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I Train My Own Personal Boy Toy Ch. 1
How It All Began
Welcome everybody! My name is Samantha and I live in a teeny tiny town in the Midwest. My two best friends in the world are my neighbors, Holly and Haley. We have been joined at the hip for as long as I can remember because we grew up living exactly the same lives. My father and their father went to high school and college together, married their sweethearts and began their family lives living right next door to each other. Our mothers are both nurses at the University Hospital, which is about a 40 minute drive. Our fathers had degrees in finance and got jobs out of college working for competing institutions in the city, commuting together for the hour long drive every day.
As the story goes, our fathers were spending the weekend grilling and having a few beers when they came up with the idea of partnering in their own wealth management and investment company. They became very successful over the course of four or five years and added six full time associates, occupying an entire floor of the tallest building in the city.
Holly, Haley and I were born within a couple of months of each other. Unfortunately, with our parents commuting to different cities daily, their marriages suffered, eventually leading to separation and divorce when the twins and I were in middle school. All of them remain great friends to this day, they just wanted different things for their lives.
Both of our fathers moved to the city to run their business. Our mothers decided they didn't want us to grow up in the city and decided to stay in the dinky town until we graduated high school. It was taxing on them to have to drive a long distance to work, often working double shifts, but they did it for us. They would have to arrange a babysitter for us when they worked the same shift, so the twins and I were always together. Once we reached high school, we were allowed to stay on our own. Our fathers made lots of money and took good care of us girls and our mothers. We even found out that there was a large trust account set up for us that would become ours when we turned 21. In the meantime, our fathers were always giving us spending money, which we each put away in the bank so that we now have a nice little stash to do whatever we want.
Now let me tell you a little bit about my hometown. It is so small that we attended high school in one of those consolidated school districts with three other tiny communities. For whatever reason, there were way more girls in the school than boys. Maybe it was something in the water. The ratio was just short of two girls for every boy. Now if you were a boy, that was great. But it sucked for us girls. We were left to squabble over the boys. Even the guys most would find undesirable had no problem getting a girlfriend.
Holly, Haley and I were the academic types throughout our first three years in high school. We didn't spend much time doing our hair, primping or keeping up with all of the fashion trends. As a result, none of us had a boyfriend. There wasn't anything else to do in this town, so we focused on school work. It paid off. The three of us were always the top students in the district. Scholarship offers began coming in and we started talking about attending the major university that was about a 40 minute drive away.
By the time our senior year started, our lack of social lives became a point of frustration. I even overheard a couple of boys in the school cafeteria saying how they thought we could be cute if we just made a little effort. That hit hard. We had been telling ourselves for a couple of years that it was just a numbers game. Now the truth was apparent.
One day after school, we were watching tv at my house and I told Holly and Haley what I had heard the boys saying about us. Our initial anger turned to sadness, realizing we may have wasted more than three years of high school because we hadn't "made a little effort." We didn't want to get to college and be outcasts there too, so we decided to make some changes. It was time to use some of that saved money. There was about four months left until graduation and we wanted to make them count.
The following weekend, I drove the twins to the capitol city on their 18th birthday to get our hair and makeup done and to shop for new clothes. The first stop was the salon for hair and makeup. The twins were identical and most people had a hard time telling them apart. They each had long blond hair to the mid back level. Holly wanted to keep her hair long and opted for a braided pony tail that hung down her back. Haley got a pony tail too, but cut her hair shorter so that it bounced around the back of her head.
Unlike the twins, my hair is brunette. Not really dark, but not light brown either. I elected to just get a cut and add some waves and a few highlights. Holly's hair was longer than mine and Haley's was shorter. This was a good start.
Next we got makeup. The stylists were great, taking the time to show us how to do the makeup ourselves and how to do our own hair at home. They gave us some tips for changing up hairstyles to mix things up a bit. When all three of us were finished, we gushed over how much of a change it had made and how beautiful we were. I really wish we had done this sooner.
The make-overs at the salon took longer than we had anticipated, so it was late in the afternoon. We decided the clothes would have to wait for another day. We drove home and found lots of cars around our houses. Family and friends had gathered to celebrate the twins' birthday. Everyone showered us with compliments on our new looks. We knew we were onto something.
The following week at school, the guys took notice. We were turning heads now. The girls ignored us and sneered at their boyfriends for looking at us. It was great! We were making them jealous and our transformation wasn't even complete yet.
Unfortunately, several weeks passed before we had an opportunity to go back to the city for new clothes. This time, it was my 18th birthday. Holly drove us and we spent the entire day buying skirts, shorts, jeans, tops, shoes and anything else we could find to spice us up. It was the most fun I had ever had. The car was full of shopping bags and our smiles were wide. Just as we were ready to head home, a thought occurred to me.
"We're not done yet," I said.
"What do you mean? Where else do you want to go?" Haley asked.
"Sexy lingerie!" I said.
Holly and Haley burst out laughing. I just looked back with a straight face.
"Seriously?" Holly asked.
"Yeah, why not?"
"Who's going to see them anyway?" Haley asked from the back seat.
"You never know," I said, turning in my seat to look back at her. "If you hooked up with a guy right now, would you want him to see the panties you're wearing?"
"What's wrong with what I'm wearing?"
"Well, let's see," I challenged.
"You're crazy," she giggled, trying to ignore me.
"No c'mon. Let's see your underwear. I'm serious."
Holly was watching in the mirror as Haley defiantly unsnapped and unzipped her jeans, revealing the top of her white panties.
"Pull those jeans down, so I can see what they are."
Haley lifted her butt slightly and wriggled the jeans down to mid thigh.
"They're granny panties!" I exclaimed.
Holly laughed as Haley blushed and quickly pulled her jeans back up.
I looked over to Holly, "I suppose yours are the same?"
She didn't answer, just giggled and nodded embarrassingly.
"Are you guys in?"
They both smiled in agreement, so we headed back to the mall. At the entrance, we nervously looked at each other before timidly walking in. None of us had ever bought anything like this before. Once we got to looking around, we were like kids in a candy store. Silky panties, cute cotton panties, thongs, bras, camisoles and nighties! Each of us had an armful of sexy undies for the cashier to ring up. On the drive home, we made a plan to meet up at the twins' house on Monday after school to put outfits together and try on our new lingerie.
The school day seemed to crawl and I had a hard time controlling my excitement. It was getting close to the end of the year and graduation, but I was thinking about looking sexy and attracting guys. Our grades were mostly set and we all had scholarship offers, so it was time to live it up a little.
When the day was finally over, Holly drove us to their house and I dashed next door to retrieve all of my purchases. We only had a few hours before our mothers would be home, so we piled all of the clothes on Haley's bed. None of us knew what to do from there and just looked at each other.
"What do you want to do?" Haley asked.
"Well, let's try on the underwear first," I said.
"You try yours first," Holly said nervously.
It was weird. We had known each other since we were old enough to talk, but I couldn't think of a time when I had seen either of them naked. It can't be that big of deal I thought to myself. And it was only fair for me to go first I guess since I had initiated all of this. But it was hard to get started with the two of them just looking at me.
"Why don't we do it together?" I suggested.
Holly and Haley looked at each other, then back to me. I took a deep breath and pulled my t-shirt over my head. I paused to watch them, then unbuttoned my jeans and shimmied them down, now standing in front of them in my plain white bra and gray cotton panties. My face blushed because my delicates were utterly boring. Haley reached for the button of her jeans and Holly followed suit. In a few seconds, they were down to bra and panties. I gave them a "you poor thing" look because they both had plain white bras with those cotton granny panties. None of us moved for about two full minutes, waiting to see who was going to be the first one brave enough to show some real skin.
Haley gave a wicked look to Holly and in a second, they were on me. Holly went behind me and unhooked my bra and Haley snatched it away, tossing it on the bed. Before I could even protest, Haley hooked her forefingers in the waistband of my panties and quickly yanked them down. I felt like one of those store mannequins that was being changed.
