway.

"Ok but you owe me."

In response she stuck her tongue out at me.

Going to the door I moved around her as she was headed for the stairs and noticed her jeans had slipped a bit on the backside. I saw a sight that caused me to stop dead in my tracks; she was wearing a black silk g-string. That in itself would mean little, but with the faded jeans slipped down as they were and her tanned skin it made it impossible for me not to stare. And apparently my cock had the same idea; it started rising up to see what the fuss was about. Watching her ass sway back and forth while she crossed the room with that thin piece of silk swishing ever so delicately across her skin was hypnotic to say the least.

"Enjoying the view?" I heard a voice ask.

Startled I looked up and saw my sister looking over her shoulder at me from the bottom of the stairs with a wicked little grin on her face. Knowing I had been caught all the blood left my cock and went straight to my face and I made a hasty exit out the front door.

Opening the door to her blue compact I reached inside and grabbed her back pack and a couple of long rolled up charts she wanted and pulled them out.

Breathing heavily I decided to stay outside a few minutes and let myself calm down before going back in. After a couple minutes I looked into the driver's side mirror and saw that now there was a reasonably normal color to my face I went back inside lugging my sister's stuff.

When I came back inside my sister must have gone on upstairs so I unceremoniously dumped all her stuff at the foot of the stairs and went back in the living room to try to watch TV this time.

A few minutes later I heard my mom calling for me so I turned off the set and went upstairs to her room.

Knocking on her door I heard her voice say come in and I opened the door and went inside. My sister was sitting there on the edge of the bed still in her jeans and t-shirt. She smiled when she saw me and winked.

I decided to ignore her and looked to mom. Mom had changed into an old t-shirt and a pair of tan colored shorts. She asked me to run pick up some of her suits from the dry cleaners across town and to stop at the Chinese place on the way back, as she didn't feel like cooking tonight.

"Sure mom. Need anything else?"

"Nah sweetie that's all." She said smiling. She gave me the keys and as I was about to leave I noticed my sister still grinning and she suddenly giggled. I turned to look at her and then I noticed mom now grinning at me, confused I shrug my shoulders and left the room, leaving the door open.

The trip across town took more than an hour, mainly because of the afternoon rush of people wanting to get home. But other than that it was uneventful, I got the dry-cleaning mom wanted then on the way back stopped by the Chinese place for takeout. With the food and suits now in the car I headed for home. More than halfway back I had to turn on the headlights, it was getting dark. It was close to 6 pm by the time I pulled into the driveway and pulled into the garage.

I unloaded the car and brought the takeout and set it on the kitchen table then took mom's dry-cleaning upstairs to her bedroom. I heard the shower on and figured she must have just jumped in so I opened the door and walked in.

What I saw stopped me dead in my tracks. There was mom with her back to me, looking through her closet with not a stitch of clothing on. Her ass was nothing short of perfect, very light tan and perky as they come, and her legs, they looked as smooth as silk, just in that glimpse my cock shot up to half-mast in a split second.

Time seemed to stop for just a few seconds, or maybe it was my lust addled brain that made it seem that way. But all too quickly time started again and my mother must have sensed me in the room or felt some cool air rush in from the door opening, because she looked over her shoulder and just winked at me.

She then looked back to the closet and calmly pulled a cream colored robe out and put it on with her back still to me, then turned to face me as she was tying the sash.

"Well?" Mom asked

Suddenly realizing just what I was doing, I looked up at her face and saw her grinning and for some reason I felt embarrassed, but not mortified like I should. Instead of hauling ass out of there I just grinned sheepishly and lay her dry-cleaning down on the bed and made a retreat out the door without looking in her direction again. Just as I was about to shut the door mom told me to wait a sec.

"Honey?" she said, trying to get my attention.

She had to have had her robe on by now I reasoned. So I cracked the door and stuck my head in.

She was brushing some lint off her robe or something when I stuck my head back in.

"Whats up mom?" I asked

"Take this and throw it in the laundry room for me sweetie."

I opened the door a little further and stepped halfway into the room and looked around, I didn't any clothes anywhere except for the dry-cleaning I had just brought in.

Then I noticed she was undoing the sash at her waist and then slowly, while looking me straight in the eye, she opened it and shrugged her shoulders. It fell into a pool at her feet. I was stunned, I started breathing hard and my cock started rising of its own and this time I took no notice of it. I just couldn't take my eyes off of her, she was drop dead gorgeous. I looked her up and down, from the tops of her big tits with huge nipples down to her perfectly shaved pussy lips, I was mesmerized by her beauty.

