Rags to Riches

At nineteen, she had led a hard, difficult life and then she met someone who changed everything.

He's tall, ruggedly attractive, well off and wants to have sex with her.

The only problem? He's sixty years old and as horny as Hell!

********

My name is Bobbie Jean Wilkerson. I'm your typical southern girl, not the southern belle version, but the slightly tomboyish, horseback riding, BBQ eating, cowboy loving type. 5' 5" tall about 120 lbs., ample tits, slim waist and a high, firm behind. Folks who knew my Momma when she was my age say I'm a spitting image of her; a headful of thick blond wavy hair, large wide-set blue eyes, long dark lashes and full red lips.

I grew up in a small dirt poor little town in East Texas in a trailer on the proverbial wrong side of the tracks. I was the second daughter and youngest of seven always hungry, often neglected children. My Momma after years of being psychologically and emotionally beat down had turned into a pathetic shell of the fun-loving, high school cheerleader and debate team captain she had once been. My Daddy was a sorry, drunk, son of a bitch, who when he did manage to get a job could never hold it for more that week. His one claim to fame (if you asked him) was "breeding" my Momma. She was knocked up right out of high school when they got married and he had the poor woman constantly pregnant the early years of their marriage until I came along.

It's crazy, but despite the drinking and tumultuous marriage, they were both somewhat religious in other aspects of their lives and raised us, the daughters to be chaste Christian girls. I guess their heavy handed attempts at parenting must have worked for me, but my older sister Rachael Marie rebelled early on, by the time she managed to complete high school, rumors, and gossip about her being the town slut was already at a fever pitch.

I wanted more out of life than a double-wide trailer, a bunch of kids and a sorry excuse for a man who would beat me out of his frustration. I was determined to have that better life. After I had graduated high school, I worked for a year as a waitress at the Lunch Bucket Café over on Lincoln Road. I've always been a friendly, open type of person, and the customers liked me and always left me good tips. Because I was still staying at home, I quietly gave Momma a little rent money each month and after a year, I had saved enough to pay my first year's tuition at the Josephine Rochester School of Beauty and Cosmetology.

Everything was going just as I had planned and I was enjoying my independence. I did well in my studies at beauty school, and though it was tough, I started putting in more hours at the Café and eventually found a roommate and moved out of the trailer.

On my nineteenth birthday, a couple of my friends took me out for dinner and a few drinks to celebrate. Right before dessert my phone began to ring, and the caller id showed it was my brother Jimmy.

"Bobbie Jean?"

"Hey, Jimmy how's it going?" I asked innocently.

"Bobbie, I've got some bad news," he said haltingly. Then taking a deep breath he blurted out, "Daddy got into a fight over at Magnus' Bar, and he got stabbed pretty bad."

"What hospital is he? I'll meet you there," I said as panic rose in my chest.

"No, no Bobbie Jean, listen . . . listen," he said sounding as if he were about to cry. "Bobbie, Daddy's dead. Momma's in the hospital; she had a nervous breakdown or something."

With those words, my head began to spin and feel as though wrapped in cotton. The sound and voices in the room became muffled and far away and then the blackness.

*****

My life changed that night, more than I could ever have imagined.

Because there was no insurance, the little money I had saved for school was added to what my brothers' could contribute toward paying for a modest funeral. I eventually had to drop out of school because I couldn't afford the tuition any longer, and started job hunting, hoping to find something that paid better than my waitressing job.

Discharged from the hospital after a two week stay, Momma returned home. It was a slow process, but Momma started getting better. I know it's not nice to say, but as much as I loved him, now that Daddy was dead she had her whole life ahead of her, a life she could shape into what she wanted it to be. Though she was getting better, she was still in no condition to be on her own, and I decided to stay with her for as long as she needed me to be there.

A friend told me about the opening for Nurse Assistant at Geneva Nursing and Rehabilitation Center. Although I had no real experience, I figured I had nothing to lose in going to the interview. To my surprise, with my friend's recommendation, I got the job.

My responsibilities were non-medical, mainly assisting the resident when needed, keeping their bed and rooms clean, helping them dress, shower, eat, etc. and if they seemed open to it, just reading and talking with them, sometimes watching television most of all providing a little person to person companionship. Surprisingly I discovered I enjoyed working at the nursing home and found myself looking forward to seeing some of the residents each day.

