Play It Again, Sam - Cover

Play It Again, Sam

Copyright© 2008 by POL

Chapter 2: Jennifer

Time Travel Sex Story: Chapter 2: Jennifer - A few readers requested that I upload all five books of the "Play it again, Sam" story in one piece. So, for those readers - Here it is, with a number of spelling and other such errors corrected. Sam Eldon finds himself transported back in time twenty some years and into a much younger body. This is the story of how he affects the lives of many others and discovers what destiny's true purpose has in mind.

Caution: This Time Travel Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Consensual   Romantic   Science Fiction   Time Travel   DoOver   Group Sex   Harem   Oral Sex   Anal Sex  

I quickly rushed out to the living room trying to catch Jimmy's mom before she got away believing she had somehow entered the wrong apartment. Being sober I prayed this reunion with his mom wouldn't turn out to be like a free visit to Belleview or perhaps a monkeys' tea party at the zoo where a disgruntled worker has filled the teapots with whisky. And also the monkeys have been lobotomized and injected with a drug that makes them extremely stupid, aggressive and nasty. I still couldn't fix it in my head that Jimmy might be pimping his own mother and to say I felt a little tenuous was at best an understatement.

Vicky didn't follow me.

"Mom! Wait!" I called out, "You're in the right apartment."

"Jimmy?" she questioned turning toward me.

She was probably thirty five but she looked older. I could see that at one time she had been much more than just a very good looking woman, but now she looked used up. Her black hair was pulled back and messy and her freshly plucked eyebrows looked like little rolled cigarettes. Her red skirt and white blouse had seen better days. The top three buttons of her blouse were open showing a good amount of cleavage. She just stood there, looking disassembled and I wasn't sure if she was embarrassed or afraid. Possibly she was embarrassed at being caught thinking she had entered the wrong apartment because it was clean for a change.

The guy she was with had the air of a professional drinker about him, both from the puffiness of his face to the fresh and almost severe wound on the bridge of his nose. He stood about five foot eight inches tall and carried a fair sized pot belly. He looked soft and out of shape.

"Hi mom." I said, "Sorry about the confusion. Vicky and I cleaned the place up a little."

You might be wondering why I would even bother to placate this woman that was not only a drunk, certainly a part time whore that perhaps allowed her son to pimp for her, beside the fact that she wasn't even my real mother. Well the reality of the situation was, for the time being anyway, she was my (and Vicky's) only bread and butter. Without her we would both be out on the streets. So for now I needed to keep her happy, at least until I figured out exactly what kind of a relationship we had together.

"Who the fuck are you?!" the drunk guy with the nose problem snapped.

"Hi. I'm Jimmy. I'm her son." I told him while nodding toward Jennifer and extending my hand toward him.

He just looked at my extended hand as if it were some kind of foreign object he couldn't understand. I pulled my hand back and smiled. Then turning to Jennifer I said, "Have a seat mom. Can I get you anything?" I really hoped she didn't want anything. After having disposed with all the biological experiments in the frig there was precious little left inside that dark and damp box, other than a couple of beers and a carton of questionable orange juice.

At that point Jennifer not only looked drunk but very confused as well. I took the bull by the horns and after successfully dislodging her from the nose guy's arm, I guided her toward the couch and then helped her to sit down.

"Have a seat?" I asked the guy.

I could only surmise that the nose guy was starting to consider the possibility that he wasn't going to get lucky that night because he drunkenly growled, "This is bullshit!" Then looking over at Jennifer he said, "What the hell's going on here anyway? You fucking invited me up here. Do you have any idea how much fucking money I wasted on you tonight?"

"Wasted?" I questioned while looking at him very sternly, "I can only assume you spent a very pleasant evening in delightful and entertaining conversation with my amazingly lovely mother here, and I take offence at you calling it wasted money."

"This is total bullshit!" The guy repeated turning his gaze toward me. Fortunately I was at least three inches taller than he was and I was a lot younger and in better shape. I didn't think he would try to take me on.

"Jimmy..." Jennifer said softly. Then just as softly she said, "Glen ... I don't know ... I..."

"Fuck you!" he yelled turning toward Jennifer once again. Then spinning around and almost falling in the process he headed toward the door.

