Always Watching...

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Longtime girlfriend cheats on boyfriend, pays the price.
13k words
4.31
144.7k
20

Part 1 of the 3 part series

Updated 09/27/2022
Created 03/27/2006
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It was around 1am when Jenny got home from a night on the town with her friends. Lately, she had been going out with them several times a week--more and more frequently by the week it seemed. We had been dating for over seven years and she had moved into my apartment about four years before. The only thing we lacked was the marriage certificate.

She had just graduated from college with a degree in business and was working at a local firm doing marketing work. She had grown up in this small town and if she didn't know someone in it, her family did. That was how she got her job, family connections. As with all southern towns, this one was just as sleepy with a very well-nourished "grape-vine." Everyone went to church. Some for the right reasons, most to help their image which translated to people doing business with them.

I was a car salesman over in the next county. I too went to college but couldn't settle on anything I really enjoyed. So I decided to sell cars. During my college career, I was involved in a fraternity. I had made a lot of connections during my time in the fraternity and made sure to keep them close.

I was sitting in my favorite recliner, watching television, quickly falling asleep.

"Hey baby," she said walking over to me, leaning forward to kiss me gently on the forehead, "I believe it is time for you to go to bed."

Though she and I had been dating for as long as we had, there was something about her that still drove me crazy. The only light in the room was from the television, but that was all I needed to be able to see how beautiful she was.

Jenny has straight, shoulder length dirty-blonde hair and blue eyes. She is 25 years old, stands at around 5'6, and weighs around 165. She is terribly self-conscious of her weight. Her arms, legs, and ass are a little chunkier than she would have liked, but I liked them just fine. Her breasts were 34B, another point of contention for her. She made a big deal out of the fact that she had too much "meat," as she would say, in the legs and ass, but her breasts were small--definitely backwards of the way she would have liked it. She definitely had a "ghetto ass." When she wore blue jeans, her thighs and ass looked great.

But again no matter what she thought of her body, I thought very differently. After she awoke me from my little snooze with a kiss to my forehead, she moved back to the bedroom to change. I rounded the corner just in time to see her take off her white, button down blouse and toss it on the bed, leaving her in a white, full-cupped bra, and black dress pants. The black pants hugged her ass and legs, making my hard-on grow even harder.

One of the things I really enjoy is to video tape Jenny and I having sex, and then a few days later watch it. I definitely get my rocks off watching her perform on camera without her having any clue that she was on video--I'm just fucked up that way I guess. Our bedroom, the living room, and the bathroom all have video cameras hidden in various places--complete with sound, and planning to put cameras in the other rooms! All I had to do was go over to the computer in my bedroom, set the timer for when I wanted them to begin recording, or I could simply start the recording immediately if I chose, and I also had a feature that allowed them to be activated by motion. If I knew one of Jenny's friends was going to be over at the apartment that day, I would make damn sure the motion sensor was activated. I had bought and installed the video equipped two years before. Of course when I say "video tape," I don't actually mean video tape--everything is recorded onto the computer and then I can determine what to burn to a DVD for further use! I had a program on the computer that allows me to "cut and splice" the videos anyway I like. I was proud of my handiwork and it had come in great use on several occasions.

One such occasion was when Jenny's good friend Cassie came for a visit. She spent two nights with us. There is only one bathroom in the apartment.

Cassie is 24 years old, around 5'6, 125 pounds, black shoulder length hair that she liked to wear up a lot, and I would guess her tits to be in the 32C range.

She keeps her pussy very well-groomed, though not totally shaven. She also likes to frig herself in the shower—which I found to be very interesting.

But I digress. The computer in our bedroom is just to the left of the bedroom door. Our bed was immediately across the room from the door, and the bathroom door was just to the right of that. After Jenny had taken off her blouse, she immediately entered the bathroom and closed the door. I quickly clicked the computer mouse waking the machine from its slumber and hurriedly opened the program that controlled the cameras. I turned them on for both the bathroom and bedroom.