I needed to get the attention away from my embarrassment, so I reached over to Holly, pulled the straps of her bra off her shoulders and spun it around so that I could unclasp it. It came off easily and I stuck the four fingers of my right hand inside the front of her panties and yanked them to the floor. Now Haley as the only one that wasn't naked. That didn't last long. Holly took the bra and I snatched the panties off her.
There we stood, shyly giggling as we tentatively looked over each other's bodies. All of us were about 5'6" with thin builds. I was 125 pounds and guessed they were about 120 each. I had slightly larger boobs, a medium b-cup to their small b-cups. Much like their faces, their bodies were nearly identical. The nipples were puffy and pink around the edges and gradually faded to creamy white at the tip. My nipples are darker with pencil eraser nubs that are almost always erect. I do have to say that we have three very nice sets of tits! Nobody ever would have known this because of the baggy sweatshirts we tended to wear.
Once we had a good look at each others tits, our gazes moved downward. Hmm, not as appealing as I had imagined. None of us shaved our pubic areas and it was all a bit overgrown. Their hair was light brown, wispy and spread all the way to their leg creases. Even though it was light in color, it stood out sharply against their pale white skin. I had no room to talk. My hair was black, bushy sand stood out like a beacon against my skin.
"Um, do you think we should do something about this?" I said circling my finger in front of their crotches.
"Like what?" Holly asked.
"I think the in thing is to shave it," I answered.
"Are you sure?" Haley asked.
"Go get your laptop. We'll look it up," I suggested.
Haley retrieved her laptop and we searched for pubic hair, which led to razor ads and creams. So I typed, "what do women do with pussy hair?" Holly and Haley gasped and laughed at my wording. Then, the screen lit up with porn sites. I clicked on one of the video thumbnails and it began to play. The room was dead silent as we watched a guy walk up behind a woman preparing food in the kitchen. In the span of about one minute, he had her stripped naked and lifted her onto the counter top.
"H... hey, I don't want my laptop to get a virus," Haley said.
"Don't worry about it," I said intently watching the video to get a look at the woman's pussy.
The guy in the video spread her legs and there it was! Not a hair to be found.
"Go back and see if you can find any with girls our age. That woman looks older. Maybe younger girls don't shave it all off," Haley said, apparently having forgot all about the risk of virus.
I hit the back button to the screen with hundreds of little thumbnails. I scrolled down, eventually coming across a picture of what looked to be teenaged girls on a boat. It turned out to be a spring break video that began innocently enough with several bikini clad girls drinking and partying. I fast forwarded to the point where the swimsuits began to come off. We watched with great anticipation as one of the girls stepped between the legs of another girl and pulled her bottoms down. Shaved bare. Fast forward some more to where all of the girls were naked. I counted five completely shaved and two with some pubic hair.
I stopped the video and the three of us looked at each other, inevitably lowering our gaze to our hairy crotches.
"Um, we need to do something about this," I said pointing to my bush.
"You want to shave it off?" Holly asked.
"I'm not sure. Maybe I'll trim it and see how it looks first. Then I'll let you know."
"Why don't you do it right now?" Haley asked.
"HALEY!" Holly screeched.
She didn't respond, just looked at me expectantly. "Well?"
"You want me to shave my pussy in front of you?"
"Or we'll do it for you."
The temperature in the room went up drastically. None of us had any sexual experience and I was getting excited. Scared and excited. Haley's eyes were almost begging me to agree. Holly sat there dumbfounded. I was unable to form any sort of reply. Then Haley scrambled off the bed and scurried out of the room, returning seconds later with a towel, razor and shaving cream.
"So how bout it? You want to?" She asked.
I still couldn't answer. My hand was subconsciously covering my pussy. Haley decided to just go for it and spread the towel out next to me on the bed.
"Slide over here," she said, patting the towel.
I didn't move right away, so she grabbed the inside of my knee and started pulling my leg. This was exposing my pussy more, so I obliged and settled on the towel. What Haley did next truly shocked me. She knelt down beside the bed, pushed my knees apart and moved in between. I was thoroughly embarrassed, but her body blocked me from closing my legs. Next, she grabbed my calves, raised my legs and put them on her shoulders. I was forced to lay back, completely spread open to her and her sister. I could actually feel my pussy lips spreading open!
"Ooh, we're wet already," Haley remarked, deepening my embarrassment.
She handed the shaving lotion to Holly and said, "here, spread this on."
Holly tentatively took the can of gel, held it over my bush and sprayed a few dollops on me.
"Well, lather her up," Haley directed.
Holly was hesitant to touch another girl's pussy but eventually reached over my leg down to my crotch and began to smear the cream around. I had to stifle a loud moan. It was the first time any fingers had touched my pussy that didn't belong to me. I absentmindedly toyed my nipples as Holly's fingers twirled in my pubic hair. All too soon, she had finished her assignment and Haley picked up the razor.
She started with my thighs slowly cleaning off the areas adjacent to my crotch. With that finished, she pushed my legs off her shoulders, planting my feet on the bed. I felt the razor glide over the top of my bush a couple of times before Haley backed away.
"This isn't working. It keeps getting clogged up. Don't move," she said, scrambling out of the room again.
I felt like an idiot laying there naked with my legs spread and Holly staring at me. But in a flash, Haley was back with a tiny pair of scissors. She knelt in front of me again and pulled my hair up, snipping it off in clumps.
"Hey, don't cut it all off right away. I'm not sure I want to be bald down there yet," I complained.
"OK, we'll just trim it for now and see how it looks."
She continued clipping while Holly looked on. Once she had it cut short, she pushed my knees wider apart, began cleaning up the edges and shaping what was left. She then pulled the towel from under me and wiped all of the remaining water, cream and hairs away.
"Whoa! That is hot, dude," she said.
"Let me see, let me see," Holly said excitedly as she leaned around Haley. "Ooh, sexy!"
"HOLLY... HALEY!" a female voice called from downstairs.
"Shit, mom's home," Holly said as she scrambled around in a panic to find some clothes.
"WE'LL BE DOWN IN A MINUTE," Haley hollered back.
We all dressed and composed ourselves as quickly as possible and went downstairs. I didn't see their mom, so I slipped out the door and went home. Of course my mom was home now too since they drove to work together. We made small talk for a few minutes, but all I could think about was my pussy. I wanted to go look at it.
Mom said she wasn't hungry, but would make me a sandwich if I wanted. I told her I would eat something later as I had some school work to do and rushed upstairs to my bedroom and closed the door. In five seconds I was naked, standing in front of my full length mirror. Damn, it WAS sexy! I went into the bathroom and got the handheld mirror to look at it from every angle. Moisture was glistening in the light. Suddenly I had an urge to go back to the nudie sites on the computer. I decided to use my desktop because it had a bigger screen.
I sat down naked in the chair and started the computer. Waiting impatiently for it to start up, I rolled over in the chair and locked the door, then scooted back to the now live computer. My entire body tingled with excitement typing in keywords: naked, nude, sex, and porn. This was the first time in my life that I had any interest in anything like this.
It took a few minutes to get the hang of the sites and avoid links that took me off somewhere else, but I eventually figured it out. The girls were all so beautiful with well manicured crotches. I felt ashamed of myself for not paying any attention to mine. Oh well, nobody was the wiser, except Holly and Haley, and they were just as bad as me.
Then, I started focusing on the guys. I had never really seen a penis before. At least not on a real man. There were drawings and illustrations from sex ed books, but this was the real thing. I watched dozens of videos over the next half hour, marveling at how they would go from small, floppy tubes to big, hard poles. Some were circumcised and some weren't. I have to admit, the un-circumcised ones were less appealing to me. The circumcised ones were less wrinkly and just looked better to me. Their balls were interesting too. Some were dangling low and some were nice and tight. One guy even seemed to have his move around inside the sack without even touching them.