"Was it something I said?" I called after him.

His hand was on the door knob but he paused, turned around and then barked, "Fuck you too!" Then as if remembering something he reached into his jacket pocket and withdrew a pair of panties which he angrily threw toward Jennifer while yelling, "You can keep these fucking things too!" The panties landed several feet short of their mark and fluttered silently onto the freshly vacuumed carpet. Then bad nose was gone.

I picked up the panties and then went over and sat down next to Jennifer. I draped my arm around her shoulders and said, "I'm sorry mom. I just don't like anyone talking to you that way."

She turned her head so she could look at me, "You haven't called me mom in years. What's going on Jimmy? Why are you acting so strange? Did I do something wrong?"

I didn't answer her question. Instead I asked something that hopefully would shed some light on the big question concerning Jimmy's and his mother's relationship. "Mom, why did you bring that guy home?"

She looked puzzled when she answered, "Because we made our deal. You better not be planning on taking any more of the money. We talked about that. Besides, he was no different from any of the others. What? You didn't like him or something? Do you know him from somewhere?"

"No I don't know him mom. But I guess you could say I didn't like him." I didn't know how she would react to my next question but I felt it needed asking. "Mom do I ask you to bring guy's like that home?"

She shook her head as if trying to clear it. Then looking perplexed she responded, "Turning a new leaf Jimmy? As if you really cared. Christ, I'm use to it by now and I realize I need the money to keep you happy. But don't try and change the deal. You said you'd always leave enough to pay the rent and utilities."

Her last few comments had more than confirmed my suspicions that Jimmy was indeed pimping out his own mother. I started hating the guy whose body I was occupying more and more as time went on.

"Mom," I said holding up her panties, "did you have to take these off and let that slime ball feel between your legs?"

"It was the only way I could keep him interested. You know I've done it before. You never said anything then."

"Well, things are going to change around here mom. Things are going to get better, you'll see. I'm really sorry about the past. Okay? I love you mom."

She leaned way back so she could look at me. Her expression was one of total confusion, "Jimmy what's happened to you? Who the hell are you anyway? Are you all right?"

"I'm fine mom. Hey listen I didn't want to intrude on your privacy so we didn't clean up your room. If it's okay, how about you crash out here tonight and with your permission I'll straighten up your room for you?"

Her face took on a look of even greater confusion, if that were even possible, but instead of questioning me she merely uttered a small, "Fine." And then she drew her legs up and stretched them out behind my back. Steady, arithmetic breathing confirmed that she was sound asleep almost instantly.

I went to my bedroom to ask Vicky if she would come out and undress Jennifer for me only to discover my little redhead was already fast asleep her naked body reclining on the bed in front of me, her outstretched neck, her long red hair draping over the side of the mattress, and her small, hard breasts and her soft flat belly rising and falling with each pleading breath. My pulse quickened just looking at her.

I went back to the living room and removed Jennifer's pumps from her feet and then unbuttoned and, with considerable trouble, slipped off her blouse. Getting Jennifer to turn onto her side was a chore but finally having managed it I pulled down the zipper on her skirt and unfastened her bra. Rolling her over once again I stripped off her skirt and bra. She was completely naked now except for a pair of thigh high nylons and I looked down at her. She actually had a very nice body. No that wasn't right; she had an absolutely great body. Her breasts were large and well formed. They sagged a little bit but not so much as to be unattractive. Her nipples were dark, almost purplish with even darker areoles surrounding them. She had a flat, tight belly and a full dark triangle of pubic hair at the joining of her thighs. I rolled down and then removed her nylons. Then after retrieving one of the extra washed blankets I covered her up and let her rest.

It was nearly five am by the time I finished cleaning and vacuuming Jennifer's room leaving all of her washables bundled up inside a bed sheet atop her bed. During the cleaning process I discovered she really didn't have much in the way of clothing, shoes or anything else for that matter. I started to feel sorry for her. Maybe she was a drunk, maybe she was a loose woman, maybe she was even a bad mother, but what had she done to deserve a worthless piece of shit son like Jimmy? Christ the little bastard actually sent his own mother out to pick up men and let them fuck her just so he could get a few bucks in his pocket. And who the hell was I to judge someone else's lifestyle or morals anyway? Besides heaven only knows what kind of crap had occurred in her life that had brought her to the place she was currently at. I decided then and there if she was at all salvageable I would make the attempt.