The cameras came on and immediately I was watching my girlfriend sitting on the pot taking a piss, with her black pants, and black thong panties pushed to her knees. The camera I was using (there were others in the bathroom) was positioned just below the small window which was directly across from the commode--this resulted in the angle of the camera shot to be around a 45 degrees. The window was smaller than an average window and higher up than usual. I had put an old football picture below the window around the time I put in the cameras--a great cover. If the person on the commode was sitting upright (as opposed to slumped over for some fucked up reason), and if the top she was wearing showed any cleavage at all, I could usually get a pretty good view!

For the most part, Jenny is a modest person. She isn't a big partier and I have never, ever gotten her to agree to a threesome or any other act that would involve other people. In fact she usually gets pissed when I bring it up, so I don't usually. But she does understand that I have fantasies, so there are some that she does participate in. One such fantasy is that I have full control over her. If I tell her to do something that isn't way over the line, then she does it. For instance if I were to tell her to jump off our third story apartment deck, of course she wouldn't do that. But if she's cooking or watching television or anything else that isn't life-threatening, and I tell her to strip and suck my dick, she does. I used to really like fucking her in the ass. Don't get me wrong, I still like it, but since she's started to like it more, it has lost its luster a little! So that was one of my little fantasies--but not so much anymore. Another fantasy that she goes along with is telling me stories while we fuck. She doesn't do this all the time, but I do enjoy hearing her telling a story that she HATES to think about--like fucking her best friend and liking it. She has had to tell me a whole lot of stories that she thinks up without any help from me--and I do a good job of making it known when she's thought of a good one!

I watched Jenny pull up her panties and pants after flushing. She washed her hands and then opened the bathroom door. She took one step into the bedroom before she noticed me standing at the foot of the bed.

"Did you have fun tonight?" I asked.

"Yes, we stayed out a little later than I thought we were going to though," she said tiredly.

"Yeah, I noticed," I said stripping my blue jeans off, "drop your pants and panties to your ankles and lean over the bed."

She didn't say a word. The button on her pants was on her left side as was the zipper--she quickly took care of both of them before "shimming" the black pants down her thighs before they fell to the floor--she was dressed in nothing but a bra and black thongs.

She quickly slid the thongs down, dropping them on top of her black pants which were now bunched up around her ankles. Her pussy was completely shaven. Her lips were small and didn't puff up very much even when aroused. But they did open up when aroused, much like a flower. In a standing position (legs together), you can just barely see the top of her slit before it disappears between her legs. Even when she's standing in a normal position, just a little of her slit is visible.

"Remain standing for a minute," I said as I looked at her naked ass and legs from behind. I knew she was self-conscious of both of those areas more than any others on her body. Her ass wasn't large but it was definitely overweight. She didn't have the hourglass shape women try to accomplish--she had more of a pear shape to her. She had simply studied too much in college and didn't work out enough. Her thighs were much the same. According to her, if your thighs touch they are too large. They definitely touched, but it wasn't like she had fat rolls or anything like that--a couple of months of working out would have her back down to a normal body weight.

On top of the whole "touching" problem, she had a slight problem with cellulite. When standing straight up, she had areas on both thighs and ass cheeks that were slightly "dimpled" if you want to call it that. If you were to ask me, it really isn't that bad, but according to her it was horrible. Then there is the issue with her calf muscles. They too are wider than "Hollywoodperfect." But again I liked them. However, it doesn't matter how much I liked something on her body, if SHE doesn't think it's up to par, then there was nothing I was going to be able to do or say to change that. So when I stand her upright and simply stare at her naked backside, she hates it!

"Joe, you know I don't like you looking at me like that," she protested after only a couple of seconds.

"Okay, then I'll stop. But you will ask me to whip you for being out all night without calling home to let me know you were okay or you can ask me to please stare at your beautiful butt and legs. And you will ask me to let you move over to the full length mirror so you can look for yourself," I replied smugly. I knew full-well that she didn't want to do either one.

"Joe, that's not fair!" She again protested, "I was out with four friends. We didn't have any problems."

"And I am really happy that you didn't! But the point remains that you weren't considerate enough to just call and let me know you were okay and that you would be home late!" I replied immediately, "So what's it going to be?"