In one video, the guy pushed the girl down on the bed, peeled her panties off and began running his thumb up and down through the folds of her pussy. My hand instinctively went between my legs, mimicking what was on the screen. It felt sooo good! I can't believe I spent the last few years such a prude!
Just as I was getting really into it, my mom called from downstairs for me to come get something to eat. I shut the computer down in frustration, cleaned myself up and got dressed. The rest of the night was spent with my mom, but I couldn't shake the desire to go back for more. I texted with Holly and Haley and they admitted to watching the sex videos too.
The next day, we rushed to my house after school. I still had to shave the twins, and I was excited beyond belief. In my room, Haley quickly stripped down. She had worn the old granny panties, and I just couldn't resist teasing her about it. She said she didn't want to wear the new ones until got her pussy cleaned up. I asked Holly if she was wearing the granny panties too and she just nodded slightly. She is way more shy than Haley and looked nervous about all of this.
I went into my bathroom and got everything needed and returned to find Haley sitting naked on my bed. I pushed her back so that she was laying flat, then raised her legs so that her feet were planted on the bed.
"So what's it going to be?" I asked, spreading her knees wide.
"I want to go bald," she said excitedly.
"Really?"
"Yeah, I love the girls in the videos like that. You can see everything!"
"OK, let's do it."
I began cutting her bush with the scissors to get it as close as possible before starting with the razor. My tugging on the hairs pulled her lips open a little bit and I could see the juices getting ready to drip out. I wanted to plunge a couple of fingers in, but we were all virgins and I had read that penetration is very painful the first time. Instead, I used my thumb as they guy in the video did and stroked up and down through the folds of her pussy. Haley moaned softly while Holly looked away in embarrassment.
I didn't play with her too long before squirting the shaving lotion on her crotch. My fingers pushed into her crease a little bit as the cream got smeared around and then I went to work shaving her bare. My juices started flowing too just thinking about how all the boys would love to be doing what I was doing right now. And being honest, it was arousing to me to be touching another girl like this. As the razor glided around, the moisture made her crotch shine. I had to reapply the lotion a couple of times due to the amount of hair but eventually got it all off. Using a towel, I wiped the excess water and stubble away to reveal her clean-shaven pussy.
Haley sat up and Holly leaned in to see. It looked good, but not as good as the girls in the video. There were already red bumps from the razor, so I went to get some moisturizer to massage into the area. Her glistening lips were engorged, and her clit was plainly visible, poking out from under its cover. I squirted the lotion on, gently massaging it around. Haley turned her hips slightly, causing my fingers to brush over her pussy lips. Her entire body tensed and stretched, pressing toward my circling fingers. She and I kind of realized at the same moment that maybe this was going further than we had expected. Haley relaxed and laid flat, and I removed my fingers. Both of us were blushing while Holly looked on with her mouth agape.
"The bumps will go away in a little while. We'll have to do some tanning when school is out. OK Holly, it's your turn," I said, trying to ease the discomfort.
Haley jumped up from the bed to look at herself in the full-length mirror. She twisted from side to side and ran her hand over the now barren area. A smile crept across her face as she turned to Holly.
"Your turn. Get those clothes off," I said jokingly.
She was nervous and scared, so Haley and I helped her. I grabbed the hem of her shirt and pulled it up over her head and off. Haley unbuttoned her jeans and we both worked them down to the floor. There were those stupid, ugly granny panties! I quickly yanked them down and tossed them on the floor several feet away. Haley unhooked her bra and threw it next to the panties. I then guided her over to the bed, sat her down and laid her back.
"So what will it be for you?" I asked.
"I... I don't want to shave it all off. Ma... maybe just trim it," she said nervously.
"OK, we'll start with that. If you want more, we can always go further," I said.
She covered her face with her hands as I used the scissors to first shorten the hair. Some of it was about two and a half inches long. She probably had never trimmed it in her entire life. But, I must admit that mine had been the same. Anyway, I started snipping, dropping tufts of hair on the towel next to her. Haley was watching intently. It was amazing how different these two had become personality wise recently. Holly is shy, introverted and easily embarrassed. Haley used to be the same, but since we started making ourselves over, she has become outgoing, bubbly and kind of daring. Apparently this was sort of a sexual awakening for Haley and I. Holly maybe just needed a bit more time.
Once the hair was cut to about an inch, I squirted some shave gel into my hand, placing it in her crotch. She twitched at first contact, either out of surprise or the coolness of the gel. Some of her hair spread out onto her thighs, so I rubbed the gel over it and reached for the razor.
"DON'T SHAVE IT ALL OFF!" She squealed.
"I promise I won't. You'll love it."
I proceeded to shave her thighs clean, not taking any liberties with her as I did with Haley because I didn't want to scare her off. Once her thighs were smooth, I made sure her pubic area was nicely shaped before wiping all the residue off. It looked fantastic! The light brown hair was wispy with highlights of blonde mixed in. It made me glad that we didn't shave it completely off.
"You want to see?" I asked, pulling her into a sitting position.
She looked down in wonder, a smile creeping across her face. She rustled her fingers through it and giggled.
"Come on. Get up," Haley said. "Let's compare."
Holly stood with Haley on her left and me on her right. We stared into the dresser mirror at the three naked girls. It was quite the contrast. I had a well-manicured black bush, Holly had a trimmed, light brown and blonde bush and Haley was completely bald. The transformation from nerdy bookworms to hot coeds was now complete.
"Let's take some pictures," Haley said excitedly as she reached for her phone.
"No way! I'm not doing that!" Holly complained.
"It'll just be for us. Nobody but us will ever see them," I assured her.
After an uneasy few seconds, Holly asked, "Promise?"
"I swear," Haley said. "Besides, you'll have pics of us too."
She took the first pic in the mirror of the three of us with our arms around each other. Then she started taking individual pictures of me. Close ups of my tits, butt and bush. I began doing some basic poses as she snapped away with her phone.
"Can I take some... with your legs open?" She boldly asked.
"HALEY!" Holly shouted.
I was stunned and now it was me who was embarrassed and hesitant.
"Come on! It'll be fun, just like the girls in the videos."
With a nervous sigh, I stood in front of her and spread my feet apart. She got down on her knees and held her phone up between my legs. The flash went off, then three more. She stood up, turned her phone to her face and scrolled to find the photos she had just taken. Holly slid up next to her to have a look.
"Oh, you're wet," she giggled with Holly joining in.
"You lie," I said defensively.
Haley held the phone up for me to see for myself. Holy crap she was right! My pussy was so wet it was ready to drip! I blushed, feeling stupid. Haley reached out and grabbed my arms, her phone pressing into my left arm. She turned me around and backed me up so that the back of my knees were against the bed. The she pushed me down into a sitting position.
"Lay back so I can get some better shots," she instructed.
My mind raced. Am I really going to do this? Before I could protest, she put the palm of her hand on my chest below my chin and pushed gently. I fell backwards, scared of what was about to happen, but not wanting to be a wimp. Haley dropped her phone on the bed next to me and grabbed my legs.
"Here, you take this one," she said to Holly.
Holly took my left leg and Haley picked up my right. Together they spread me open, lifted my legs, closed them and bent my knees up to my chest, exposing my pussy in every imaginable way while Haley continued taking pictures.
"Ooh look! She's all wet!" Haley said.
"Shut up!" I said defensively. "You lie."
I knew it was true because I could feel it. Even though I was scared and embarrassed, it was hot and I really wanted one or both of them to touch me. But at the same time, I didn't want them to know that.
"Are you still a virgin?" Haley teased.
"You know I am."
"How do we know? We aren't with you 24/7."
"Pretty damn close," I retorted, still spread eagle in front of them.
"Not good enough. I need proof," Haley said, ducking under my right leg and placing it on her left shoulder.
