By the time I started my freshman year in college I was nineteen. I had visited the university during my senior year of high school and after being shown the college dorms and the fraternity houses I decided that neither were right for me…too damned much noise and I was going to school to study and learn!

I managed to spend a day in the town, where the university was located, and found a nice two room, upstairs apartment not too far from the campus. It was in a home owned by Mrs. Ruby Mathews, a sixty-something year old widow (later learned the Mr. Mathews had died some eight years earlier). Mrs. Mathews told us, my parents and me, that she had never rented rooms to anyone before, but she could use the extra income and decided to give rental a try.

She had only three rules: No drinking, no loud parties or loud music and no girls in my rooms. That last one was going to be a killer I thought. During my visit to the university I had spotted an army of good looking coeds and thought that, at least, a few of them would be willing to take a roll in the hay with me. I knew that the dorms and the fraternity houses weren’t going to condone bringing a coed to your room and now Mrs. Mathews had spoiled my plans even before I had a chance to find a willing coed!

Mrs. Mathews was about the same age as my grandmother, but the similarity stopped there. Oh they both had huge tits, but my gramma was damned near as wide as she was tall. Mrs. Mathews, on the other hand, was tall and slender with a little round tummy and where gramma’s hair was silvery white Mrs. Mathew’s hair was coal-black. Mrs. Mathews was not what you’d call pretty, but she was a handsome lady and impressed me as being a very nice lady.

When I returned to start my first semester Mrs. Mathews had given me a key to the front door. My room was located on the second floor and when you entered the front door the stairway was on the left side of a long hall. At the far end of that hall was Mrs. Mathews bedroom and master bath. I didn’t know it then, but that layout was to have a definite affect on me for the rest of my life.

When classes started Mrs. Mathews asked for a copy of my class schedule. I didn’t know and didn’t learn until months later why she wanted it. I finally learned that it was because she often did her housework in the nude and wanted to be sure that I wouldn’t be around to catch her at it.

Just three weeks into the first semester my two o’clock freshman English class was canceled because the professor was sick that day. At first I thought I’d go to the student union and check out the coeds, but decided, instead, to go back to my room and organize my chemistry notes, while the lecture was still fresh in my mind.

Mrs. Mathews didn’t hear me come in and when I turned, from closing the front door, Mrs. Mathews came out of her bathroom and stopped in front of the open door of her bedroom. She wasn’t wearing a stitch of clothing! She bent at the waist and began drying her hair. Her big, old saggy tits swayed vigorously as she dried her hair. She was standing so that I had a three quarters view of her body and I could plainly see the dense, black thatch of hair between her legs.

I was afraid that she’d catch me watching her, so I hurried up the stairs being careful to make no noise. I dropped my books on the bed and hurried to the upstairs bathroom. As I jerked off I closed my eyes and in my minds eye I could see her huge tits swaying and the dark bush between her legs.

I went back to my room and thought about what I had just seen. I had never fucked anyone over nineteen and had never imagined screwing anyone over the ripe old age of twenty-five, but all of that had changed now! I knew that I was going to fuck Ruby Mathews or die trying. Getting my cock into her hairy old cunt quickly became an obsession. I knew that this was going to take time and planning, I wasn’t just going to grab her tit, show her my pecker and expect her to jump right into bed with me.

She’d probably slap the shit out of me instead!

I decided to use a variation of the plan I had used to get into the panties of three different girls when I was in high school. I had taken those three to dinner, the movies, but the most important thing was that I never passed up an opportunity to compliment them on their hair, their attire, etc. I sent them cards for Christmas, Easter, Valentines Day, etc. In short I made each of them feel that they were special to me. With some variations I was sure the same thing would work with Ruby Mathews.

I decided to put my plan into action that very evening. When I went down stairs, to go out for my dinner, Mrs. Mathews was in the front hall. After speaking to her I said, “Mrs. Mathews your hair looks very nice this evening.” She smiled and thanked me. As I went out the door I smiled and thought, “I think this is going to work, but it’s going to take some time. She’s probably never even considered taking a guy my age to her bed.”

It’s not necessary that you believe every compliment you pay your intended “victim”. What is important is that you sound sincere! Your “victim” must believe that you mean every word! However, I had told Ruby Mathews the truth, this time, her hair really did look nice, clean, shiny and nicely styled.

I had noticed a box of chocolates in Mrs. Mathew’s living room so the next week I sent her a one-pound box of the very best chocolates I could find. Along with the chocolates I sent a card thanking her for allowing me to live in her home. I had them delivered instead of taking them to her myself! From watching my mother and older sister I had learned that a woman is much more impressed if you have the gift delivered than if you take it to them yourself! Don’t ask me why, they just are! As I learned after I started working for a living, if you had the flowers or the gift delivered to their workplace they were really impressed.

Later that afternoon, when I got home from class, Mrs. Mathews was waiting in the hall. She smiled, put her hands on my shoulders, thanked me for the chocolates and kissed my cheek. As she leaned in to kiss my cheek her massive old tits pressed lightly against my chest. I told her that no thanks were necessary, that it was me that was thanking her.

