Left Alone

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Tommy plays dress-up and gets caught by his neighbor.
4.1k words
4.64
331.4k
183

Part 1 of the 2 part series

Updated 10/25/2022
Created 04/06/2007
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fantaseeboy
fantaseeboy
1,602 Followers

My parents had been out of town for 4 days and weren't expected back from their trip to Africa for another 3 weeks. I had been keeping myself quite busy since they left. On my first day alone, I took a long, hot bubble-bath and shaved off most of my body hair. Just above my cock, I cut the hair really short and left a thin "landing strip" like the girls on the internet.

My older sister, Teri, decided to stay at college over the summer break which left her old room unsupervised. After my bath, I put on a fashion show for myself. I think I tried on every outfit in Teri's wardrobe.

I had been oh-so aroused by girl's clothes for as long as I could remember. Every chance I got I would slip into my Teri's room and try on some of the trendy, sexy outfits she was so fond of. During no other time, did I feel so complete and sexy. I longed to wear skirts, dresses, stockings, bras, panties and heels ALL the time.

With no other obligations, I spent the next few days dressing up as a girl. I experimented with make-up and even found my longish blonde hair looked really cute in pigtails. As far as my petite cock was concerned, it was the best time of my life.

During the day I spent most of my time laying out, working on my tan. The wooden fence around our yard gave me a sense of privacy. I had found a teeny-tiny bikini in the bottom of Teri's dresser, our parents would never have approved of it. The little white triangle of fabric barely covered my cock and marble-sized balls. The thin strings ran from either side of the triangle, looped over my hips, joined together and disappeared between my tight, 19 year old cheeks. The two triangles on top were just large enough to cover my large-ish boy nipples. The same thin strings held the top together.

Dressed like this, laying on a lounge chair, coated in suntan oil with my white heels resting nearby is how Walter found me. He had come over to borrow a tool from my Dad's shed.

I didn't notice him until he was near enough to cast a shadow over my 5'6", 125 pound body. As I opened my eyes, shock, terror, humiliation and a million other feelings overtook me. I quickly shifted my hands to cover both my bikini bottoms and the tops. I stuttered and mumbled some lame excuse for being dressed as I was. OH GOD! What if he tells my parents? I was totally freaking out and just about to cry.

Walter just stood there, staring down at me. He is a big guy, at least 6 foot and in pretty good shape from a guy my Dad's age. The chiseled jaw line and strong eyes were what made him appear so intimidating at the moment.

After several moments of silence while his eyes studied every nook-and-cranny of exposed body, he avoided my attire by simply asking, "How are doing, Tommy?"

After biting my lower lip and shifting my hands to better cover myself, I answered "Fine." His eyes met mine and for some reason, I suddenly felt a little relaxed.

He said that he stopped by to borrow a tool (of some kind) from my Dad. I told him to help himself, motioning toward the shed with my chin. He slowly turned and walked to the shed. As soon as he was out of site, I flipped over on my tummy to hide the modest bulge in my bikini bottoms. Why I didn't run inside is beyond me!

His eyes were back on me as he stepped out of the shed with a wrench of some kind. He took a seat in a deck chair right beside my head and said something meaningless about the weather. After some more small talk, he casually mentioned that my tan was coming along nicely. I'm sure I blushed deeply.

At this point, I felt flattered that he noticed. Walter had always paid special attention to me, noticing the smallest things like a new hair style or new shorts, he never ignored me like my Dad's other friends. And the attention he was paying me now was starting to turn me on.

My reaction to his comment about my tan must have encouraged him as he went on to flatter me about my smooth, tight skin, toned muscles and finally my butt. That last one didn't really surprise me. My "friend" Derrick has always said I had a cute ass, it's more like a girls than a boys. My waist slid inward slightly then flared out to my hips which formed my perfect little heart-shaped bubble butt.

With the compliments flying, my little cock had become quite hard. The idea of him telling my parents anything had completely left my mind. I had always thought Walter was good looking for an older guy, but now I was finding myself glancing down at the man-sized bulge in his jeans. My god it looked HUGE, and it wasn't even hard!

As he stood up to get home and fix whatever it was he was working on, I stunned myself by rolling onto my side exposing my entire front to him. As we said goodbye, he turned and started to walk away. Very suddenly, he stopped and turned back toward me. He said that since I was all alone, and so was he, perhaps I would like to come over to his house and watch a movie tonight.