Holly continued holding my left leg, then Haley reached her left hand toward my pussy. Before I could even comprehend what was about to happen, her fingers touched my lips and spread me open. I had to stifle a little moan. No other person has ever done that to me.
"Oh, I think you might be right. I think I see a hymen!" She said as the flashlight on her phone bathed my crotch in a bright light. "Yes, yes you were being honest. Hold still for a sec and I'll document it."
Her phone clicked a couple of times signaling that she was taking more pictures. I took the opportunity to roll onto my side and extract myself from the very awkward pose. Haley sat down on the bed, staring at her phone with Holly sitting next to her. I scooted around next to Holly and together we looked at all of the photos Haley had taken of my pussy. My stomach did flip flops realizing someone had these photos of me.
"Just so you know, I'll fucking kill you if you show those to anybody," I said, half kidding.
"Don't worry. I got you girl. You know I would never do that."
"Come on, let's see the hymen pictures," Holly said enthusiastically.
Haley quickly swiped through the photos until she got to the first picture of my hymen. The room was silent as we put our heads together and stared at the screen. I have to admit I'd never seen a hymen before, let alone my own.
"Is that it?" Holly asked.
"I guess so," Haley replied, spreading her fingers on the screen to enlarge it.
"So what happens to it when you lose your virginity?" Holly asked.
"I think the guys dick pushes through it and tears it open. That's why they say it hurts so bad," I said.
"It hurts?"
"Yeah, but I think only the first time."
"What if you just stick your finger in there and do it yourself to get it over with?" Haley asked.
"You could, but your first time is supposed to be something really special." I said
"Fuck that. Really special for the guy, but it sucks for us," Haley said.
"So you think I should deflower myself?"
"Wellll... maybe we could help you," Haley said shyly.
"You mean you want to shove your fingers in me?"
"Well you don't have to make it sound like being raped. Obviously I haven't thought about the details but maybe it would be more gentle if we did it."
"I don't know. If I do it, you two are going to do it too."
"We don't have to do it now. Let's think about this for a bit. Besides, our moms will be home soon, so we better get going."
With that, we appeared to have reached an agreement to take each other's virginity, or at least think about it. Holly and Haley began to dress as I watched, admiring their sexy bodies and recently shaved crotches. That was until they pulled on those panties.
"Next time I see you two, you better not be wearing those granny panties!" I barked
They both giggled and finished dressing and left me sitting naked on my bed. I decided to check the internet for information about breaking my own hymen. Much to my relief, the article said it isn't necessary. The hymen naturally stretches over time & doesn't really break during sex the first time. The pain is usually minimal and probably not related to the hymen.
While that information was a relief, it was also a little disappointing. The thought of Holly or Haley fingering my pussy had me excited. I began to daydream about them fucking me with a dildo and rubbing my clit. Those girls in the porn videos sure seemed to love dildos.
With that in mind, I began searching sex toys on my computer. The assortment was staggering. Most of which I had no idea what they were for or what they did. My heart was thumping and my pussy was leaking just looking at those things. I tentatively put a real looking dildo in the cart, then came across a strap on. The picture showed a hot girl putting it on and my head went directly to thoughts of pushing it into Haley and Holly. Into my cart it went. Maybe that is enough for now, I thought. I grabbed my credit card and entered all of the information to check out and selected express delivery. My hand quivered on the mouse as I was about to hit the "complete" button. I almost chickened out, but then thought - what the hell, why not and clicked the button to complete the purchase.
Four days later, the three of us were coming home from school, laughing and celebrating because it was the last week before graduation. A delivery truck was pulling away from my house. A box sat on the front porch. My stomach leapt into my throat. I knew what that was, but my excitement turned to nerves.
"Hey, you got a package!" Holly said, picking it up. "It's addressed to you."
"What did you buy, girlfriend?" Haley teased.
"Oh... it's uh... nothing really," I said, trying to act nonchalant, but it wasn't working.
"Let's see!" Holly said, pushing my front door open and carrying the box to the couch.
"I'll open later. What do you guys want to do?" I tried to distract them.
"I want to see what's in the box," Haley laughed.
She pulled a nail file from her purse and sliced the tape on the box. The flaps popped up and she pulled out some paper packing, then her head turned to me in a flash.
"YOUUUU SLUT!" She beamed, pulling the dildo out of the box, wrapped in clear plastic.
I wanted to crawl in a hole somewhere. And she hadn't even seen the strap on that I assumed was also in the box. next she pulled out the strap on. I tried to grab it out of her hands, but she pulled it away from me.
"What is this? Who were you planning to use this on?" She asked playfully.
"I don't know. I just... it's stupid. I just thought... you know, never mind."
"Open them up!" Holly said enthusiastically.
Haley punctured the hard plastic wrap of the dildo with her nail file and sliced it open. She pulled it out and waved the dong in front of her. It was about eight inches long and flexible, so it flopped around in her hand.
"Do you think all of the boys look like this?" She asked, now beginning to rub her index finger in little circles around the head.
"I... I don't know. It is very real looking. I mean at least that is what the guys in the videos look like," I said.
"Let's try it out!" Haley said. "Get naked girlfriend!"
"WHAT! I'm not going to strip in my living room so you can fuck me with that thing!"
"Why not? Isn't that what we agreed - so it wouldn't hurt so much?" Haley asked.
"Wait, I read that the hymen doesn't really break, it just stretches and the pain is minimal, so maybe we don't have to do it," I argued. "Besides, why should it be me?"
"You're the one who ordered this stuff! It should be you to try it first." Haley shot back.
"Well I'm not sure I want to do it now."
"Oh come on. You got this far, might as well just do it."
"I'm NOT going to let you fuck me with that thing in my living room!"
"OK, let's go to your room," Holly said, scooping up the strap on, box and packing material.
Haley grabbed me by the arms, pulled me up from the couch and began pushing me from behind toward the stairs. I resisted half heartedly, but let her push me all the way up the stairs and into my bedroom. Holly was there pulling the strap on out of the box. It kind of looked like a jock strap with a fake dick sticking out the front. The dildo on it was a little more firm than the other one, but it still bent a little bit.
"OK, get your clothes off," Haley ordered.
"Wait, wait! I... I'm scared."
"Don't worry. I promise I'll stop if it hurts you. Come on."
I didn't move, I couldn't. Haley came over, pushed me down on the bed and pulled my shirt up over my head.
"Hey, why are you taking my shirt off?" I complained.
"Oh, get real. It'll be more fun if you're naked."
With that, she pulled my bra off, unbuttoned my jeans and yanked them down. I was left laying back on my elbows now wearing only a pair of pastel green panties in front of my two fully clothed best friends. I was so nervous I was literally trembling.
Haley stepped between my legs, hooked her index fingers in the waistband of my panties and peeled them down. After pulling them off my feet, she took a second to twirl them on her finger before tossing them onto my pillow. Now I was completely naked on my bed with Haley standing between my legs. She picked up the dildo and inched it toward my crotch.
"Wait, I think you need to lube it first," I protested.
"Here, this was in the box," Holly said as she tossed a bottle to Haley.
"Perfect!" Haley said, popping it open. I watched anxiously as she dripped the clear fluid over the head of the dildo. Her fingers worked up and down the shaft seductively, almost as if she had done this before. After a final few strokes over the knob, she pointed the glistening dong toward my pussy again. I laid back, placing my feet on the bed and closing my eyes in anticipation of pain.
When the tip first touched me, I flinched. It was cool, but not unpleasant. Haley rubbed it up and down the length of my slit a few times. The lube commingled with my natural juices, making my entire crotch slippery. I could sense Holly moving around to get a better view. Haley began pushing it against my pussy, then two fingers gently separated my lips. The head was now squarely at my entrance.
"OK, here we go. I'm going to push it in a little. Tell me if it hurts and I'll stop," Haley said.
