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Peeping Tommy
Peeping Tommy
by Miss Anonna

I had lived in my new house for approximately four months now and on this particular day I noticed a car in the neighbor's driveway that I had never seen before. Several times I found myself peering out of the window to check out who may be over there as I had met the neighbors before but didn't get much info on their social lives. I remember being nosey and upset at myself for it but I was dying to find out if one or the other was cheating.

Somewhere around the evening I peeked again out the front and saw a young man heading to the car in question and I quickly made the assumption that Jaynee was having an affair but the young man opened the trunk and removed some luggage. Confused for a moment, it struck me. I did remember them talking about a son in college and had to take a second look because this kid was well built.

I sat at the kitchen table for a few minutes watching him and then decided to go out and get the mail, timing it so that I would be out there when he came back to the trunk. I had my tightest sweat pants on and a spaghetti strap tee that was also tight enough to show my hardened nipples and I have to say for a forty year old woman, I was looking damn hot. I tossed on a running jacket to cover my nipples because that would have just been playing unfair and I didn't want the Jaynee and Ted to think I was out "cougaring" their son.

I laughed to myself and headed out the front door and down the driveway to the mailbox where I opened it and looked in. I fumbled through a few pieces of mail and watched him come out of the house. He stopped quick as I pretended to look at my mail but I was watching him off the top of my glasses, even twisting my head slightly to make it look like he was walking on top of my glasses frame. He was definitely built nicely. His strong shoulders and neck protruded from a muscle shirt that wasn't long enough to reach his waist and allowed a sweet tuft of hair along his belly that I sure wanted to find where it ended.

I shook the thought out of my head as I quickly realized the tryst in my mind was out of the question but it sure was an interesting fantasy. He smiled real big at me and waved frantically in the air.

"Hi!" He yelled. I looked disinterested but smiled.

"Hello!" I yelled to him waving a piece of mail and then I lightened up, smiling a little brighter. "You must be Jaynee's son." He nodded. "Are you home from college?" I hesitated, "for the holidays?" He shut the trunk of his car, twirled around and headed toward me. I raised an eyebrow to myself and bit my lower lip.

"Yes," he said stepping over the curb and onto the sidewalk. "All done for this semester and I only have one more to go." He said very confidently as if he were either trying to impress me or giving up his age. I looked down at a piece of mail in my hand and then again studied him over the rim of my glasses.

"Nice." I said smiling and thinking that word had nothing to do with our conversation but everything to do with his body. "What are you taking?" I said knowing full well he must get that question every day of his life.

"Physical therapy," he said excited. "Isn't that what you do?" He held out his hand as he approached me. I was taken aback slightly knowing he knows something about me. "I'm Tom, by the way." I took his hand and lightly shook it while he squeezed mine like a melon. I wondered what that would feel like on my breast and for a moment thought how nice it would be of me to teach him some massage techniques. I nodded and tossed my naughty thoughts aside.

"I'm Anna, Tom." I said. "But you can call Miss Guided." I noticed his eyes fell to my chest and I tugged my jacket to cover up what could be an embarrassing moment for him but my jacket would not slide past my taught nipple. It's funny how things can change so quickly.

"It's a pleasure to meet you, Miss Guided." Tom said so directly that I chuckled and didn't have the nerve to correct him. I had thought maybe somewhere in the future he would figure out what I really meant.

"It's nice to meet you, too, Tom." I said and let go of his hand. "So who's been talking about me? Did your parents tell you I was a therapist?" He began to nod.

"Yes," he said. "My mother said that I should talk to you about your career and job experiences some day and maybe you could give me some tips or something." I smiled humbly at him.

"It would be nice to know what they teach you today," I said. "But honestly, I left the practice and spent a few years in Tibet, learning more holistic approaches in massage and mind." He looked at me strangely and then raised his eyebrows. "Stop in sometime this weekend and we can chat." I said but wanted to recant, knowing full well that I was putting that boy and my relationship with the neighbors in grave danger. I smiled at him and winked.

"I would love that!" He said with his eyes wide open and a sweet, child-like grin. I headed back into the house after watching him back away, and then turn toward his house. He may not have known it but he had a boner and it was obvious to me.

Several hours later it was dark out and after a shower I went around the house turning out lights. The last light I turned out was my office and as I was drawing the shades, I saw someone outside of my house. Peering into the window and out into the dark it looked like Tom. He knelt down and then wandered over toward his house but I felt like he had been looking into my house. I pulled my robe shut as I had been roaming the dwelling without giving my nudity a thought.

