Peeping Tom

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"Hey big boy, you feel like finishing the trifecta?" I'm not a slouch, nor am I stupid, but I wasn't putting together what she was talking about.

"You came in my mouth. You came in my pussy. Do you feel like trying out the last hole?" I must have looked like an idiot. Anal sex was something that I had never tried. I had watched Paige with the butt plug in her ass last night, but the thought of putting my dick in there never crossed my mind.

"In a heartbeat, but I want you to know, I've never done it before."

Paige had a sly look on her face, "Me either with anything real. I've only had glass plugs up there, but you already knew that. Didn't you?"

Paige prepped everything. Large towel on the bed. The lube that I had planned on using when I jerked off for everyone tonight and her. Giving me the basics as far as instructions go, I was ready.

Placing my lubed head at the entrance of her ass, she pushed back, and I pushed forward. It took longer than I expected until the tip of my cock slowly disappeared up her bum.

As soon as it was in, I stopped pushing. Paige took over from there. Slowly she eased herself backward at a pace dictated by her. When I felt the cheeks of her ass come to rest on my skin, I knew that was it.

"OH FUCK. Don't move. So, fucking full. Oh, my god. So, fucking full." Paige leaned forward and buried her face into one of my pillows and screamed.

It was a completely different experience for me. It was hot and tight, but not the same as a pussy. I was on the fence, but it still felt great, and when Paige stared to move, it felt even better. The tight grip of her ass was like a vise around my shaft.

For fear of hurting her, I stayed as still as I possibly could while Paige moved back and forth, massaging her clit with her spare hand. Minutes of gentle action helped lower the safety net.

"Do it. Start fucking me. Just not too hard."

One hand on each side of her slender hips I did as requested of me. The momentum increased with each thrust. Paige grunted every time that I pushed forward but didn't complain once. It was something about the naughtiness of the whole thing that had cum inching out of my cock.

"Baby, I'm almost there."

"Me too." The movement and speed of her hand increased on her clit. "Fuck. Cum in my ass."

I remember cumming into her. I'm can't remember if she came or not. I know that it's selfish, but I was basking in my own glory and my mind was in another dimension.

Laying in a spoon position, I kissed Paige's shoulder and neck, while tracing my fingertips over her nipples. "You can stop that any time you want, because no matter how horny you make me, I'm not doing ass to mouth."

The thought hadn't even crossed my mind, but when she said the words, I have to admit that it sent a little jolt of electricity into my soft dick.

I woke before my new lover and took my time brushing my teeth and showering. Paige stepped in just as I was stepping out. It was a smooth morning transition.

Paige accepted my offer of coffee and some breakfast.

Making her an omelet, she stood on her tippy toes, wrapped her arms around me, kissed me and handed me an envelope.

"It was under the door."

"Guaranteed it's from your buddy Viv. Read it."

I finished buttering her toast and handed the plate to her.

I could see her eyes moving across the page, but no words were coming out of her mouth. "Aloud works better." Paige smiled and started over.

"Wow 812. That was amazing. Lots of compliments on your performance. You and my little minx from 722 make an excellent couple. So much so, that I think you should share an apartment. The action was hotter than most of what we've seen over the past few years. It makes me wish that I was privy to what you did after you closed the blinds. My place next Friday. We'll give everyone something to talk about. V."

"She said all that?"

"Everything but the part about us moving in together. I added that part all by myself." It was hard to get a read of her face to see if she was serious, but the tone of her voice led me to believe that she was.

"You said it yourself, rent here is expensive. I can move in here and we can split the rent in half. Or you move into my place. The rent for a one-bedroom is way cheaper."

"Okay. Where would I sleep in your one-bedroom apartment?"

"In my room silly. You came in me three times last night. Do you think that I'd make you sleep on the couch?"

"I don't..."

"Look, I get it. It sounds unconventional. We just met and aside from last night we don't really know shit about each other. I'm not Bohemian in the typical sense of the word, but I've never had solid roots or personal ties to anything or anyone. Something about you makes me want to change that. Enough so, that the idea of you and Viv together alone, pisses me off."

"Don't you have a lease?"