I felt the pressure increase and instinctively tried to scoot away. Haley stopped briefly, then pushed again. Part of the tip was in me now. So far, no pain, but I was trembling in fear. She then rotated the dildo and moved it side to side to help loosen things up. Then she pushed a little more until I felt a stinging feeling. I gasped and tensed, placing my palms flat on the bed.
"Are you OK? Does that hurt?" she asked.
"Just a little. I'm more scared than anything. Keep going," I said.
My hole stretched and stretched as Haley pushed further. There was another short, sharp pain and she stopped the forward pressure again to let me adjust. The forward motion continued slowly. I felt completely full, like there was some sort of giant pipe inside me.
"That's it! It's in," Haley said. "Do you want me to... fuck you with it?"
"O... OK, but go slow," I said.
Haley pulled it back slowly, then slid it in again. She held it buried for a couple of seconds, then pulled it back and immediately pushed it in a bit faster this time. I started writhing on the bed at the strange feeling. I can't say it was blissful pleasure, it was more like my pussy was choking. On the other hand, it wasn't unpleasant either.
"There's a little bit of blood," Holly said. "Are you alright?"
"Yeah, I'm fine," I half grunted. "It's getting better and better."
Haley began twisting and moving the dildo up and down, stretching me to the limit while continuing to run it in and out of me at a moderate pace now. With each stroke, the feeling became less awkward and more pleasurable. Then she stopped and withdrew the dildo completely.
I opened my eyes to find her holding the shiny dick up in front of me. It had a little bit of blood on it, but it was much less than expected. I had thought it was going to be like my period. The pain was minimal and it had actually started to feel pretty good. Mission accomplished.
"Now do me!" Haley said, dropping the dildo and stripping off in a flash.
Before I knew it, she was whipping her lavender, lace panties to down and tossing them at my head. I was thrilled to see she had given up the granny panties. I picked them up as I rolled off the bed and found them completely soaked.
"Your panties are all wet. Did you like fucking me with that cock?" I said teasingly.
"Yeah, it was hot," she replied taking my place on the bed. I thought my comment would embarrass her, but apparently she was too horny to care.
Holly took the dildo to the bathroom and washed it off. It was funny watching her handle it. Obviously she had never had anything like this before and she seemed to enjoy rubbing it and looking at it. She soaped it up and cleaned it thoroughly, then brought it to me. I held it up for her to drip some lube on and then smeared it all around.
My heart raced again as I was about to stick this thing into my bff. Her crotch was completely bald and shining with her juices. I placed the dildo against her lips and to my surprise, she instantly pushed her hips forward, engulfing about three inches.
"Oh, sorry," I said, thinking I pushed too much.
"It's OK. Keep going," she said.
At first I was confused. Why didn't this hurt her? Why was there no blood?
"You little wench! "You've done this before, haven't you?" I gasped.
"Kinda," she giggled.
"When did you do that?" Holly asked in disbelief.
"I... I've done it a couple of times."
"Wh... what did you use?" I asked.
"The handle of my hairbrush. Keep going."
I pushed it all the way in to the fake balls at the bottom. Haley sighed and groped her tits. I withdrew it until it was almost all the way out, then mimicked her movements in me. I twisted and turned it, pushed it in and pulled it back as she squirmed on the bed under me. I picked up the tempo and started ramming it in at a pretty good pace.
"Mmmmmm!" she moaned.
I took a few more strokes, as she began to pant. Thinking it might be too much, I abruptly stopped and pulled the fake cock all the way out. Haley melted into a limp puddle on the bed.
"Are you OK?" I asked.
"Yeah, that... that was great," she said, gasping for breath.
"Did you orgasm?" I asked in a sort of accusing tone.
"I... I don't know. I don't think so."
We all just sat there in silence for a couple of minutes while Haley recovered. I wanted to ask more questions about what she had done by herself, but before I could, she sat up and looked over to Holly.
"It's your turn."
She looked really nervous and uncomfortable. She is much more shy than Haley and was beet red.
"Maybe we should wait. It's getting late," she said, trying to stall.
"Come on, let's just get it over with. I promise you it's not bad at all. Unless... have you done it before too?" I asked.
"N... NO!" she responded, almost offended that I would ask.
"OK, then come on. You don't want to be the only one that isn't ready," I pressured.
She didn't respond, so I decided to help by grabbing the hem of her shirt a lifting it. There was no objection, so I pulled it over her head and off. Haley ran to the bathroom to clean the dildo as I unbuttoned her jeans. She let me take them off to reveal her black satin panties. Hopefully she too had given up the granny panties for good!
I worked her panties down just as Haley returned with the freshly cleaned dildo. Holly's pussy was wet too, but I didn't remark about it for fear of embarrassing her to the point she would put a stop to it. Haley lubed the dildo and handed it to me.
I knew I would have to take it extremely slow with Holly, so I just rested the tip against her pussy for a minute or two. Slowly, I began to apply a little pressure and the tip slipped in. She winced so I stopped the forward movement. When she seemed prepared, I pushed a little more. She winced again and I stopped. There was no blood yet, so I suspected it was mostly fear.
She relaxed and I pushed again. This time, she let out a little yelp and a trickle of blood appeared. I waited patiently for her recover, then applied some more pressure. Her face remained contorted, but she wasn't crying in pain. I continued pushing until the fake balls rested against her butt.
"It's in! You did it!" I exclaimed.
Holly sat up to where she was resting on her elbows to get a look. I pulled my hands away so she could see the dildo buried inside her. A smile crept across her face.
"How does it feel?" Haley asked.
"It doesn't hurt anymore, but it is a little uncomfortable."
"Do you want me to... move it?" I asked.
"N... no, I don't think I'm ready for that yet."
"That's ok, do you want me to take it out?"
"Yeah, that's enough for the first time, I think."
I slowly withdrew it and set it on the bed as Holly fell back to relax. Haley and I joined her and the three of us laid there, naked on the bed together. I don't know about the twins, but I dozed off, awaking to a car horn on the street. I rolled over to look at the clock. It was almost 5:30.
"Hey, wake up," I said, jostling Haley. "Our moms will be home soon. We better get dressed."
We all got up in a groggy haze and slowly dressed. It was awkwardly silent until Haley slapped my ass as they walked out of my room.
"See you later hot stuff," she said.
The next few days at school were very different for me. I found myself really checking out the boys and getting worked up. It was the last week before graduation and all the guys already had girlfriends, but I couldn't help daydreaming about what they looked like naked. Haley sometimes jabbed me with her elbow as we passed a cute guy in the hall, so I know she was feeling the same thing as I was. I even caught Holly eyeing a few.
Each day after school, we would rush to my house and turn on the computer to watch porn movies until our moms got home from work. Each of us had received the talk from our mothers about protection etc., but most of our information on sex came from porn. We spent a couple of hours a day watching and learning.
It was interesting to see what kind of kink each of us had. I myself was turned on most by watching the guys use big dildos on the girls. There was something about the man being in control, relentlessly shoving it in that set me on fire. Even better if the girl was tied!
Haley gravitated to hand jobs, blowjobs and cock teasing. She seemed fascinated with the penis and always commented on whether she liked or didn't like the looks of all the cocks. She even described some of them as beautiful and licked her lips when she saw the clear fluid leaking out.
Holly was the most surprising. As reserved as she was, she got turned on by watching pussy licking! It didn't matter if it was a man or a woman doing the service. She would move closer to the monitor to get a better view of the girl writhing around in ecstasy.
I thought it was a bit odd that none of us was most interested in conventional fucking. Maybe that was just because none of us had ever actually done it and there was a little fear yet. Holly and I were turned on most by being somewhat submissive, while Haley like the more dominant role.