After I agreed, he smiled and asked me to "wear something pretty". I coyly smiled back at him and asked "Why?" He casually responded that my parents would eventually come home and I should take advantage of my freedom while it lasted.

As the gate shut behind him, I think I squealed with joy. I knew it wasn't a date and I shouldn't expect too much, what with Walter being my Dad's friend. But Derrick had been visiting colleges for the past week with his parents and I felt neglected.

We didn't set a time to meet, and I was so anxious, I trotted inside and took a nice long shower and re-shaved myself, just in case. The next hour was spent trying on different outfits, I had no idea what to wear. I felt like girl getting ready for a big date, it was wonderful!

I had everything from formal to casual to sexy at my disposal. Being August, it was scorching hot outside, even at night, so that ruled out the formal wear. I was NOT going to wear pants on my first time out dressed as a girl, so that ruled out most of the casual wear. What I finally decided on wound up being on the slutty side. I slipped into a white thong with small pink flowers on it, being especially careful to tuck my cock back between my legs. The tight pink tank top clung to my chest while leaving my mid-riff exposed. Following that, I found a thin, white cotton skirt. The skirt was tight and hugged my slim figure. When stretched around my body, it became sort of see-thru, enough to see the white panties against my tanned skin.

After pulling my hair up into pig-tails and applying a heavy coating of lip gloss, I looked like a school girl tease.

My stomach started to feel queasy as I realized I was really going to do this. I went to the kitchen to find something to eat, there wasn't much that didn't need cooking. I opened the candy drawer and found a lollipop, perfect! I opened it and as soon as it touched my lips, the thought entered my mind that I may be sucking Walter's big fat cock before the night was over. I was getting seriously horny just standing there.

I walked back to my sister's room and grabbed a pair of ankle socks with lacey-trim, then dug through her shoes. I tried on several pairs before choosing a simple pair of black and white tennis shoes.

After one last glance in the mirror, I was ready. It was pretty dark outside so I wouldn't have to wear a cover-up over to Walter's house. That first step out the front door was exhilarating. I had never been out in public, much less out of the front door dressed up before. My heart was pounding in my chest as I took the 37 steps to Walter's front door.

His house was lit up and I could hear the TV. Half of me wanted to run home, the other half of me, the naughty half raised my arm and rang the doorbell. As I waited those few moments on his doorstep, I nervously spun the lollipop on my tongue. My mind was running wild. What if he didn't like the way I looked? What if he came home, thought about it and was now repulsed by the idea of me dressing up? What if? What if? What if?

Just as I was about to run off, the door opened. There stood Walter smiling broadly as he appraised my outfit. "Mmmm, you outdid yourself Tommy. You look great!" I stood there dumbly twirling the lollipop in my mouth. He paused and looked into my eyes before saying that my name didn't really suit me now. I meekly replied that I liked the name Tonya. His smile broadened as he offered me his hand and welcomed me into his home.

Goosebumps popped up all over me as his hand rested on the bare skin on the small of my back, ushering me down the hallway. We passed the kitchen and continued on to the living room. This room was much smaller than my living room, one side opened to the kitchen, another had a closet and a hallway toward the bedrooms. The third wall was dominated by a big screen TV and its accessories. The forth wall had a single chair with an end table. A large, low table sat in about the middle of the room. The lack of seating sort of shocked me. I guessed I would be sitting on the floor.

When Walter offered me a drink, I readily accepted and followed him back to the kitchen. I checked him out as I followed, he was such a big man, I felt so small in his presence. He opened the refrigerator and withdrew two sodas, setting them on the counter near me. I leaned against the counter and watched him. He approached me and got really, really close while looking right in my eyes. I was terribly nervous, he was close enough that I had to stop twirling my lollipop, there wasn't enough room between us for my arm. Still staring at me, he reached around to open a cupboard and pull out two glasses, one in each hand. He set the glasses on the counter behind me on either side. Still holding the glasses in his hands, I was captured between him and the counter. My breathing got heavier and I felt myself flush being so close to him.

He leaned in even closer, I could feel his breath on my neck. My little cock was rock hard in my panties. I was beginning to panic when he whispered in my ear, "Damn, you're cute." He stepped in and slid his leg between mine, I spread them wide enough to give him space. I tilted my head as he took my earlobe between his lips. I melted. It felt like I was floating as this big man shifted his hands from the counter to my body and nibbled on my ear. One of his hands was on the upper most part of my butt, the other was sliding up and down my side, pausing as it passed over my chest and lightly pinching my nipple.