"They could rent my apartment tomorrow. Plus, they can increase the rate by six percent, so they'd be happy to see me go."

We never once lost eye contact during the long drawn out pause. Paige wasn't begging. It was more like she was presenting me with an opportunity. The pros of us living together were actually quite simple. She was beautiful. Sex with her was spectacular. We could split the rent and all the bills. And loneliness would be a thing of the past. The cons list was shorter, but it was still there. If she turned out to be crazy, I'd have to move out of my apartment.

The whole lion or mouse scenario played over again in my head. Take a chance and regret it later or don't take the chance and regret it forever.

"You pick the apartment. I'm just saying that mines bigger, in case you need some time away from me. If we share a bed, you need to sleep on the other side. You took mine last night."

Her squeals must have been heard down the hallway. She kicked her leg and shook her arms triumphantly. Jumping onto my lap, she kissed every inch of my face. "Baby, you'll never regret this. I promise."

Surprisingly, she was correct. There was a line-up of people just like me that were in line waiting for vacant apartments, and by Tuesday night Paige had a new address.

It didn't take long for us to hit our first bump in the road and that came on Thursday evening, gift wrapped in a manila envelope.

"Well Kyle, congrats on the new roommate. Very nicely done. I trust that it will not interfere with our liaison tomorrow evening. Apartment 926. Building "A". Please arrive no later than 9:30pm. V." 926. That would explain who was watching me and smoking a cigarette whenever I was out on my balcony. I couldn't see into her apartment, but she most certainly could see into mine.

The crossed arms, tapping foot and pouty face on my new roommate told me all that I needed to know. She was pissed off and it wasn't a secret.

"Look, I don't know why you're all revved up. I don't even know her, and I've never seen her. If you recall, you read the last letter to me. I didn't ask to go over to her place, nor did I say that I would. So, calm down a little bit. This is way beyond crazy."

Tears replaced the pouty face and the crossed arms moved up to cover her eyes. Getting on my knees in front of her I asked her what the problem was.

The tears were now accompanied by sobs.

"What? Tell me. You know that you can trust me." It took a few minutes for Paige to regain her composure, but it did come. Her words were sporadic between the sobs when she told me what was on her mind.

"She's old, but she's just so beautiful. She is elegant and sophisticated. She has lots of money and treats people poorly. For fun she chews up men and spits them out." There was a small bit of venom in Paige's voice as she told me about Viv, but there was something else that was bugging her.

"I never planned on going, so just tell me why you don't want me to go." This brought back the sobs and tears. Knowing I had to say something, I tried to ease the pain of what was hurting her.

"Paige, you are absolutely the most gorgeous woman that I've ever met in my life, and to think that you might even want to spend one single minute with me, makes me the happiest guy in the world. Maybe you can't see it, but you are elegant and sophisticated. Money, who needs money? We have each other." The money thing brought a smile to her face, but my next question brought back the gloom.

"Do you personally know any men that she's chewed up and spit out?" Paige nodded, but wouldn't look me in the eyes.

It turns out that when Paige moved into her building, she was accompanied by her boyfriend. He was a young blond haired, blued eyed, California guy and he caught Viv's eye immediately. Apparently, Viv used him the same way she used others, only this time she didn't let him leave. Paige's boyfriend stayed in the lap of luxury until Viv tired of him and tossed him to the curb. Four months had passed by, and neither of the women wanted nothing more to do with him. According to my roommate, this was a common occurrence.

That night in bed, I held Paige as tight as possible. I had a plan. It would take some persuading on my part to make it work, but I had to try something.

My list of things for Paige to do while I was at work was short and hopefully doable. Get a camera, with a long lens. Talk to someone in our building where we could be invited to watch Friday night's show. Trust me and pray.

I arrived home from work at the usual time. Opened a beer, eat supper, danced around the room with Paige and finally at 8:30pm made my way to the shower. Scrubbed clean, hair slicked back, a simple pair of khakis and a black t-shirt. At 9:15pm I kissed Paige and walked out the door.

Oli and Rob's apartment is on the tenth floor, 1026 to be exact. It is two floors up and two over from mine and the view of Viv's apartment couldn't have been any better. Like many others in this complex, they enjoyed some voyeuristic tendencies and liked to have mini parties to celebrate big events, and Viv doing a show, was a big event.