When we finished the last day of school, we raced to my house again. The three of us were so thrilled to be done with high school and getting ready for college where we could develop a real social life. I was so horny when I turned on the computer, I stripped off all my clothes before sitting down in front of the keyboard. Holly and Haley were a little taken aback because until now, we had always been fully clothed while watching porn.
I brought up our favorite site and began scrolling for something that excited me. Haley appeared standing to my right side. She was now naked too. My heart was pumping, not knowing what was about to happen. I looked behind me to see Holly still fully clothed, fidgeting uncomfortably.
"You might as well join us. We're just having fun. Besides, don't you want to let go a little bit?" I asked.
She nervously pulled her shirt off and I turned my attention back to the screen. I found a spring break video that looked interesting and clicked on it. There were five girls and three guys in a hotel room. Two of the girls were naked on the bed with two naked guys. The blonde girl was on her knees stroking the cock of the guy standing beside the bed. A brunette was standing on the opposite side of the bed, preparing to shove a dildo into the blonde from behind. The other naked guy walked up behind the brunette and bent her over just as she pushed the dildo into the blonde. The blonde took her hands off her guy's dick and engulfed him with her mouth. The guy behind the brunette lifted her so that she too was kneeling on the bed as she rammed the dildo into her friend. The guy then began licking her pussy from behind. Two other naked girls were head to toe licking each other and the other guy and girl were off screen.
This was perfect! It had something for all of us. Dildo slamming for me, hand job/blowjob for Haley and pussy licking for Holly! There was movement on my left side. Holly, now naked too had moved next to me. I reached over and gently stroked her pussy hair with my thumb and sawed my hand between her lips. I scooted my chair back a few inches to make it more comfortable for me, then reached over to Haley. My thumb landed directly on her clit since she was shaved clean.
So we continued watching the video with me fingering my naked best friends standing on either side of me. Haley started moving her hips in little circles to accentuate my diddling. Holly noticed and copied Haley's actions. My hands were soaked with their juices as their moans and sighs mingled with those of the girls in the video.
Just as the twins were really starting to pant, the guy getting the bj in the movie came all over the blonde's face. The guy behind the brunette grabbed his cock and jerked it furiously until he came all over her ass. They all collapsed onto the bed with the girls giggling and laughing.
Haley disengaged from my fingers, grabbed me by the arm and pulled me out of the chair. She pushed me down on my bed and stood between my legs. Her bald crotch was glistening with her juices.
"Where's the dildo?" She asked.
"In my top dresser drawer," I replied breathlessly.
Holly quickly went to the dresser and retrieved it, handing it to Haley. Without any hesitation at all or any playing around, Haley pushed the fake cock into me as far as she could. She immediately began fucking me with it passionately. My hands were flailing, so Holly climbed on the bed and held my arms down. My kink was playing out!
After a few seconds, my body began to tremble and then tensed. I started gasping for breath and my hips bucked up violently. Haley backed off, leaving the dildo buried in me as my hips bucked again.
"TAKE IT OUT!" I grunted.
She reached in and pulled the dildo out quickly, causing my entire body to go into spasms. I flopped around on the bed, throwing Holly off my arms. The pressure in my pussy was so intense, it felt like a bowling ball was in there. Then, POP! Like pulling the tab on a shaken can of soda, I exploded. Everything went black.
"Oh my god! SAM! SAM!" Holly screeched.
"Are you OK? What the fuck just happened?" Haley asked, looking into my bleary eyes.
"I... I don't know," I said, confused and exhausted.
"Did you pee?" Haley asked.
"I... I think you had an orgasm," Holly said.
Haley's chest and stomach were dripping wet. She smeared it around with her hand and smelled it.
"It doesn't smell like pee."
None of us had experienced an orgasm that we knew of, so we weren't sure that's what happened. There wasn't any time to figure it out right now. Our moms would be home soon. My bed sheets were wet and the room smelled funky. I stripped the bed, gave Haley a towel to clean off with and threw everything in the washer. The twins dressed and headed next door.
That night, I opened the porn site to look up girl orgasm. There were tons of videos that convinced me I had actually experienced my first orgasm. Most of them referred to it as squirting. I quickly texted the twins so they could check it out. They agreed that I was the first of us to reach this milestone. I went to bed that night wanting to experience it again. It was the most intensely wonderful feeling I've ever had!
On Saturday morning, Holly and Haley showed up at my door with their graduation gowns. Tomorrow it would be official. We were going to be graduates heading to college! We hurried to my room, wanting to mess around some more, but my mom was home. Holly mentioned that their mom was taking them on a vacation for a few days starting on Monday. I was disappointed that our fun would have to wait. They weren't too thrilled either but understood this might be the last time they get to spend quality time with her.
Since we couldn't safely watch porn and play naked, we all were feeling a little devilish. We talked about going naked under our gowns, but ultimately agreed that was too risky. Instead, we decided to wear only our sexiest bra and panties. This way, if we were exposed, we could simply say that we thought the gown was like a dress and didn't know.
On Sunday morning, I went to the twins' house to get ready. The butterflies we swarming in our stomachs as we slipped on our lingerie. Holly had a lacy white bra and silky white panties with a pink bow in front. Haley had the same only in black with a black bow on the panties. I had a baby blue set. Holly slid her gown on, the shiny white panties and bra looked fantastic against the royal blue gown. Haley's black underwear wasn't as stark a contrast, but was still sexy as hell. My blue lingerie made a nice combination too.
We made our way downstairs to find several family friends had arrived. Our parents had a joint post graduation party planned with food and drinks. They took a lot of pictures with the three of us smirking at each other as we hid our secret. Then, we loaded up and went to the football field for the outdoor ceremony. It was a bit windy and our gowns fluttered around, so we had to be careful not to flash our undies. Otherwise, the event was rather mundane.
When we got home, the back yards were decorated and table set up for food etc. Everybody wanted more pictures. We obliged for a few minutes, then my dad asked me to take off my gown for some pictures. My heart just about stopped! I looked over to the twins and their eyes were as big as saucers.
"Uh, OK, I need to go change first. I just have sweat pants on under here," I stammered.
The twins and I scampered into their house, giggling all the way up the stairs to their bedroom. We took off the gowns and playfully slapped and pinched each other for a minute before reluctantly putting on some appropriate clothes and rejoined the party.
I actually had a lot of fun seeing family and friends and just celebrating the accomplishment. As evening approached, guests started heading for home and I was worn out. We all pitched in to help clean up. I said goodbye to my dad and the twins did the same with theirs. Everyone was gone. I realized Holly and Haley would be leaving in the morning and told them I couldn't wait until they got back.
Back at home, I went to my room and thought about the computer, but I was just too tired. I laid down and fell asleep in no time. I awoke to a car horn and peeked out the window to see the twins leaving with their mom. We waved at each other as the car backed out of the driveway. Crap, what would I do now? Mom was at work and nobody else is around.
I showered, dressed and had some cereal for breakfast. I didn't expect to feel depressed on my first day of freedom from high school. The sun was shining and it was already starting to get hot. I decided to go sit on our front stoop and check out social media and maybe text with the twins.
I had been sitting there for about 10 minutes moping when Tommy came walking up the sidewalk pulling a lawnmower and carrying a gas can. Oh yeah, our moms hired him in the summer to take care of the lawns. I think he did several other houses in the neighborhood too.
Tommy was in our graduating class. He is rather shy, strange and awkward. I would say he is about 5'9" and skinny, maybe 130 lbs. He didn't work very hard on his appearance, but could be considered cute if he just tried a little. Even with this, he had a girlfriend, Kelli. One of the cheerleaders no less. I'm not so sure they were really much of a couple though. She always seemed disinterested in him and he just followed her around like a little puppy. I guess she just didn't want to be someone who didn't have a boyfriend.
