Always Watching... Ch. 02

I helped Amy put the dildo on and helped her onto the bed.

"Jenny," Amy began, remembering what I told her to say from a while ago, "Ask me to fuck her asshole. Remember to say it like you really want it and smile!"

As I said before, Jenny likes it in the ass as long as it isn't really hard, and as long as it is from behind. She hates taking it when lying on her back. With her legs bent back as far as they were, the dildo would go a lot farther than what she was accustomed to taking.

"Amy, please fuck my asshole," Jenny said as seductively as she could in the position she was in. She smiled beautifully. I lubed the dildo up with KY and then helped Amy align the head of it with the entrance to Jenny's asshole. She pushed forward, impaling her friend's now well-used asshole on the phallus.

"Oh god!" Jenny cried as Amy continued to slide it deeper. When she had the phallus all the way in, she laid down on top of Jenny and slowly began fucking her. She turned Jenny's face, kissing her hard on the lips before moving her head down to suck on Jenny's rock hard nipples. Amy continued fucking Jenny's ass for several minutes.

I climbed up behind Amy and sank my rock hard cock into her awaiting pussy. I used Amy's body to impale the dildo into Jenny. Amy no longer had control as I fucked her pussy, which in turn drove the dildo hard and deep into Jenny's ass.

"Oh shit!" Jenny sighed.

"Oh Joe," Amy said now sucking on Jenny's tits furiously, "That feels so good."

We continued like this for a few minutes until I decided to do one more thing. I pulled out of Amy and helped her off the bed. Jenny remained cuffed to the headboard, her asshole remained the size of the width of the dildo that Amy and I had just been ramming into her.

I released her from the restraints and began massaging her muscles to help get the blood flow back. She was sore all over! Then, with the dildo still attached, I had Amy lie down on her back. I had Jenny get on top of Amy and sink her pussy onto the phallus. This was a nice change for Jenny, thankful the dildo was now in her pussy.

I climbed behind Jenny, spread her ass cheeks, and because it still had plenty of KY Jelly from the dildo, I easily sank my cock into her backdoor. Because of the dildo, it was still relatively tight. I reached around her with both hands, grabbing both tits, using them as leverage to slam my cock as deep into her bowels as I could. The feeling of the dildo going in and out of her pussy drove me towards an orgasm. Jenny had never been so filled. She fucked herself on both phalluses as best she could, bringing herself to another orgasm.

I immediately pulled out of her once she came. Both girls were exhausted. I had Jenny lie next to Amy. I had Amy give the strap-on to Jenny, who put it on. Amy knew what was coming, straddling Jenny's legs to sink her tight pussy onto a dildo for the first time in her life. I got behind Amy and pushed her forward, exposing her brown hole to me. As Jenny fucked her, I put a little more KY on my cock since Amy was totally dry. I then aimed my head at her tiny puckered hole and slammed forward.

"Oh shit!" she cried out loud, "I am so filled! I don't know how to explain it!"

She began babbling something. I could make out 'damn' and 'fuck' and 'harder,' but not much else. It wasn't very long before Amy came in a crashing orgasm that had her pushing her arms under Jenny's back and head, squeezing her tightly, forcing Jenny into her enormous chest. I could heard Jenny begging to be let go but Amy didn't let up for a few moments.

Eventually Amy released her, calming down. With the dildo still in her, I continued to fuck her ass, reaching around to roughly squeeze her huge tits.

"Tell me to cum in your ass again!" I demanded, now sweating furiously from exertion.

"Joe, cum in my ass again! Please!" she begged. Squeezing as much of her breasts as hard as I could, I slammed my cock home one more time, sending my searing hot cum deep into her ass.

I pulled out with a plop and sat at the edge of the bed. Jenny was nearly asleep. Amy was breathing heavily.

"Jenny, are you still awake?" I asked.

"Yes," she said quietly.

"You and Amy go take a shower. I'll be in there in a minute," I replied, "I want you to bathe Amy and she bathe you. When I get in there, I want you both to bathe me. When lovers bathe, they make out and rub on each other. I know you two are tired, but don't forget to play around. Do you two understand?"

"Yes," Jenny replied leading Amy down the hall and into the bathroom. I heard the water begin running and the door close. I walked tiredly down to my computer. The two girls were just stepping into the shower when the camera program came up.