"You are not going to whip me Joe! I'm not a little girl and you're not my daddy!" she replied now pissed off.

"Is that right?" I responded now getting a little angry, "Then not only are you going to go ahead and finished taking off your pants and panties, you are also going to take off your bra, move over in front of that mirror, bend over and ask me to whip you for back talking me! Then you are going to apologize!"

"Alright, Joe, I'm sorry. I apologize for not calling and I'm sorry for not asking to look at myself in the mirror," she said backing down.

"It's too late Jenny. If I let you get away with this shit this time, you'll be more likely to do it again."

She dropped her head as she stepped out of her pants and panties, knowing that she wasn't going to win the argument. She reached behind her to unhook the bra allowing it to slide down her arms and to the floor, baring her to me completely for the first time tonight. As I said earlier, she had size 34B tits. When she isn't aroused, it's almost as if she doesn't have nipples, just two cone-shaped, seemingly tanned areoles. She doesn't have much of a tan, though she isn't snow white. When aroused it's like she has no areoles at all—just two eraser like nipples.

She walked slowly over to the mirror. It was a see through mirror. Though it was against a wall, on the other side of it I had a camera that would be recording everything!

She stood facing the mirror for a second, giving herself a once-over. She had a 'pouty,' "I know I'm in trouble" look on her face, much like a little girl would have before getting a spanking. She turned around with her back to the mirror. Knowing what I wanted, she turned her body slightly to allow her to look at her naked back, ass, and legs.

"Grab your ankles," I ordered picking up my 1 1/2 inch leather belt. I watched in the mirror as the muscles in her ass and legs tightened as she bent forward to do as she was told--the cellulite totally disappearing.

"I want you to pull your ass cheeks apart as far as they'll go so I can see your asshole and pussy," I continued. She did as she was told without hesitation, "Look in the mirror."

She turned her head to watch as I placed my hand on top of her ass and slowly stroked downward, squeezing her ass along the way.

"How many licks do you think you deserve?" I asked drawing out the process, continuing to rub down her ass crack to her open pussy. I looked at her pussy and could tell that she had been recently fucked. After a good hard fuck, the outer folds (the Labia Majora for you medical buffs)of her pussy remain wide open (totally exposing her labia minora) and her labia minora remains open almost in a spherical form—or in the shape of the dick that has just fucked her for a better, more graphic description. It didn't gap open, but they were certainly apart and very obvious.

Without letting on that I noticed anything, I continued to slide my hand down her asshole and to her pussy, pushing three fingers in without any problem. I knew immediately that she had been fucked—her pussy was full of cum, making it very easy to slide my fingers in-and-out.

"How many licks?!?" I asked more forcefully, still not letting on that I noticed anything.

"Aaaa uhmmmm," her face was turning red from being bent over for so long and from having to hold her ass checks apart, "Ten."

"Ten? That's all? Are you sure?" I asked.

"Yes," she replied worried that I may decide on more.

"Fine. Grab your ankles again," I said agreeing, bringing the belt up and landing it across her ass cheeks before she was all the way down, startling her.

"Ouch!" she jumped up.

"That doesn't count," I said putting my hand on the small of her back to push her back down. I landed the belt just under the first spot and continued to paint a red "picture" down her ass cheeks and onto the tops of her thighs before reaching the tenth lick, "Go get the KY jelly and get your asshole ready for me."

I wasn't going to fuck her pussy. I didn't know who she had been fucking and I wasn't real interested in sloppy seconds even if I had known. She immediately did as she was told, going into the bathroom to get the KY out of the medicine cabinet.

I stripped off my boxer-briefs finally freeing my raging hard-on. She re-entered the bedroom with the KY, opening the lid. She stood by the bed as she dipped two fingers into it, hiked her leg up slightly, and began to apply the lubricant to her asshole.

"Smile. Act like you want to do this," I reminded her. Even though she likes taking it up the ass, she definitely wasn't in the mood right now, after having been out late, the fucking she got earlier, and the ass whipping she just got.

To her credit, she played her role. She knew if it wasn't good enough that I would probably give her another spanking. So to avoid that, she cooperated fully.