I kind of felt sorry for Tommy. Outside of the fake relationship with Kelli, his father has never been around and his mother was an alcoholic. He ended up getting a DUI and lost his driver's license. I suspect they didn't have a lot of money, but he always had respectable clothes and frequently bought food at the cafeteria instead of eating school lunch. He did odd jobs around town too, so at least he wasn't destitute.
I continued scrolling social media for a few more minutes while Tommy gassed up the mower. I nodded in acknowledgment of him as he put the gas can aside and prepared to start the mower. All of a sudden, I felt a sharp, excruciating pain in my back. I shrieked, jumped up and ran into the house, dashing up the stairs to my bathroom. I quickly pulled my shirt over my head to see a huge bumble bee tumble to the floor. I turned my back to the mirror, but didn't see any obvious signs of a sting. The pain was still sharp under my bra strap though.
"S... Sam! Are you OK?" Tommy called from the front door.
"Tommy, come up here. I need your help," I called back, not really realizing that I was shirtless with only my bra on top.
A few seconds later, Tommy tentatively poked his head in the door of my bedroom and said nervously, "Sam?"
"I'm in the bathroom. I got stung by a bee. I need you to help me."
Then, he was at my bathroom door. Our eyes met in shock as he found me in only a bra on top and I finally realized I was somewhat exposed to my classmate.
"S... sorry," he said. "I'll go."
"No. Just come here. That damn bee stung me, but I can't see it. What does it look like?" I said turning my back so he could look.
"I don't see anything."
"There has to be something, it hurts. It must be under my bra. Look under it."
"W... what?"
"Just do it!"
After a moment's hesitation, he gently reached toward my back and grasped my bra between his thumb and forefinger. I felt the bra move upward slightly.
"Oh crap! Yeah, it got you good. It's red and swollen."
"There's some hydrocortisone cream in the drawer. Is the stinger still in there?"
I could feel his hot breath on the middle of my back as he moved in close to get a look. His fingernail scraped across the area, causing me to yelp.
"Got it."
His hands left my back and the bra slipped down over the sting as he tried to locate the cream. It felt like a red hot needle poking me. He rummaged around in the drawer, then held up a tube of cream, asking if that was the right one. Instead of answering, I took it from him and took the cap off and handed it back. I could literally feel his hands trembling as he lifted the bra strap again. Then, the soothing cool of the cream spread over the area. I sighed in relief. My eyes glanced up to the mirror, catching Tommy staring at the reflection of my bra covered tits. My bra was a dainty, white lace one that if you looked hard, you could see the faint outline of my nipples. He immediately averted his eyes back to my sting, so I don't think he actually saw anything.
The cool sensation had dissipated now and his rubbing was actually increasing the pain. I leaned forward to pull away, which caused my butt to move back into his crotch. He had a hard-on! I had never seen or felt a real one before, but there was no mistaking this. He quickly backed off and turned to exit the bathroom.
"Wait, it still hurts," I said.
"You need to put some ice on it. Do you have an ice pack?"
"Yeah, OK. Will you help me?"
I slipped past him and he followed my down the stairs to the living room. I dashed into the kitchen, fishing an ice pack out of the freezer. Now I was a nervous wreck. Do I just walk back out there like this? There really was no choice because my shirt was on the floor of the bathroom. I didn't want to make it seem like a big deal by putting my hands over my tits, so I screwed up my courage and as calmly as possible walked back to the living room. Tommy looked up, seeing me without the shirt from the front for the first time.
I sat down on the couch, slipped the ice pack into the pouch on the strap and tried to maneuver it over the sting. But the sting was in that spot on my back that I couldn't reach. The strap was all twisted and the ice was not in the right place. It was starting to burn again.
"Here, you're going to have to put it on," I said handing it to him.
He took it and straightened it out. A small wet spot had formed on the front of his shorts. Was that his dick leaking? Or maybe it was just moisture from the ice pack. No, the spot was growing right before my eyes and I could see movement as his boner poked against his shorts! He leaned in toward me, putting the pack behind my back with his right hand and reaching his left hand behind me to search for the other end of the strap. His chest was right in my face. My heart was thumping, knowing that Tommy was sexually excited.
"T... turn around so I can lay it flat," he said.
I turned sideways and jumped as the cold pack contacted the sensitive skin on my back. He wrapped the strap around and pressed the velcro together just under my tits. He stood up straight and the strap immediately slipped down.
"That's no good. It's going to fall off. Put the strap over my shoulder."
He reached in and ripped the velcro apart and pulled the strap over my shoulder. Now he had a dilemma. The strap would have to go right between my tits. His hands were visibly trembling as his fingers got closer and closer. He hesitated, not knowing if he should go any further.
"Just do it," I urged. "They won't bite you."
He quickly reattached the velcro and backed away. The wet spot on his shorts had doubled in size. His eyes followed mine to his shorts and he too noticed it. His face turned red and he began backing toward the door to escape.
"Wait! Wait! Are you sure the ice is over the sting? It's getting worse," I said.
He tentatively walked back over and looked behind me. "Y... your um br... bra is on top of the sting."
"Well fix it," I whined in pain.
He fumbled around in back, but couldn't make it work. He was obviously nervous and uncomfortable, so I undid the velcro, letting the pack fall to the couch. Tommy tried different ways to get it over the sting, but was having no luck.
"Run the strap under the bra, you dummy!"
I heard him take a deep breath, then felt my bra being pulled away from back. I was really beginning to enjoy the tease I was giving him, even though the sting was still painful. Then, there was a snap and all the tension in my bra released. The clasp had come undone, or broken! I quickly clamped my arms together to keep it from falling off completely.
"What happened? Did it break?" I asked.
"I... I don't kn... know."
"Well put the ice pack on and then we'll deal with the bra," I instructed.
The ice hit my back again, causing me to flinch. He lifted the strap over my left shoulder, guiding it between my breasts again. His hands were shaking so bad, he could barely hold onto it. He stopped when he got to my right side. The velcro was under my arm, which was holding my bra in place. I lifted my elbow to clear some room, but the bra stuck to my arm, which caused it to pull away from my right tit. I definitely saw my nipple, but wasn't sure Tommy could see it. He didn't say anything anyway. Once he had got the velcro closed again, the cold finally began to soothe the sting.
"Will you fix my bra?" I asked turning my back to him again.
He fumbled around back there for several seconds before getting it secured again. I swung my legs up on the couch and laid back. My nipples could be clearly identified poking out against the bra. Tommy turned and headed for the door. I didn't want him to go. It was fun teasing him and I was getting turned on too.
"Tommy wait! I'm feeling a little woozy. I'm not sure if I'm allergic to bee stings. Would you stay with me for a while?"
"Can't you just call your mom?"
"She's at work and I don't want her to come home for this. Just come sit with me for a while."
He hesitantly came over and sat down at the opposite end of the couch, pulling out his phone. He scrolled through it for a couple of minutes while I tried to think of ways to make him more uncomfortable. I stretched out my legs and put my feet in his lap. The wet spot on his shorts was cool on my heel. I arched my back as if to stretch, thrusting my chest out. Poor Tommy was trying his best to get a look while pretending to look at his phone.
"Would you go get me a soda from the fridge and maybe make me a peanut butter sandwich?"
He set his phone on the couch and went to the kitchen, again trying not to be obvious at getting a look at my bra covered tits and smooth belly. Once he was in the kitchen, I snatched his phone up before it could go to sleep and started snooping through it. He had Facebook open, but there was nothing interesting, so I opened his photos.
HOLY SHIT! There were dozens of pictures of his "girlfriend" Kelli that she clearly didn't know he took. The first couple were cleavage pics from over her shoulder, nothing too bad. Then there were about 10 pictures of her laying back on her couch with her right leg up, foot on the cushion reading some sort of book. The shorts she had on were loose fitting and her white panties were visible underneath. The shots were from all different angles, trying to get the best look.
"Hey, where's the peanut butter?" Tommy shouted from the kitchen, startling me into dropping his phone.