Viv opened her door wearing a sheer black negligee. The fine piece of silk showed lots of skin, while accentuating her body and blondish gray hair. She handed her new lover a drink and showed him around the room. The sexy older woman walked him over to the edge of her balcony, she was parading him around like he was the new prized stallion in her stable.

Moving him back inside, at the precise minute of 9:30pm, Viv lowered herself down and pulled out her soon to be lover's cock.

It was a show of epic proportions. Spitting, choking, slobbering, watery eyes and that was just for the blow job. When Viv's lover went down on her, her face contorted to an "O" as if she was instantly having an orgasm. Viv wanted to put on a good show, and what Viv wants, Viv gets.

The minutes passed with the face attached to Viv's snatch. When she made a spectacle of cumming, it was time to move on to the main event. Viv put herself down, hands and knees on a large ottoman in the center of the room. For her pleasure, she was facing the crowd that was watching her every move. Everyone across the courtyard was enjoying the show. Everyone but Paige.

To say that Viv over embellished the look on her face when her lovers cock sank into her, may have been a bit of an understatement. Her face was glowing with pride as her young lover thrust in and out of her with the kind of vigor and stamina that only someone in their twenties can possess. It had been a while since her last young cock, her last young lover, and she wanted to savor every second of it. Her only hope was that her audience was enjoying the show as much as she was enjoying putting it on. When the young penis erupted into her vagina, Viv knew then and there that this one would be a keeper.

Reaching down to Paige, I grabbed her free hand into my own, leaned forward and kissed her. The smile on her face could melt the coldest of hearts. With a "To us" toast, we clinked our glasses together and turned back to watch the show.

It wasn't all that hard to convince my younger brother to step in for me. When you live with your parents, you're twenty-three, play video games for a living, which is code for being unemployed, you really don't have a full agenda. So, the prospect of a couple of drinks, getting laid by a wealthy older woman and the fifty bucks that I gave him in the lobby when we swapped clothes, was more than enough to pique his interest.

My younger brother didn't have to know all of the details, but our resemblance is close enough to pass and we have the exact same build, so that was a plus right from the start.

For the first time since moving into this building, Paige and I kept our blinds and drapes closed tight on an almost permanent basis.

My little brother lasted for just under six months living with Viv. He was super excited that he walked away with $25,000 as a performance bonus. It turns out that it was he who tired of her, and not the other way around. Go figure.

Viv did send Paige and I a nice little thank-you note, along with a check for the sum of $50,000 enclosed in it. She said that she was moving back home to Europe where her way of life was more widely accepted, and she wanted to make amends for any past wrong doings before she departed.

As for Paige and myself, we haven't changed our exhibitionist ways, we just changed how we do things. We no longer share nudity with our neighbors, instead we have sex in public places, flash unsuspecting passerby's and send nude photos to random cell phone numbers.

Life is good!

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6 Comments
GoosebumpgiverGoosebumpgiverabout 2 years ago

Loved every minute of it.

Albany ChrisAlbany Chrisalmost 3 years ago

I really like the first two thirds, the organized voyeur shows was a great idea, but the last third didn't interest me much. It was a nice twist but I wasn't invested in the characters enough to care that much. Thanks!

ffajazffajazabout 3 years ago
about review by Anon: Nice premise

Sounds like they want to tell you how to write YOUR story, if they are so great should write there own story and leave there name and not be using the Anon name. And if the story was as bad as they say why did it rate so high? Anon is a jerk

AnonymousAnonymousover 3 years ago
Nice premise

But the sex -- even though it was plentiful -- was generally not erotic.

Not enough dialog about what either wants from the other, whether it should be faster, slower, harder, etc. Nothing really about how his cock felt in her hand, her mouth, her pussy or her ass. Nothing about how her breasts felt, tasted, etc. What were the nipples like? Did she like them licked or sucked better? Did she want harder or softer tweaking, sucking, etc.

Could have been much better.

eibirbeibirbalmost 4 years ago

Good story with a nice twist at the end. Well done

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