Amy began by using a soapy wash cloth to bath Jenny's chest. She paid attention to her breasts, causing Jenny to moan slightly. They shared a kiss as Amy ran the soapy cloth between Jenny's legs. She spread them apart, giving Amy as much access as she needed. Jenny put both of her hands on Amy's breasts and began fondling them, pinching her fat nipples. Amy pulled Jenny to her, again kissing her as she ran the cloth down her back and down her ass crack. She then got on her knees to clean Jenny's legs, bringing her eye level with Jenny's slit. For just a moment, nothing happened, as Amy continued washing. But all of a sudden, Jenny grabbed the back of her head and pushed her head between her legs, holding her there.

"Clean it good baby," Jenny moaned.

Instead of cleaning it, Amy brought her hand up and inserted a finger into Jenny's ass.

"If I didn't know any better, I'd say my finger was in your pussy right now!" Amy said seeming a little upset that Jenny would do that.

"Ouch!" Jenny protested, "Pull it out!"

Amy pulled her finger out and stood back up washing her hand off. Jenny grabbed another wash cloth and soaped it up. Soon she was washing Amy. She lifted one of her breasts with one hand and washed under it with the other, doing the same thing to the other breast.

"Your breasts are huge," Jenny commented.

"Yeah, I know. Joe liked them though," she replied. Jenny kissed Amy on the lips and said nothing as she washed down between her friend's legs and into her slit. She washed around to her asshole and was soon on her knees washing her legs and feet.

They washed each other's hair and while they were rinsing off, I made my entrance.

I pulled back the curtain. Amy had her back to Jenny with her head turned to the side. They were kissing while Amy used Jenny's right hand to massage her big tits and her left hand to play with her pussy.

"Ladies," I said getting in, "I think you two have played enough for one night. They both giggled giving me a kiss on each cheek. They both bathed me as I had instructed.

We got out and dried each other off and got dressed. Jenny and I stripped the sheets from Amy's bed and put new ones on. Then we all called it a night.

I hid my cuffs, shackles, and strap-on back in their usual place—my locked desk drawer, under a shit ton of old folders and other papers (it was a deep drawer). I made sure to put the movie Jenny had rented in the DVD player. Then I went in the kitchen and made a daiquiri in the blender. I added a shit load of vodka, poured half a glass of it in one of the glasses Jenny usually drinks out of, and put it on the lamptable. I dumped all but a little of what was left in the blender down the sink.

The next morning arrived all too soon. I was worn out and felt like shit. Jenny walked around bowlegged, wincing with each step.

"Joe," she asked groggily, "What did we do last night? I don't have any underwear on!"

"Well," I yawned, still lying in the bed trying to see through the white t-shirt I gave her to dress in the night before, "We watched that movie. You had a few drinks after Amy went to bed early. Then you and I had sex after the movie and then we went to bed."

"I remember Amy going to bed and I remember going to get the movie. The sex explains why I have no bra or panties on," she replied heading for the bathroom.

"All of that was before you made the daiquiris. I told you were making them too strong, but you told me to shut the hell up. So I did," I replied.

"Oh," she said stopping in the doorway seeming to try to remember, "Sorry about that."

She closed the bathroom door to use the bathroom.

"Did you fuck my ass?" she asked, coming out of the bathroom a minute or so later.

"Yeah. You asked me to so I did," I replied.

"I must have been fucked up," she replied.

Still dressed only in the white t-shirt, she walked out of the room in the direction of the living room.

"Damn," I heard her say a few moments later. There was a pause before she walked back into the bedroom, "I made it way too strong! This stuff is wicked! I must have been just totally fucked up."

If she only knew, I thought to myself heading for the bathroom to take a piss. I left the bathroom and put a shirt and some shorts on and headed to the kitchen. There I found Amy and Jenny talking.

"Morning Amy," I greeted her.

"Morning," she replied drinking a cup of coffee. I could tell something was bothering her, "Did you have a good night?"

"I am exhausted. I guess I didn't sleep well," she replied.

"Well, you went to bed early because you didn't feel well," Jenny added.

"I feel okay, I guess," she acted like she was going to say something else but stopped, "But I'm just tired."

And sore, I wanted to add. But there was no way someone that was a virgin was going to know what 'those' sore feelings indicated. To her she was just sore.

"I've got to be going or I'm going to be late," she said a moment later, "Thank you so much for letting me stay here. It was good to see you again."