When I got to my room I whispered, “Yessss, it’s starting to work! Now I just have to keep it going.”

Each time I saw her for the next week I complimented her for something…her dress, her hair, something and Mrs. Mathews was becoming more and more friendly and I’m sure that she didn’t suspect a thing.

Near the end of the month I learned that her birthday was less than a week away so, on her birthday, I sent her a dozen long stemmed, red roses with a birthday card enclosed. They were delivered before I got back from classes that afternoon. Again Mrs. Mathews was waiting in the hall. She wore a broad smile and said, “Paul it was soooo thoughtful of you to send me roses, I don’t know how to thank you, you’ve brightened an old lady’s day.” I knew how she could thank me, but it was still much too early. She put her arms around me and I put mine around her waist, as we hugged she kissed my cheek and, not to be outdone, I kissed her on both cheeks and wished her a happy birthday. Her massive jugs were pressed firmly against my chest and she thanked me again for the roses before we released each other.

After she stepped back she told me that two of her friends were taking her to dinner and that they were coming back for coffee and cake afterward and invited me to join them. As part of my plan, I tried, but not too hard, to decline the invitation, insisting that I didn’t want to spoil her visit with friends. She insisted that I join them. Finally I agreed to have coffee and cake with them.

Oh, I almost forgot to tell you one of the most important parts of my seduction plan. Every time I got the chance, and I confess that I made the opportunities, I touched her. Maybe it was just a pat on the hand, or on the shoulder, sometimes, and it was rare, I brushed against her. Whenever possible I touched her bare skin, that’s important. I managed to get a hand on her, somewhere, every day. None of my contacts were of a sexual or sensual nature. I just touched her. The first few times she tended to pull away, but she soon got used to my touch. I know that she thought it was just my nature, but every touch was planned to get her used to the feel of my hands on her body. This was to pay dividends later on.

I continued using my plan of sending her cards, complimenting her on her looks, touching her and added an occasional trip to the movies or to the university auditorium to hear a concert for nearly another entire month. Things were progressing nicely. At the movies one night, during a particularly emotional love scene, Mrs. Mathews took my hand and didn’t let go until the movie ended. I didn’t make any comment and made no attempt to take things any farther.

One Friday afternoon, at the end of that month, I was in my room working on some chemical reaction problems the professor had given the class. I was studying wearing only a pair of briefs. I heard Mrs. Mathews calling my name. I opened the door and stood behind the door, as if I was modest, but I was careful to expose just enough of my body that she could see what I was wearing. She was at the foot of the stairs and I was a bit surprised at the way she was dressed. She had on a tight white blouse cut low enough to show a healthy amount of cleavage, a black sheath skirt which struck her just above the knee, black high heels and nylons. When she saw how I was dressed, or rather undressed, she smiled and then said, “Paul I just took an apple pie out of the oven. Would you like a piece of pie and a cup of coffee?” When I told her that I would she asked, “Would you like a piece of cheese on it?” When I told her that I would she said, “Well hurry! It’s best when it’s nice and warm.” I thought, to myself, “Yeah and hair pie is best when it’s hot and wet!” I told her that I’d be right down and, pretending to get out of the way so that I could close the door, I made sure that she got an eye full.

As I was dressing I thought, “I’ll be damned! I think the old broad is trying to seduce me. Just look at the way she’s dressed.” It was fine with me if she thought that she had seduced me, instead of the other way around. After all it’s always best if the lady thinks that she’s the one responsible for the seduction. It means that she doesn’t think that you’ve done anything to force her!

I dressed quickly and hurried downstairs. Mrs. Mathews was waiting at the foot of the stairs and when I reached the bottom she took me by the hand and walked with me to the kitchen. I thought, “I’m real, real close to getting into her bed!” She indicated a chair at the kitchen table and asked me to have a seat. When she sat the pie before me she placed her free hand on my shoulder and pressed one of her monstrous melons against my back. “Much, much closer to getting into her bed!” I thought.

As we ate our pie and sipped our coffee we talked about this and that and all the while she looked at me and smiled. After about ten or twelve minutes she sat down her cup and said, “I could use some more coffee, how about you?” I nodded and said, “Keep your seat and let me get it. After all it’s the least I can do for such a great piece of pie and pleasant company.” I brought the coffee pot to the table and as I poured her coffee I put my hand on her back and lightly ran it up and down. I was testing the water to see how she’d respond to a touch that was a bit more than the casual touches I’d used before. Ruby Mathews sighed and said, “Paul would you be a dear and massage my shoulders? They’re kinda tight.” I replied that I wouldn’t mind at all and after returning the coffee pot to the maker I stood behind her and started rubbing her shoulders. I continued my massage for nearly ten minutes and all the time Ruby was sighing and saying how wonderful my massage made her feel. When I finished I kissed the back of her neck and asked, “There, how’s that?” A little shiver ran through her body and she replied, “Ohhh Paul that was just wonderful.”