Then I was suddenly jolted back to reality when she reached down and handed me the robe, still grinning she shooed me out the door as if she wasn't standing there naked and shut it behind me.

I stood there for a moment to get my breathing under control and looked down. To my horror my cock was standing at fullmast. Mom had to have seen that I thought. I was never one to brag but I did have a nice tool, a little over 8 inches would be a good estimate.

Ok calm down Bobby, even if she did see it think for a minute, I thought. She wanted me to see her, that's why she pulled her robe off, to get this kind of reaction from me. But why would she do that? I argued with myself for a minute or so before my cock had finally deflated enough to be hidden in my sweats again.

Composing myself I went downstairs to the laundry room and tossed her robe over in the hamper by the wall, then went back into the kitchen to get out some of the food that I had brought home. Holly came down a few minutes later just as I was setting into some honey chicken. She had changed into a pair of running shorts and a blue wife beater. Coming up to the table she took out a few things and made herself a plate.

For some reason after she sat down she stared at me, as if she wanted me to make conversation with her. After I was almost finished eating I finally took the bait.

"What?" I asked.

"Hmm?" she replied smiling around a mouthful of beef teriyaki.

"What's with the staring and grinning?"

"Why I don't know you mean Bobby" she said playing innocent.

"Fine be ignorant then." I said finishing the last of my food in annoyance.

She just kept smiling as I got up and rinsed my plate off and set it in the drain to dry.

Just then as I was about to leave the kitchen my mother walked in, she had on this light cream colored kimono style robe, and was still drying her hair with a towel.

"Smells good" She said as she went to get a plate from the cabinet.

Seeing no reason to hang around in there I decided to head up to my room to play some games a bit and maybe get a chance to take care of my frustration. Just as I was about to leave Mom called to me.

"What's up mom?" I asked turning around.

"We need to talk sweetie about your problem, it might as well be now."

"Holly is here Mom ..."

"Yes I told her about it."

"Mom!" I said I couldn't believe my ears, she had told Holly?!?!

"It's ok Bobby, it's no big deal, and mom told me so she could get some advice since I had been dating more recently than she has." Holly said with a small smile. For some reason Holly's smile wasn't one of the smirks I was accustomed to, this time she actually seemed like she wasn't teasing, women are strange I thought.

Mom was speaking again, it took me a moment to get over my shock and hear what she was saying.

"Bobby you have to get over this fear you have, you can't have a normal life until you do."

The concerned mother was back and this time Holly took on the same look as well.

I went back in and sat back down, not saying anything just staring at the table.

After taking a couple bites of her food Mom got up and got a bottle of wine out of the fridge and opened it and told Holly to get 3 glasses out of the cabinet.

"I think we all need to relax a bit if we're going to talk about this Bobby." She said.

After pouring us all some wine Holly sat back down and sipped hers as did mom, but as for me I rarely get the chance to drink so I downed mine in 2 gulps, mainly from all the embarrassment I had had today.

"Slow down Bobby, you need to relax sweetie, not get drunk." Mom said, while pouring more into my glass.

"Sip it sweetie" she said setting the bottle back down.

So I did, and then the inquisition started. Mom and Holly both wanted details as to what exactly happens when I try to talk girls, and as best I could I explained. They wanted to know what I had been doing to try to get over this fear and all the ways it sets it off, etc.

This went on for a little while, and somewhere during the conversation we finished off the first bottle and started on a second one.

During a lull in the conversation Mom glanced at the clock and saw it was well past 9 pm, and said we should continue in the living room where we would be more comfortable. Grabbing a third bottle out of the fridge we all went into the living room where mom and Holly sat on the couch and I sat on the love seat. But mom wasn't having it, she told me to get in between her and Holly on the couch so we could talk. Holly just giggled; she was pretty lit by now.

As for myself I was halfway to being drunk myself and didn't think anything of doing what my mother told me so I moved over to the couch and sat in between them.

"Alright, we've discussed all the ways you've tried to get over this and all the ways you haven't, but I think it's time to try something new." Mom said with a wicked little grin.

Holly knowing that to be her cue stood up and pulled her wife beater over her head. Her tits sprang out into the open air and bounced a bit before settling back down, she casually tossed the shirt to the side and grinned at me.

I just stared with my mouth open like an idiot, not talking or even blinking, they were just gorgeous. Her tits were almost as big as mom's with big nipples to match. My cock instantly rose up to full mast and was pushing at the waistband of my shorts. Holly sat down on the loveseat and crossed her legs and just leaned back into the cushions, looking as if it were the most natural thing in the world to sit there with her top off in front of her mother and brother.