After she was finished lubing herself, I walked up to her to allow her to do the same to me. She dipped more KY out before slowly stroking the entire length of my dick. Reaching around her to pull her towards me more, I leaned down giving her a gentle kiss.

After I was lubed up enough for her liking, I grabbed a towel from the bathroom to allow her to wipe her hands off with before ordering her to get on the bed on her hands and knees. Once she was on the bed, I climbed in behind her.

"I want you to remain propped up on your hands the entire time, understand?" I didn't want her to put her chest on the bed and put her head in her arms like she does sometimes. I had a camera in the picture that was hanging on the wall at the head of the bed. If she remained propped up, I would get a good picture of her face as I fucked the hell out of her ass. Though her tits are only B cups, they would still make a great show for the camera as they bounced around.

I pushed her knees slightly further apart than straight under her which lined her up nicely with my dick. Even though she had started enjoying getting ass fucked, she didn't enjoy it really hard.

Without the slightest hesitation, I grabbed her hips, and pushed forward, burying my 8 inch cock balls deep in her asshole.

"Holy shit Joe!" she said loudly turning her head, grimacing. I held myself in for a few seconds before I backed out and used her hips for leverage again to plow forward, "That hurts! Go slower!"

"Look forward and act like you like it. If you don't, you're going to get another ass whipping," I responded.

Normally, she would have put up a little more of a protest. But, as she did when I was getting ready to whip her, she did as she was told immediately--guilty conscience maybe?

I continued to pound away at her ass and a few minutes later she was begging for it.

"Come on Joe, harder! Please fuck me in my ass, hard!" she cried out.

She was doing a really convincing job. I didn't know if she liked it or not, but she sure acted like she did and the cameras were catching all of it!

I watched her ass cheeks as they jiggled violently from the pounding her ass was receiving. I always like watching her ass cheeks. I have told her before that I liked it, but she just uses that to prove that she's fat.

After five good minutes of hard fucking, I slowed down a little. I ran my hand down to her pussy and began fingering it. She was soaking wet and I knew it wouldn't take much to get her off.

"Tell me a story," I said as I began playing with her clit.

"What kind of story?" she asked.

"I want you to surprise me," I said slowly stroking in and out of her asshole.

After a few minutes of silence, she began, "Well, last night, I was out with several of my friends. Around 10 or so, Amber and I went to her house. The others had to go home. We were both a little tipsy, but definitely not drunk," I increased my attention to her clit causing her to push back against me. When she starts pushing back, there's no doubt she likes whatever it is I am doing to her.

Amber Stiles is one of Jenny's most beautiful friends. I dream about fucking her all the time. She was had a slightly darker complexion—like a full-time tanning bed tan. At 23, 5'5, 115, her mid-back black hair, black eyes, and 30B (just guessing) tits were more than I could handle! As soon as Jenny mentioned Amber, I started fucking Jenny harder.

"Amber was wearing a white undershirt with a long sleeved, stripped, button down collared shirt, and black pants. She left the button down shirt completely unbuttoned, allowing the undershirt to show off the tops of her breasts really nicely," Jenny continued, "We mixed some daiquiris with a generous amount of vodka. While I was mixing my third one, she came up to me and without warning kissed me on the lips."

"I think you're beautiful," Amber said.

"Ah, thanks, Amber," Jenny said shocked, "Amber leaned in to kiss me again, this time I responded by kissing her back.

Jenny continued telling the story, "Amber and I kept kissing while she unbuttoned my blouse and before I knew it she had taken it off. At first I was repulsed that one of my best friends was taking my clothes off. But then she unbuttoned and unzipped my pants and immediately pushed her hand down my panties and palmed my pussy."

"Take off your clothes Jenny," Amber whispered softly in my ear.

"It was like I was hypnotized," Jenny continued, "I unhooked my bra and pushed my pants and panties down and off, leaving me completely naked in front of my best friend, who was still completely dressed."

I had steadily been playing with Jenny's clit during the entire story but when she got to the part about Amber palming her pussy, I squeezed her clit a little harder than normal. This caused Jenny to totally begin fucking me back, ramming my cock up her ass as far as it would go.

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