He pulled away from my ear, and while keeping close enough to my face that I could feel his warm breath on my skin, grazed my lips with his. I leaned toward him, and his lips met mine. The hand on my butt stayed there while the other slid up to the back of my head and pulled me in tight while his tongue invaded my mouth. Dropping my lollipop on the floor, I raised my arms and locked my hands behind his neck.

It was a loud, sloppy, hungry kiss. My knees were buckling and I was going crazy with desire. Without breaking the kiss, he spun us around so he was leaning against the counter. His hands were now on my butt, a cheek in each hand. As he kneeded my butt through my skirt, I began to grind myself against his leg. We broke the kiss and I gasped for air.

He asked very quietly, "Have you ever been with a man Tonya?"

Still out of breath and hornier than I had ever been before, I answered "Um, well, sort of."

"What does 'sort of' mean Tonya?" he inquired in the same whisper.

Grinding down hard onto his thigh, I gasped "I play with Derrick."

"How do you 'play' with Derrick? What sorts of naughty things have you two done?"

I leaned back in to kiss him, but he stopped me and pressed me to answer the question.

"He, um, I, well, his dick, I suck on his dick." I moaned.

"Does Derrick cum in your mouth?" he asked while still whispering. One of his hands slipped under my skirt and continued to squeeze my bare cheek. The other hand left my butt, slid around my body and slipped under my top. He rolled and pinched my nipples while I ground down hard onto his leg.

"Sometimes." I mumbled while glancing down at the huge bulge in his pants.

Raising his leg higher, causing me to push down even harder, "Sometimes? Where else does little Derrick cum?" The way he said 'Little Derrick' implied he didn't know who he was, but knew he was a young guy.

"Walter! Don't tease me! I'm going crazy here!" I squealed.

"Just answer the question Tonya, I'm almost done asking questions."

Now staring at his massive bulge, "It's embarrassing." He raised his leg even higher until I was on my tip-toes. "Okay, um, I like it, no wait, he, Derrick likes to cum on my face." Glancing up, I saw a big smile on his face. By this point I was sure my panties were soaked with my juice.

"Hmm, does Derrick ever suck on you?"

I moaned, "No, he doesn't like that. But he watches me, um, rub myself." Confessing all of these secrets, being dressed up for the first time in someone's presence and grinding on his leg was getting me so close. I felt a thin layer of perspiration on every inch of my skin. If I didn't slow down I was going to make a mess.

Both of his hands were back on my butt, under my skirt. "What do you 'rub' Tonya?"

"My... My dick." I groaned.

With a fatherly tone, he answered, "Tonya, little girls don't have 'dicks'. Little girls have 'clits'."

Hearing him speak to me in that tone, call me Tonya and refer to my dick as a 'clit' sent me over the edge. I squealed loudly and shook violently as my 'clit' erupted in my panties. He squeezed my butt tightly and pulled me up his thigh. I was twitching as my orgasm subsided, still loving the feel of his hands on my butt and his leg between mine. Walter leaned in close and kissed me gently.

After I had recovered, I slid down off his leg. I felt like a fool. I was so embarrassed. I came in panties! The proof was the wet streak down Walter's jeans. I always had these moments of doubt after I came, I judged what I had done in my horny state and was never pleased with myself. My skirt was pulled up around my waist and a huge wet spot left my panties in an almost transparent state. I tugged the skirt down to cover myself and beat myself up for even coming over here dressed as I was.

Walter broke the silence with a cheery voice, "Well, Tonya, I guess we should get cleaned up if we're still going to watch that movie." Motioning toward his pants and my lower body.

"Maybe I should just go." I uttered.

"Why on earth would you want to go? We were going to watch a movie, remember?"

Staring at the floor, I confessed "It's just that I feel so foolish. I mean what I did, and how I look. I stupid."

Wrapping his arms around me, he pulled me close and comforted me. I could feel his rigid cock through his jeans, it pressed in hard against my tummy. He told me there was nothing to feel foolish about. He told me I was beautiful just the way I was and how happy he was that I came over dressed up so pretty. After several minutes in his arms, I calmed down and agreed that we should clean ourselves up. We had a brief discussion about my panties and I decided I should run home, clean up, get a fresh pair of panties and I'd be right back. In the meantime he could clean himself up and get the movie ready.