I quickly turned the desk lamp on and leaned over the desk, glaring at the computer. My computer had security camera feeds on it and I watched the one just under my office window and saw Tom peering up with widened eyes. I thought that maybe he was looking into my window but the thought made me excited rather than angry. I grabbed the duster that was on the chair, turned around and began to dust my window shades, reaching up as high as I could while looking down into my yard to see if I could spot him and I did.

I could feel my robe coming undone and reached to catch it but decided just to let it fall open, exposing my perky breasts but the window sill covered me from mid hip down. I danced around a bit with the duster and then turned around to view the camera feed and sure enough he was straining his neck just to look in. I walked past the window several times, watching him watch me and was beginning to enjoy the game. I tried to look closely at the image on the computer but I couldn't tell if he was masturbating or not. Secretly I wanted him to be wanking in my yard and the thought of it made me wet.

I knew I had to put an end to this charade so I ran down to the basement where I have concrete stairs that go up into the back yard. When I got to the door, I didn't want to spook him so I opened the door slowly and tipped toed up the stairs. I peeked around the corner into my side yard and saw Tommy sitting against his house. I adjusted my eyes to the dark because it looked like he was holding his crotch and then I saw his hand come out from beneath his sweats. I cupped my mouth and waited a moment.

"Tommy!" I whispered loudly and watched him look around. He got up and started to walk toward the back of his house. "Tommy!" I whispered again. "Come here." He finally saw me and looked all around him like he confused but soon began to walk toward me. I could faintly see him attempting to hide his erection.

"Yes, Miss Guided?" He said and I almost laughed out loud.

"What are you doing out here?" I asked and almost gave him a good excuse but he was able to come up with one on his own. I held my robe together with one hand and held onto the wall with the other, peering around the corner.

"I uh," he started. "I thought I heard someone out here and thought I would come check it out." He started to look around like he was concerned. "My parents are out tonight and I don't really know the neighborhood."

"I thought I heard someone, too." I said slightly louder than a whisper. "Did you see someone?" I said knowing full well the only person I saw around was him, looking in my window. "Maybe I should lock my doors or maybe we should call the police." I said frantically, pretending to be scared. He put his hands out to calm me down and got a real serious look on his face.

"I don't think we should jump to conclusions just yet." He said. "Don't worry, Miss Guided. I will protect us both if it comes to that." He continued to look around as if he were a detective. I sat down on the top step and looked up at him.

"Did you here that?" I said, knowing the forest behind us was full of wild animals, but I was enjoying the game and his dick was right in front of me as he scanned the back yard like a warrior. I could tell he was a nervous though; however I wasn't sure if he was skittish about the noises or the hot older lady next to him considering I caught him many times looking directly down into my robe that barley covered my breasts at times.

"I heard something." He said. "But I don't know what it was." He turned toward his house and I could tell he was adjusting his excited tool. When he turned back toward me I noticed he hadn't really hidden himself very well or he was trying to give me a hint. Though it was dark out, his light grey sweat pants gave away his position in so many ways. Tom knelt down next to me and whispered.

"Have you ever had trouble in this neighborhood before?" He asked and I nodded negatively. "I doubt we have anything to worry about, then." He said and rested his hand on my shoulder lightly massaging me. His movement was causing my robe to open up at the top and the material brushing against my nipple was invigorating. I slowly stood up and looked around. I expected him to follow my lead but he remained seated on the top step so I grabbed the corner of the house and peered into the side yard, practically burying his head under my robe. Had it been light outside he would have seen everything under my robe as clear as a bright sunny day.

"Oh, Sorry." I said chuckling. "I didn't mean to ..."

"That's quite alright." He said with eyes wide open. "Do you see anything?"

"Just some guy running up the street," I said.

"What?" Tom grunted and then stood up so fast that his erection bounced against my hand. He bolted behind me to look around the corner. I chuckled.

"I'm just kidding, Tom." I said. "Relax." He was up against me and I could feel his excitement between my ass cheeks. Within seconds I could feel my vagina welling up with a waterfall of pleasure. I pushed my ass into him but he didn't back away. I felt him take a deep breath and then slowly back off of me. "I think we are being a little too paranoid, don't you think?" I said bending a little further over and trying to find his stiff cock again with my ass.