I helped get her bags back to the car. I wanted to just throw the damn things off the balcony and then pick them up when I got down. But I, again, hauled the fuckers down the stairs and across the parking lot. Jenny decided to call in sick and I was on a mandatory vacation day—I would have lost it if I wouldn't have taken it.

I was sitting in my recliner when she came walking through. I was watching ESPN and drinking what was left of the tea. She was heading into the kitchen but stopped.

"Joe," she began.

"Yeah," I replied thinking 'oh shit' but continued to look at the tv.

"Are we ever going to get married?" she asked.

"I hope we are," I replied muting the sound while turning to look at her. It was one helluva time to be talking about marriage. Here she was home from work because her pussy was gaping open and her asshole was as sore as it had ever been!

"When?" she asked.

"Damn baby, I'm don't have a date," I replied.

She moved around and sat down on the couch, "Can we plan it even though there's no date?"

"Okay," I said after a second of pondering.

"Who are you going to have for groomsmen?" she asked.

"That depends on how many bridesmaids you are going to have," I replied.

"Well, I have thought about that. I don't have a whole lot of good friends. I've decided to ask Amber, Amy, and Cassie to be bridesmaids and I know it's a little uncommon, but I'm going to ask my mom to be my matron of honor."

"I've never heard of the mother doing that," I replied,

Jenny's mom, Maggie, was 45 years old. She stood at 5'7, 155 pounds, and wavy, shoulder-length, light brown hair. Like Jenny she needed to loose a few pounds here and there, but for the most part, she was just and older version of Jenny. Her breasts were definitely bigger than Jenny's, definitely in the mid-to-upper C range. Her ass was rather large and her stomach was a little larger than she would have liked. It didn't matter what she wore (jeans, pants, scrubs—she worked at a doctor's office), they were always tight across her ass and stomach.

"You're only going to have four bridesmaids?"

"What's wrong with that?" she asked.

"Nothing's wrong with it. I just assumed you would have more," I replied, "What about Jill?"

She grew up with Jill but had lost touch over the past few years. Jill was 24 years old and much taller than Jenny at 5'9. She was skinny at probably 105 pounds. Her tits look to be A's, with shoulder-length, blonde curly hair.

"I thought about her, but it's been so long since I've talked to her, I decided maybe I wouldn't ask her," she replied. "Hell, Jenny, you two grew up together," I responded, "Besides, I had five guys in mind for groomsmen. If you only have four bridesmaids, how am I going to have five?"

"So do you want me to ask her?" she asked.

"I don't really care," I quickly responded.

"Fine, I'll ask her. I still have her number in my phone. So it won't be a problem," she replied. At almost the same moment, her cell phone rang. It was in the bedroom. She left to answer it and I turned the television back up. After a few minutes I could hear Jenny on the phone speaking loudly telling someone to go 'fuck themselves.'

She stormed back into the room still pissed, "That bitch!"

"What?!?" I asked half interested.

"My sister is being a bitch like usual," she replied not going any further. A moment later, her phone rang again, "Surprise! It's Becky."

She had always clashed with her step-sister Debbie and her step-mother Becky. Jenny and Debbie were three years apart in age and while growing up they argued like a lot of sisters who are close in age. Instead of taking a more neutral role, more times than not Becky was siding with Debbie. So when they were little girls, Becky punished Jenny constantly. This trend continued through high school and apparently the arguing was never going to stop.

She slammed the phone down after a minute, "Fuck her. I don't care if I never see either one of them again."

Debbie is 22 standing 5'8 or 9, weighs 160 pounds, with straight, black, and shoulder-length hair. She wasn't muscular by any means, but if she and Jenny were ever to tie up in a catfight, my money was definitely on Debbie. She was a little bit chunkier than Jenny, her hips flared more and her breasts were easily D cups. She always dresses down, as if she doesn't know how to dress up. She's most definitely "do-able" but nothing to write home about.

Becky, on the other hand, was in her mid-forties. She was 5'7, 150 pounds, curly, with shoulder-length hair. Her breasts look to be large C's. She, like Maggie, has a really large ass and likes to pull her jeans or pants up seemingly to her bellybutton. She also has a few extra pounds around her stomach too. Though she isn't as pretty as Maggie, she's definitely not a bad looking woman, who needs to get rid of a pound or two. I would fuck her brains out. But I definitely wouldn't tell Jenny.