I stripped off my clothes then I crawled into bed next to Vicky and snuggled up to her warm body. She smiled and sighed softy in her sleep and pressed her naked bottom against me. Three seconds later I was sound asleep.

When I woke up I saw that Vicky was already awake. I also saw that she wasn't feeling well. "Good morning sweetheart," I told her leaning over and first hugging and then kissing her on the cheek.

"I don't feel so good Jimmy." She told me in a strained voice.

"I know baby," I tried to comfort her. "How bad is it?"

"I've been worse, but that isn't saying much." She answered then she tried to smile.

I kissed her on the mouth. "Can you handle it?"

"For you I'll do my best." She smiled again, this time doing a better job of it.

"I know you will. Hang in there baby it'll get better."

I guess she must have noticed the tent my morning hard-on had made in the sheet because she said, "Do you want to have sex? I will if you want too."

"With you I always want to have sex. But I know you're not feeling up to it and this is just a male morning thing. But thank you for thinking of me."

"I'll always think of you Jimmy ... no, I'll always think of you Sam. I love you."

"The feeling is mutual honey," I told her before kissing her again. "How about you just hang out in bed for a while and I'll go out and get us some coffee and maybe a little something to eat? You'll feel a lot better after getting some caffeine and food in your stomach."

"If you think so, okay."

I got up and dressed and then after using the bathroom I went out to the living room. Jennifer was still fast asleep but during the night the blanket had slipped and both of her magnificent breasts had become uncovered. God they looked good! I covered her up and then noticing Jennifer's handbag lying on the floor next to the couch I looked through it and found what I had hoped would be in there, a set of car keys.

I went back into the bedroom and asked Vicky if she knew what kind of a car Jennifer owned. She told me she thought it was about a fifteen year old light blue ford with ripped upholstery and most of its paint faded off.

Looking down at my dear sweet little redhead suffering so badly I felt so much compassion for her that out of impulse I took the baggy filled with power out of my pocket and placed it on top of the dresser. So much for tough love. "Vicky," I said, "It really hurts me to see you in so much pain. Listen honey if it gets too bad I put the stuff up here on the dresser. Try not to use it if you can, but if you do use it do just a little bit. Okay?"

Vicky looked up at me and I swear for the first time in my life I could actually see love in someone's eyes.

Vicky didn't say a word as she slipped out of bed, walked over to the dresser and picked up the baggy. Then taking me by the hand she led me into the bathroom. Once we were inside the bathroom she opened the baggy, dumped its contents into the toilet bowl and flushed. Having that done she stood up on tip toes, kissed me deeply on the mouth, said, "I love you," and then she returned to the bedroom.

I hauled Jennifer's dirty laundry down the elevator with me, then walking first up and then down the block I finally located Jennifer's car. Actually it wasn't that hard to spot, it was the only car on the block that wouldn't have looked out of place in a demolition derby. I threw the laundry in the back seat then after a quick stop at the Laundromat I drove around until I located a small corner combination liquor-grocery store. Besides coffee I picked up eggs, milk, bread, butter, lunch meat, jam, peanut butter, sugar, bacon, and grapefruit juice.

After another quick stop to the Laundromat to transfer the wash into dryers I drove home and lugged the food up to the apartment. When I came in I saw Jennifer sitting up smoking a cigarette, there was a pack of Sir Walter Raleigh cigarettes and a thin gold lighter sitting on the coffee table. She was holding the blanket I had covered her with tightly around her body. She didn't say a word but she watched me very closely as I set the bags of groceries on the kitchen counter.

"Morning," I said to her nodding my head as I passed heading toward the bedroom in order to check on Vicky. My little redhead was sleeping again so I tip toed out of there and went back to the kitchen and started putting away the groceries.

"What's going on Jimmy?" Jennifer's voice startled me. She had come up behind me still holding the blanket around her.

I turned farther around so I was facing her and smiled, "Nothing mom. I just went out and did a little shopping is all. Your laundry's in the dryer down at the Laundromat, I'll go pick it up later. Oh yeah, I hope you don't mind but I borrowed your car, the keys are over there on the counter."