One resident that I particularly enjoyed seeing and talking to was Michael Sullivan. Mr. Sullivan was probably in his late sixties and had been widowed about six years. From what I heard from the staff, Mr. Sullivan even in his sixties was still a strong, virile man who loved the ladies, and was known to dog around occasionally.

*****

Our relationship started slowly. Each day I would go into his room, sit by his bedside and read to him. After a while, I noticed his expression started to change and soften when I came into the room. Sometimes when I helped him dress, or wheeled him outside for a little fresh air in the courtyard, his hands would wander, and he would playfully reach for and caress my breast and even once or twice "accidentally" slipped his hand between my legs and squeezed my thigh. At the time, I did not take him seriously and would laugh at his boldness and brush his hands away. After all, this was an old man.

Mr. Sullivan was at Geneva Rehabilitation recovering from a skiing accident, though fit and healthy otherwise, he needed quite a bit of physical therapy. He was still not able to get around on his own and so each day I would help him to the shower, or if he did not feel up to it, I would pull the privacy curtains around his bed and give him a sponge bath. I had been doing this for several weeks with no problems, aside from him describing in great detail what he wanted to do to me and stealing an occasional feel. He would lie there on his stomach while I washed his back with the warm, soapy cloth sometimes emitting a soft snore as my ministrations lulled him into a short catnap.

"Ok, Mr. Sullivan, I need you to roll over onto your back now."

He'd turn over and position himself comfortably on his back, his arms at his side, his muscular legs relaxed, his penis, long, thick and uncut lying flaccid on his upper thigh. With me blushing at the sight of his impressive male equipment, a barely concealed smile would play across Mr. Sullivan's face. In the beginning, I tried covering his privates, but he would remove the towel and toss it on the floor, silently daring me to do anything about it. After a while, I didn't bother anymore with the towel.

With the warm cloth, I would wash his broad, muscled chest, and arms then move downward to his legs and thighs before attending to his more intimate areas. One day during his bath, I spread his legs open wider and felt his cock twitch against my hand. Startled, I stood there stupidly staring at it. To my embarrassment, I watched as it slowly jerked becoming firm and full. I looked at Mr. Sullivan and saw him smiling at me with a lustful look in his eyes.

"Take it in your hand Bobbie Jean and hold it," he said. "Don't be afraid, hold it and pull back the foreskin." My heart was beating so fast and hard my chest hurt.

"Go ahead little girl . . . do it."

Timidly, I reached out and took his cock in my hand and immediately felt it begin to harden and grow even bigger.

"That's a good girl," he said. "I've liked you from the time you first started visiting me, Bobbie. I could tell you wanted to take care of me, he said in a raspy voice. A young, pretty girl like you knows what an old man needs, don't you?"

Unsure what he was talking about, I looked at him with a puzzled expression on my face.

"Taste it baby girl, just lick it a little, better yet, put it in your mouth."

Don't ask me why, because I don't know why. I hadn't had that much experience other than sucking my boyfriend off now and then, but I bent over him and did what Mr. Sullivan asked. Stroking and licking him until he became rigid and hot I could hear him groan under his breath when I slipped his purple cockhead through my parted lips into my warm moist mouth.

"Oh my God, Bobbie, that's it, baby girl, you're getting this old man so fucking hard," he said breathlessly. I don't know why I did it, but I began to suck his cock. He ran his fingers through my hair and held my head in place as he immediately began stroking into my mouth trying to make me deep throat him. I couldn't breathe and began to struggle to break free; he finally loosened his hold, and I pulled my mouth off his swollen cock and stumbled back away from him, my eyes practically bulging out of my head.

"I'm sorry Bobbie Jean, I didn't mean to frighten you; it's just that it's been a long time, and when I felt your beautiful mouth on my cock, all I could think about was how good it felt."

I looked at him in disbelief, and in utter mortification ran out of the room. As I hurried toward the door, I saw Jack, the man who shared the room with him sitting up on the side of his bed watching me, his old wizen cock tenting in his pajamas. He had heard everything that had happened on the other side of the curtain.