"Uh, it's in the uh cabinet above the toaster," I stammered.
Quickly grabbing his phone again before it went dark, I continued searching the photos. I found some voyeuristic shots of her in her cheerleading uniform with a good view up the skirt. The next photos truly shocked me. The images were of her reflection in the mirror standing in front of her bathroom sink doing her hair wearing only a bra and panties. I guessed she was getting ready to go out while Tommy waited and he must have snuck into her room.
Kelli wasn't supermodel gorgeous, but she had a smoking hot body. Her white, shimmering bra bulged with ample breasts and her butt protruded sexily in her white, blue striped panties as she bent slightly forward over the sink. There were tons of these pictures taken in quick succession. The ones where she was standing straight up offered a view of her mound bulging under her panties. I spread my fingers on the screen to enlarge one shot in particular, looking closely at her crotch.
"Here you g..." Tommy appeared in front of me with a soda and sandwich.
He looked like a deer in headlights as he tried to swipe the phone from my hands.
"That's not what it looks like!" He said.
"Oh, well what do you think I think it looks like?"
"It's nothing. We were just playing around."
"Come sit down," I said swinging my legs off the couch and patting the seat next to me.
He reluctantly sat next to me, but left a lot of space between. I scooted over so that our upper bodies were touching.
"C'mon Tommy. You guys weren't fooling around. She doesn't know you took these pictures, does she?"
"Well, I didn't mean any harm. I haven't ever shown them to anybody, ex... except now, I guess.
I continued scrolling through them with Tommy looking on. None of the pictures showed any actual nudity, but Kelli certainly wouldn't be happy about them regardless.
"Does she shave her pussy?" I asked with a giggle.
I... I d... don't know," he said with an air of frustration.
"YOU GUYS HAVE NEVER HAD SEX! ARE YOU A VIRGIN?" I gasped.
"NO!" he replied defensively.
"Be honest Tommy. Do you want me to ask her?"
"OK, OK. I've never had sex. Leave me alone."
"Relax. It's nothing to be ashamed of. I've never done it either," I said, wondering to myself if the dildo counted.
Tommy's eyes began stealing glances at my bra covered tits again. I realized I may have given him the idea that it might happen right now. I had no intention of that, so had to think of a way to get his mind off of it.
"Why don't you go make yourself a sandwich and we'll eat together?"
"No, I'm not hungry."
"Just do it. Trust me, it'll make you feel better."
He sighed, got up and went to the kitchen, trying to hide the ever growing wet spot on his shorts. I quickly selected all of the photos in his gallery, copied them to a zip file and found his email. In a few clicks, I had emailed the file to myself. I wasn't sure what I was going to do with them, but, just wanted to mess with him a little. I also put myself as a contact in his phone.
Tommy returned in a couple of minutes with a sandwich for himself and sat down beside me again. He saw that I was still looking at the pictures of Kelli.
"Can you just give me my phone back now?"
"Tommy, have you ever seen a real live girl naked?"
"Pffft! Yes."
"Tommy?"
"OK, no."
"Kelli never let you do anything?"
"She's a wench. Every time I tried to even kiss her, she always put me off. She was just using me so she could say she had a boyfriend. Besides, she broke up with me anyway."
"Oh, well I'm sorry about that. I kind of thought that might be the case. But maybe I can help you out."
"Wh... what do you mean, help me out?"
"Well, maybe we can fix you up, make you more attractive to girls, get you some confidence. We can fix your hair and get you some nicer clothes and just make you more presentable."
"Why would you do that?"
"Why not? So?"
"I... I don't know."
"I promise it'll be the best thing that ever happened to you if you say yes. You'll get to see your first naked girl! But you'll have to earn that first. Soooo?"
"OK, I guess."
"Good. Now go finish your jobs and I'll be in touch," I said, walking him to the door. "By the way, I copied all of those photos on your phone."
I pushed him out the door and closed it behind him, leaving that thought in his head. My heart was beating fast as I began thinking of how to make Tommy my own personal toy. I watched him start the mower and get to work on our grass.
While Tommy was working on the lawn, I put some laundry in the washer and changed into my swimsuit for some back yard tanning. I knew he would be coming around back soon and thought seeing me in a bikini would lure him in even more. I picked a plain white suit because it looked a lot like underwear and slipped out back setting up my lounger.
The mower droned on in front, stopping occasionally to empty the bag. I slathered on sun screen and laid back with my phone, sending a few text messages to Holly and Haley. There was no reply from them right away, so I just relaxed and enjoyed the sun. I decided not to tell the twins about my plan for Tommy just yet, thinking it would be a fun surprise for them when they get home.
After 20 minutes or so, the sound of the mower started to come around the corner. I watched for his reaction through my dark sunglasses. At first, he didn't see me, but when he turned to make another pass, he stopped abruptly, staring my direction. When I moved slightly, he snapped out of it and continued his work. He was absolutely checking me out every time he went past.
I got up to put the clothes in the dryer, teasing him by bending over to straighten the towel on the lounger before going inside. My crotch was damp from either sweat or excitement. This was fun. I quickly threw the clothes in the dryer and scurried back outside. He was watching closely again, so I waited until he passed in front to sit down and throw my legs over the lounger. He got a perfect crotch shot for just a moment.
Once he finished mowing, he got the string trimmer, meticulously getting every nook and cranny. Then he got the blower to clear off the clippings. I had to laugh because he managed to turn a half hour job into more than an hour. When that was finished, he timidly walked over to me. Just then, the buzzer on the dryer went off.
"Tommy, would you be a dear and fold the clothes in the dryer for me? I'm covered in oil."
"Uh, yeah, I guess so."
He slid the door open and went inside. I waited a couple of seconds to sneak up and watch him, knowing that the laundry was full of delicates. He appeared a few seconds later carrying the loaded basket to the living room. It was already obvious he knew what was in there. He looked toward the door and I ducked back so he wouldn't see me. When I peeked in again, he had a pair of my new panties stretched out between his fingers. The dainty white panty shimmered in the sunlight. Then, he crumpled them up and put them to his nose! Got you now, I laughed to myself. I quietly slid the door open and crept closer, then casually walked toward him.
"Like those do you?"
"Uh, n... no. I wasn't... I didn't mean to..."
"It's OK. See, if you want to continue with this, you just have to agree to be my little boy toy. Interested?"
"Wh... what do you mean?"
"You just have to do whatever I say. I'm not going to make you rob a bank or anything. It'll just be fun stuff," I said, spreading my feet apart a bit so he could get a good look at the gap between my legs.
He gulped then said, "Yeah, O... OK."
"Well, let's make it official. There's a note pad and pen on the kitchen counter. Bring them to me."
The wet spot on his shorts reappeared as he lumbered to the kitchen and returned.
"Write this down. 'I Tommy agree to do whatever Sam says, no questions asked. I understand that I can stop at any time, but if I do, the agreement is void and will never be offered again.' Did you get all that?"
He read it back and looked at me with concern.
"I'm not forcing you to do anything. If you want to do it, sign the paper. If not, tear it up and we'll never speak of it again."
He hesitated for a long time, then signed the bottom of the paper. I held out my hand and with trembling fingers he gave it to me.
"Wait, you're not just going to make me do chores, are you?"
"Well, you're free to back out any time. Just tear this up. But before you do, realize you've already got to see me in my bikini and play with my panties. Isn't that a good start?"
"Yeah, OK. I still get paid for cutting the grass right?"
"Certainly, how much does mom pay you?"
"$40."
I strutted to the kitchen and got his money out of the drawer, swaying my hips provocatively. He followed me half way and I slapped the money into his hand.
"That's enough for today. What are you doing tomorrow?"
"I have to cut your neighbor's lawn," he said nodding his head toward the twins' house.
"Good. Now get out of here," I said playfully smacking his butt to guide him toward the door.
TO BE CONTINUED
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