I reached behind me and found his hip with my hand. Pushing him slightly out of the way I could feel the head of his cock in the palm of my hand. He moved with the ease of a gentleman and allowed me to slip out of the precarious position I was in but secretly I had hoped he had stood his ground. I sat back down on the top step.

"You're right." He said with his head down. "Maybe we are being a little crazy but what if there is someone out there prowling around? Maybe I should hang around for bit just to be sure." I looked up at him and then dropped my head to see his crotch right at eye level. Tom was no doubt hard as a rock and I stared directly at his dick.

"I'm OK with that." I said slowly. "I enjoy your company and I don't want to see either of us getting hurt." I looked back up at him and a brief moment passed before he spoke.

"I, uh," he started. "I think you are awesome and I, uh... I will make sure nothing happens to you, trust me." He said gaining more and more confidence as he spoke. I reached out to him and put my hand on his hip, nonchalantly folding my thumb over the head of his cock.

"You're a sweet boy, Tommy." I said. "Thank you." I slowly let my hand slide down the front of his leg pulling his cock down with my thumb and I knew right then this night was not going to end without me having the neighbor's son for dinner. I watched him as he swallowed hard when I got up on my knees, using his leg to pull me up. I pushed out my chest while staring directly at his erection, paused for a moment and then looked up at him. He seemed to be scanning the yard with his eyes and then he looked down at me.

"What are you thinking?" I said in a manner that could be construed as either a tease or a worry. I watched him swallow hard again. I raised my hand up to him in a gesture to help me up and he grabbed the back of my elbow and brought me to my feet. His strength felt good.

"I'm not sure what I'm thinking or I'm not sure that what I'm thinking is right." He said and then shook his head. "It doesn't matter, I think we are safe and we can relax." I pulled my robe tight with both hands causing it to hike up my butt and then I turned to peer around the corner of the house again. I gasped.

"What is that?" I said with conviction and felt him move closer to me. I tugged harder at my robe and hiked it up even further.

"What is what?" He said as his chin appeared over my shoulder. I felt him right up against me but not pushing into me.

"That," I said. "Next to the house across the street?" I felt him get even closer and his hard cock was once again pressing against my ass. "Do you see it?" I asked. He grunted and I raised myself up on my tip toes, leaning further around the corner. As he leaned further into me I felt his sweat pants rubbing against my lips. I took a deep breath.

I reached between my legs and felt around for the waist band of his sweat pants. I pushed my finger and thumb between his sweats and his skin and pulled outward. I felt the head of his cock brush my finger and slowly pulled it forward. Lowering myself slightly I rested the head of his cock on my swollen, wet lips and before I could complete my task I felt him lurch forward and I fell off my tips toes.

"Oh, my God!" He cried and began to back up. I quickly reached around him and grabbed his ass, pulling him back into me.

"Shhh," I hushed at him and he came forward again thrusting his whole cock into me. My eyes widened and I took another deep breath and let it out, almost painfully. His hands wrapped around my waist and his chest fell onto my back. He began to pull his cock out of me but again I pulled him back into me.

"Miss Guided," he whispered in my ear. "What are you doing?"

"It's OK, Tommy." I said grabbing his hand and pushing it into my robe and over my breast. "I'm helping you with your frustrations and you're helping me with mine." I grabbed the back of his neck and pulled his head into my neck. His hands began to desperately explore my tummy and breasts and then he began to slowly thrust his cock in and out of me until I grabbed his hands and led them down to my clitoris. I helped him push against my little button until I couldn't take it anymore. I felt a surge of warm energy travel through me and I felt the flow from my lips. I began to breathe heavy and reached under him, grabbing his testicles and pulling him deep inside me.

I felt his fingers dig into my neck and I felt his cock pulsating in my fingers so I pulled myself off of him, spun around and knelt down. I didn't even get a chance to wrap my fingers around him before my face was washed with his semen. I grabbed his testicles and wrapped my lips around his throbbing tool. He quickly jerked back and shot another round into my mouth.

I wrapped my hand around the base and squeezed the last little bit out of the tip of his dick and waited for him to stop quivering. I lightly kissed his cock just under the head and ran my tongue up the shaft. I stood up and put my hands on his neck.

"It's OK, Tommy." I said. "I think we're safe now." He smiled and shook his head.
Submitted by:
MissAnonna

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