Several days passed without any new events happening. I spent much of my downtime editing and re-editing the video that I had gotten. Another great feature about the camera system I have is all I have to do is freeze the frame and push 'print' and I have myself a regular still-shot photo. I had to go to Office Depot three times for printer ink and photo paper. I also purchased a 500 re-writeable DVD's to have if I needed. I went ahead and made ten copies of what I had already—and I had a lot.

I called Nick Stevens up to see if he knew anyone who could get me a deal on some jewelry. He did, so I got a princess cut, white gold, 2-carat diamond engagement ring for $900. Even I knew that sounded too fucking good to be true. But Nick swore on a stack of bibles that the diamond was authentic. It really didn't make a fuck to me. I didn't care about marrying her. I just needed her to think I did.

The next day, I got home from work after Jenny. She was in the kitchen reading a magazine and drinking a coke.

"Get dressed. Let's go out to eat," I said walking into the kitchen.

"Okay," she said surprised.

There was only one place in our town that you would consider calling 'nice.' It was, actually, a really good place to eat and the atmosphere was really relaxed. Their specialties were steaks and seafood, though I believe they are much better at the former.

"Joe," she said again surprised as we pulled into other restaurant parking lot, "this is a really nice place. I can't believe you thought of this."

"Aw hell, baby, we hardly ever go out," I replied, "There's nothing wrong with going somewhere nice on occasion."

I parked the car and walked around to open the door for her, again surprising her. We walked to the entrance and five minutes later we were seated. It was the middle of the week, so they were slow.

She ordered bourbon and I decided on a Budweiser. Jazz was playing softly over the sound system helping to drown out what noise was created by the small number of clientele.

"This is so lovely," she said quietly.

I took a sip of beer and nodded my agreement. The waitress took our orders and twenty minutes later, I was working on a Ribeye. She had chosen the fried shrimp. We ate in silence for fifteen minutes before finishing our meals.

I wrote a note on a napkin and handed it to the waitress when she came to clear our dishes.

"What was that all about?" she asked smiling.

"I told her I wanted to speak with the manager," I lied, "My steak wasn't cooked correctly."

"You sure ate it like it was," she said getting a little angry that I would do something like that.

A few minutes later, the waitress brought two champagne glasses and a bottle of their finest champagne.

"Oh my," Jenny squealed delightfully, "This is so nice."

The waitress poured our glasses, leaving the bottle on the table. I fished the ring box out of my pocket, but held it below the table so she couldn't yet see it.

"Jenny," I began my little speech, "We have been together for so long. I should have done this a long time ago."

I then got on a knee, opened the ring box, and asked, "Jenny, will you marry me."

Though I wasn't at the time aware of it, everyone in the restaurant was watching.

With tears in her eyes, the bitch replied, "Yes."

I put the ring on her finger, stood up, wrapped her in my arms, and gave all the appearances of two people happily getting engaged. The entire fucking restaurant clapped. Hell, some of the fuckers even cheered, like it was a ballgame or something. Hell, if you can 'score' on a girl for seven years, getting engaged is like a career ending injury, and marriage is having to fucking retire—the fun and games are all over with!

We left the restaurant and headed back to the apartment. As soon as we walked in the front door, she was on me like white on rice. She slammed me against the door as soon as I closed it, working on the buttons of my shirt, while kissing me as passionately as she knew how. If I didn't know any better, I would have thought someone slipped some of that drug in her champagne.

She had chosen to wear a one piece, black cocktail dress. It zipped in the back. It took her all of three seconds to strip out of that, letting it fall in a heap at her feet. She stepped out of it, leaving her in black panties. She pulled me towards the bedroom where she again began kissing me while peeling my pants down my legs, pulling them down all the way to my feet, which put her on her knees, eye level with my stiffening cock, which was making one helluva tent out of my boxer-briefs. She yanked my underwear down and did her best to take my entire cock into her mouth. Normally, she uses her hand to jack me as she sucked. Tonight, however, she held my hips with both hands and began pulling herself onto my cock as quickly and as deeply as she could without gagging. It felt great.

She did this for a few minutes, before jumping up. She stepped out of her panties, sat on the edge of the bed before lying straight back. Because our bed's height, this position put her pussy in direct line with my cock. I picked her legs up and put them over my shoulders.