I never had any trouble with Jack until after that incident. Jack had threatened to go to the administration and tell them what had happened between Michael and me, which would have meant me losing my job. He promised not to say anything if I would occasionally jerk him off during his bath time. Disgusted by his proposal, I agreed, not knowing what else I could do . . . I needed my job.

From then on, every week or two I would jerk the old bastard until he came. He liked it best during his bath. He'd recline in the warm bath water, and I would sit at the side of the tub with my breast exposed and nipples hard and erect from him fondling them. Slipping my hand into the water, I'd take hold of his limp dick, massaging and stroking him until it began to swell. It never ceased to amaze me how big he became when he was fully erect and how much cum would shoot out of his ancient cock and into the warm water when he ejaculated.

Age aside, Jack was still a man and sometimes tried to get me to let him put it in my mouth, but I made it clear to him that that was not going to happen, and he reconciled himself to my jerking him off and fondling his balls.

*****

I didn't see Mr. Sullivan the following week, and I didn't tell anyone what I had done. Whenever scheduled to attend him for his bath, exercise, reading, etc., I managed to find someone to cover for me; but I couldn't keep doing this without drawing attention and questions from other staffers and my Supervisor.

I had seriously started thinking about finding another job when I received a letter from the beauty school's admissions office. The letter stated that a Mr. Michael Sullivan had paid my tuition for the upcoming school year in advance. I thought some mistake had been made and wasted no time calling the school. The Registrar said there was no mistake; Mr. Michael Sullivan had paid the full tuition. I was dumbfounded and suspicious, wondering what his motives were.

Gathering what self-composure I could muster, I opened the door and walked into Mr. Sullivan's room.

"Bobbie Jean, I'm so happy to see you. Please come on in and sit down," he said jovially pointing to the side of the bed.

"I haven't seen you in a while. When you didn't come back, I hoped you weren't angry with me or worst yet afraid of me." He said watching me closely, trying to gauge my response.

"No, everything is fine Mr. Sullivan," I said. "I just wanted to say 'Thank You'."

"No thank yous are needed, little girl," He said. "I wanted to do something that would show you how sorry I am. I didn't mean to frighten you before. It was my fault; I assumed too much. I know things have been hard for you Bobbie Jean, your Momma's bad health, your Daddy passing away and you having to drop out of school."

"How did you know all of that?" I asked tears beginning to well in my eyes.

He got up out of his chair and walked over to me. Sitting down next to me on the bed, he took my hand in his.

"It doesn't matter, baby girl, you don't need to worry, everything will be ok from now on," Mr. Sullivan said as he lowered my hand so that it cupped his covered genitals.

When I tried to pull my hand away, he held it tighter. "I'd like to help you and your Momma, Bobbie Jean. Would you like me to do that for you baby girl?"

After a long pause, I looked up at him and in a barely audible voice answered, "Yes."

"Yes, what Bobbie?"

"Yes, I would like you to help me."

"Good, good girl," he said as he slipped my hand into the band of his pajama pants, where I could feel his semi-hard cock starting to grow rigid. With his hand on top of mine, he placed my fingers around his engorged cock, and I reluctantly began stroking it. His erection was strong and hard, belying his age. As I stroked him, he relaxed back onto the bed and opened his legs wider. His breathing became fast and shallow until he exploded, his warm white cum filling the crotch of his pajamas. I untied the top of his pajamas and helped him out of them, before taking his cum covered cock into my mouth and cleaning him as he instructed.

While I licked his shaft and sucked cum from his balls and I could hear him softly moaning, and ever so slightly sway his hips in a humping motion into my mouth.

"Fuck, Bobbie Jean, that feels good," he said holding my hair back from my face as his body prepared to cum again.

Our unspoken liaison was struck.

*****

For a while, I felt Michael was holding his payment of my tuition over my head to persuade me to be sexually cooperative and accommodating to him. As time went on, however, I found myself eagerly looking forward to our time together.

One day Michael mentioned that there were fewer people during the evening and early morning hours, and at his urging, I made a few changes to my schedule. Twice a week I would work the day shift, and the balance of the week, the evening.