"Don't give me this shit Jimmy! What the fuck is going on!" She stubbed the cigarette she had been smoking out in the ash tray sitting on the kitchen table then she stood and faced me her eyes glaring.

I raised my hands palms up in a display of showing I didn't know what she was talking about and she flinched.

"Are you going to hit me again Jimmy? Go ahead it isn't like I'm not use to it. You can't hurt me any more than you already have Jimmy. Go ahead hit me!"

"Mom I..." I started, but she interrupted me before I could say anything.

"You know I'm willing to put up with an awful lot Jimmy ... I have put up with an awful lot, but I begged you the last time, I begged you Jimmy. That one little thing was all I ever asked of you and you couldn't even give me that. Just that one little thing." Then she started crying.

"Mom," I said, "I don't know what you're talking about."

"Bullshit Jimmy. Bullshit!" then she dropped the blanket revealing her nude body. "Last night you stripped and raped me again. How can you do that to your own mother? With all the things you make me do to degrade myself why do you have take the one little piece that's mine. That one little thing. You promised me Jimmy. After the last time you promised me."

I reached out and took her by the shoulders. She flinched again but she didn't try to pull away. I looked directly into her eyes and I said with all sincerity, "Mom, I swear to you, last night I did not rape you. When you fell asleep on the couch I went to get Vicky so she could undress you but she was already asleep so admittedly I did undress you but I did not touch you. Honest mom I only covered you up."

"Something's not right here." She said and I could feel her trembling with fear under my hands. "You have never acted like this before. Who the hell are you!?" She sounded scared and I looked at her again. She was absolutely terrified.

"Don't be frightened Mrs. Maxwell. He's a different better Jimmy." Vicky said emerging from the hallway. "It took me a while too, but you'll like this new Jimmy a lot better than the old one. I actually love this one. A lot."

Jennifer was turning her head, looking first to Vicky, then to me, and finally, at Vicky again, "What do you mean he's a different Jimmy?"

Vicky smiled, "I mean he's nice and he cares about people. He doesn't do any drugs and he makes love not just fucking. And he's smart too. You've got a son you can be proud of now Mrs. Maxwell."

Jennifer looked into my eyes with such intensity I was almost unable to hold her gaze. "My God. You are somebody different aren't you?" She said this softly and I could tell she had actually spoken to herself rather than to me. Then reaching down she picked up the blanket and covered herself up.

"Yeah." I said just as softly answering her, even though I knew her question had been rhetorical. Then I continued with putting the groceries away.

Vicky came into the kitchen and after opening the can of coffee and getting the percolator ready she placed the pot on the stove and then used a kitchen match in order to get a gas fire going under it.

I stepped over to Vicky then turning her around I asked, "How are you doing sweetie. Hurt much?"

"Not too bad," she smiled, "I had some shakes last night but seeing you this morning made it all better."

I leaned down and kissed her softly on the lips then I pulled back and said, "You're some kind of fighter kid. I'm proud of you."

"Without you I'm some kind of nothing." She whispered. Then she drew herself up, threw her arms around my neck and kissed me with passion.

Through all of this Jennifer had not moved. She just remained standing where she was with that blanket wrapped around her body watching everything we did. Finally she said, "Jimmy ... or whoever the hell you are, talk to me."

I indicated the table and we both sat down. I sensed the difficulties Jennifer was having and tried to phrase my response as casually as possible. I unhurriedly told her the same story I had describe to Vicky. She didn't react, just sat there expressionless without interrupting me. When I finished talking I looked back at her and attempted a weak smile. I think we might have remained there forever just looking at each other without speaking had not Vicky broken the silence.

"How do you take your coffee?"

"Black." I answered.

Jennifer didn't respond so I asked, "Coffee?"

"Huh?" Jennifer said. She was obviously preoccupied within her own thoughts. Then she turned to Vicky and said, "Oh sorry. A little milk and a little sugar please."

Jennifer stood up then after lighting up another Sir Walter Raleigh she returned to the table. Then turning her attention to me she said, "I suppose I should be in mourning over the loss of my son right now, but strangely I'm not. I'm not certain if it's because I can look at you and still see my son sitting here with me, or if it's because I now recognize that over the past two years I lost all my maternal sentiment for him."