On my way to the door, he stopped me, spun me around and kissed me deeply. He then asked, "Promise you'll be right back?" I nodded my head and smiled.

Upon entering my house, I ran to the bathroom and looked at myself in the mirror. A moist spot had appeared on my skirt and my top was all wrinkly. Crap! As I slid the sopping wet thong down my legs, my legs got covered in my cum. Crap! I quickly stripped and hopped into the shower. Careful to keep my hair and face dry, I washed myself off as fast as I could. My 'landing strip' was matted down and I was pretty much covered from the waist down. During this process, my thoughts were on Walter and what he had done to me, my 'clit' started to get hard again.

Jumping out of the shower I dried myself and dashed to Teri's room. I slipped on a pink silky thong, tucking my semi-hard 'clit' back again. Then to the closet to grab the little summer dress which was my second choice for an outfit earlier that night. The dress was white cotton with a flowery pattern. It was short, higher than mid-thigh. My favorite part of the dress was the spaghetti straps, for some reason I always found them to be extremely feminine. The white pumps topped off the outfit beautifully.

Back in the bathroom, I touched up my pigtails and lip gloss. I gave into desire and took the time to apply mascara and a flowery perfume. When everything was perfect, I almost skipped back over to Walters. On my way, I couldn't help but consider that this man was turning me into a horny little tramp! It wasn't a bad thing.

He greeted me at the door in denim shorts and a white t-shirt. That same massive bulge was squished into the shorts. I began to feel guilty, he had made me cum and I hadn't done a thing to help him. His muscular arms encircled me as soon as the door was shut. "You look better every time I see you Tonya." Looking up into his eyes, he lowered his head and kissed me. It wasn't as wet or loud as before, but still passionate enough to make my knees weak.

As we entered the living room, I saw a big bowl of popcorn and two sodas on the big table in the middle of the room. Walter dimmed the lights then took my hand and led me to the only chair. He sat down and pulled me onto his lap.

"Mmmm this is nice." He spoke softly.

I purred my response as I cuddled up against him, "Very nice."

With me on his lap, I could feel his stiff cock between my cheeks. I wiggled my butt a little, and heard him moan.

He reached for the remote and started the movie. He must have chosen a scene before I arrived, on the screen a pretty young girl was on her hands and knees while an older man sat behind her and played with her pussy with his fingers.

"Um, Walter, you do know that I'm not old enough to watch nasty movies like this, don't you?"

"Shhh, just watch the movie." was his response.

I leaned back and rested my head on his shoulder. His hands began to explore my body, they started on my hips and slowly made their way up my sides, across my chest and down to my tummy. They continued their exploration as I watched the movie. The man grabbed a dildo and began slipping it in and out of her dripping wet hole. His free hand was on her butt, rubbing circles around her little brown hole.

I could only picture myself in the girls place and Walter as the man. My little 'clit' was rock hard once again. Walters hands drifted down my thighs, past my dress then came back up under the thin material. Feeling his fingers trace lines all over my body took my state of horniness up a notch.

I sat up and grabbed my soda, my throat was so dry, I drank most of the glass. It tasted a little funny, but I didn't say anything. I learned later he had crushed up Viagra pills in it. Before I was able to lean back onto him, Walter reached up and slid the spaghetti straps of my dress off my shoulders and down my arms. I quivered with excitement when my dress fell into my lap.

Sitting squarely on his lap, I leaned back onto him and his big hands wandered over my hairless flesh finally finding my nipples which he massaged. My eyes couldn't help but focus on the big screen before me, the man had just withdrew the dildo from her pussy and was working it into her butt.

Walter's fingers were rhythmically squeezing my nipples when he whispered, "Have you ever done anything like that Tonya?"

"Had something in my butt?" I asked.

"Yes, have you ever had anything inside you?"

My breath was coming is gasps and that thin layer of perspiration had returned as I squeaked, "No."

"Little Derrick never put dick in you?" he asked.

A moan escaped my lips as one of his hands slid down and began fondling my 'clit' through my panties. My butt started grinding down on Walter's cock, it felt so good. "No, he never did." Knowing more questions would follow, I continued, "He likes my mouth. And.."

fantaseeboy
fantaseeboy
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