Michael looked forward to my visits on the day shift. There were people constantly in the halls and in and out of the rooms, which meant there was always the possibility that we could be caught pleasuring each other in one way or another. The thought of this excited him, and it sometimes seemed as if Michael was in a constant state of arousal.

His cock was at attention under the sheets when I walked into his room one morning.

"Have you been playing with yourself, Michael?" I asked upon seeing him.

"Of course, baby girl, I was thinking about you."

Seeing the lust in his eyes and the way he slowly fondled his dick, I pulled the privacy curtain closed and unbutton the top of my uniform letting the bodice fall about my waist as I moved to his bed. He had instructed me early on not to wear a bra or panties when I came to work, and so I was never encumbered by underwear when visiting Michael. As I stretched out next to him, he claimed the closest tit and began licking and sucking as I stroked his dick. The fear of being discovered intensified what we were doing and on more than one occasion, one or both of us would orgasm there on his bed.

During the night, if things were slow, I would sometimes go into his room pull back the covers and orally satisfy him as he slept (or pretended to sleep), all the while aware that his roommate Jack was probably listening and jerking off in the next bed.

"Sit on my face," Michael said one night when I bent over him blowing his joint.

I hesitated, not sure what he wanted me to do. "Ride my face," he said again, but more insistently. Finally understanding what he meant, I stood and hiked my uniform skirt up over my hips. With him on his back, I climbed onto the bed, straddled his face and lowered my pussy to his mouth. I don't think I had ever felt anything like what he did to me that night with his mouth and tongue. All I remember is lifting my arms and holding on to the overhead transom as I rode his mouth until I came hard and wet filling the small room with barely muffled cries of satisfaction.

I collapsed over him in a hazy sexual exhaustion, and this old codger whom I had, in the beginning, thought frail and weak turned me onto my back and began to finger fuck me to another orgasm. When my second orgasm began to calm, I changed position and sucked him hard and fast until he spewed his surprisingly copious load deep into my throat.

*****

I remember the first time Michael and I had sex. It was late one quite evening, and I was supposed to be in the supply room taking inventory. Instead, I had crept into Michael's room, locked the door and after slipping out of my uniform, gotten into bed with him. I had intended just giving him oral sex, but one thing led to another and before I realized what was happening, his large hands were caressing my young, eager body, making me quiver with desire. Michael pulled me closer to him as his hands explored my body, his fingers inevitably finding their way to my wet pussy. I felt him insert several fingers inside me, fingering me as he whispered words of reassurance into my ear.

"Everything will be fine baby girl; your old, sweet daddy is right here, and I plan on taking good care of you."

Curled up next to him, I relaxed and allowed him to caress and fondle every part of me. Michael parted my thighs and mounted me. There was a distinct sensation of pain and pleasure as his monstrous cock coaxed my pussy opening wider. I lay there under him, and could feel myself stretching for him. It hurt. Michael began a slow, shallow stroking motion, going deeper with each push, and then he stopped. He thrust his hips again but met the same resistance. He looked down at me and said in a questioning voice, "Bobbie, Bobbie Jean. You haven't been with a man before, have you?"

"No," I replied after a long, drawn out pause.

"Why didn't you tell me?"

"I don't know. I was afraid at first because you were so big, I thought if I did it real good, sucking your dick I mean, it would be enough."

"I can't do this baby, it's not right," he protested halfheartedly. "You sucking my dick and me eating your delicious, sweet pussy are one thing, but for this sixty-year-old cock to be the first to possess your young, new pussy, just seems wrong."

"I want you to, Michael," I said.

He looked at me, torn between what his mind screamed was the right thing to do, and his dick which only wanted to feel the warmth and tightness of my young, innocence pussy. I could see in his eyes that his resolve was quickly fading.

"Please, Michael. Please, don't make me beg."

Michael slowly resumed his shallow stroking and watched my face soften and relax. Suddenly with a hard thrust, he tore into me taking my virginity in spite of his expressed concern and reservations. He covered my mouth with his hand and silenced my scream as I began to struggle, trying to get him off me. Michael put his full weight on me and continued thrusting until the pain ebbed and I calmed.