Vicky brought our coffees and we both took a sip, then Jennifer drew in heavily on the tobacco filling her lungs, then exhaled sending a plume of blue-gray smoke into the air and spoke again asking a question that Vicky had failed to ask me, a question I had intentionally avoided, "You're older than Jimmy was aren't you?"

I nodded.

"Much older." She said it as a statement rather than a question.

I nodded again.

Vicky joined us at the table with her own cup of coffee and sat down next to me placing one of her hands on my thigh. I don't know if Vicky's interruption had caused Jennifer not to ask the next obvious question, 'how old are you' or if she just didn't consider it pertinent because she took another sip of coffee, another drag on her cigarette then instead asked, "So if you were killed in a car accident and ended up here do you think Jimmy ended up where you were when he died?"

"I can't even begin to guess," I answered honestly trying to ignore Vicky's hand which had worked its way up my leg and was lightly rubbing along my cock over my pants, "seeing as this is my first after death experience the how, why, and what of it is far beyond my comprehension."

Jennifer nodded, took another sip of coffee, another puff, and then she surprised me by asking a question that would have eluded most other people, "In what year did the car crash you were involved in occur?"

I didn't answer at first and Jennifer just kept staring at me over the rim of her coffee cup which remained stationary near her lips.

"2006." I finally answered.

Jennifer didn't flinch, but Vicky exclaimed, "Holly shit!"

When Jennifer reached over to stub out her cigarette, the blanket covering her unraveled at the top and exposed one of her breasts. Dispassionately she reached down and slowly lifted the offending corner that had fallen and re-covered her tit.

I don't know what it was, after all I had seen Jennifer completely naked last night, but when that blanket slipped exposing her tit and the slow casual way she had covered herself, it just seemed so damned erotic to me that I felt the bulge in my trousers involuntarily growing hard. Vicky felt my cock stiffen and she squeezed it several times getting me even harder.

"I really should go and put some clothes on." Jennifer said coolly.

I felt my face flush and as a means to hide my embarrassment I said, "Ah ... most of your clothes are still down at the Laundromat."

"Hmm ... Bra's, panties, everything?" Jennifer asked

"Ah ... I'm afraid so ... even the things you were wearing last night. I ... I washed them all."

"You know washing a woman's under garments is a very personal thing. Beside the fact that bra's and certain other delicate items really should be hand washed."

I flushed again. "Sorry. Ah ... I only wanted to help."

"I know," Jennifer said smiling, "I was just teasing with you. After all it isn't as if you haven't seen me naked before now is it. And most of my personals are in such bad shape even a washing machine couldn't damage them anymore."

"Look, about last night..." I said attempting once again to explain my actions but Jennifer cut me off with a wave of her hand.

"You know, it's really strange sitting here staring at my son's face, yet already I've come to accept you as a total stranger. So tell me total stranger did you like what you saw last night?"

"Look Damn it!..." I snapped but Jennifer cut my words short once again.

"Oh don't get all pissy. I only asked because I noticed your little playmate over there rubbing her hand all over your cock and when I accidentally flashed my tit I swear I saw it get hard. So, did you get a big old stiff boner when you striped me naked?"

Vicky jumped up from her chair so quickly she almost spilled her coffee, then looking daggers at Jennifer she shouted, "I am not his little playmate! I love him more than you could ever know! He's nothing at all like that cruel sadistic bastard you raised! He doesn't demand anything of me unlike your son who made me suck his cock and let him fuck me just so I'd have a roof over my head. Your son was going to get me hooked on heroin and then force me into prostitution! He tried to make me let him fuck me in my ass! This man I would willingly give my ass too! I even offered it to him and he turned me down! This man hasn't even had sex with me yet! Not because I haven't offered, because I have! He's just too damn caring. But he did do some other things for me that made me feel good about myself, that made me feel wanted, cared for, and even loved. So don't go getting all high and mighty about him getting a hard-on when you flashed your tit at him. That's just a normal male reaction, and I already know him well enough to know that when he undressed you it was just so you could sleep more comfortably and nothing more!"

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