After a second cup of coffee she said, “I have a roast in the oven that should be done by six. Why don’t you have dinner with me this evening?” I told her that I didn’t want to put her to any trouble and she said that she got tired if eating alone and would appreciate my company.

At six I went back downstairs. We ate in the dining room and shared a great meal. She was still wearing the same white blouse, black skirt, high heels and nylons that she wore earlier and after we finished eating she invited me into the living room to watch TV. She pointed to a chair and asked me to have a seat. She took a seat on the sofa and the skirt rode up a little, revealing four or five inches of her surprisingly firm, smooth, shapely thighs. Fifteen minutes into our TV viewing she coughed and when I looked at her I saw that her thighs were parted just enough to give me a view of the crotch of a pair of shiny, white panties. I pretended not to notice, but from the way she acted for the rest of the evening I think she was either waiting for me to make the first move or else she was trying to get up the courage to make that move herself! Nothing happened that night and as I prepared to return to my upstairs room Ruby asked if I’d help her rearrange some furniture in the morning. Naturally I told her that I would be glad to help. As I was leaving Ruby invited me to have breakfast with her at seven-thirty Saturday morning.

When I sat down for breakfast it was apparent, even though she was wearing a loose fitting shirt, that she wasn’t wearing a bra. After breakfast as we were moving furniture she managed to brush her big saggy tits against me several times and once when she stood behind me to point out the position of a chair her tits were pressed firmly against my back. Each time she had rubbed her tits against me my pecker grew a little harder and now that she had her tits pressing against my back I had a full fledged hard on. “Now’s the time!” I thought. I turned, put my arms around her waist, pulled her close and kissed her. She made no effort to pull away. Instead she pressed her little, round belly against my cock and opened her mouth, inviting my tongue to probe her hot mouth. During our kiss I pulled her shirt out of her pants and slipped my hand under it and onto her bare back. She moaned and leaned back, inviting me to slide my hand to the front and grab onto her big tit. “Ohhh Paul.” She sighed, “Your hand feels sooooo gooooddd!” She took one hand from around my neck and worked it between us and gripped my swollen prick.

After another passionate kiss I said, “I think we’d better go to the bedroom, but first let me see those fabulous titties!” She smiled and started unbuttoning her shirt, with one hand, her other hand still held on to my stiff cock, my hand was still holding her monster jug. When her shirt was unbuttoned I helped her get it off and then, after giving her tits a real good look, I lifted one, leaned down and sucked it into my mouth and started flicking her big nipple with my tongue. Ruby put her free hand on the back of my head and said, “Ohhhh Paul your tongue feels soooo gooooddd! It’s been years since I’ve had my titties sucked.” Her nipple was as big as the tip of my index finger and was so sensitive that in less than a minute the action of my tongue made her cum.

She released her grip on my pecker, put a hand on each side of my face, kissed me and said, “Please baby let’s go to the bedroom.”

After another passionate kiss once we were in her bedroom I started to unbutton the waistband of the jeans she was wearing. Ruby said, “My God I can’t believe I’m doing this with a boy young enough to be my grandson.” That was my cue to get her out of her pants as quickly as possible, before she changed her mind! I might never get another chance at her old cunt. As soon as I slid the zipper down I crouched and, with one quick tug, pulled her jeans and panties down to her ankles. I dropped to my knees, put both hands on her ass and buried my face in her curly haired muff and kissed her belly just above the lips of her pussy. “Ohhh yesss Paul.” She groaned. I stood, sat her on the edge of the bed and finished getting out of her pants and panties.

I stepped back a couple of steps and started getting out of my clothes. Ruby watched intently and when I stood naked before her she smiled and looked at my stiff pecker with eyes as big as saucers. “Ohhh Paul you have such a big, lovely penis why it’s bigger than Harry’s was.” (Harry was the husband that she had lost eight years before). I stepped close to her and she raised a hand and grabbed my prick. I let her hold and stroke it for a few minutes. I didn’t ask her to kiss it. I didn’t know how she felt about oral sex, but I was soon to find out. “Lay down.” I said. She released my cock and scooted into bed and I was right behind her.

I took her in my arms and after a kiss I sucked a tit into my mouth slid two fingers into her wet, slippery cunt and tongued her tit and fingered her old pussy until she had cum two or three times. I released her tit and kissed my way down over her round tummy to the very top of her cleft. After nuzzling her curly bush I got between her legs and kissed her on the pussy lips. I had gone down on every girl I had fucked while I was in high school and now I was curious to learn if there was any difference in the taste of a fully ripe, mature pussy and the teenaged ones I had tasted in high school. For several seconds I was content to look at her old pussy. The hair between her legs was long, black, curly and as fine as silk with a few gray hairs here and there. The cleft between the lips wasn’t as tight as the girls I had screwed in high school, but she still looked good enough to eat and that’s what I intended to do. I parted the lips and ran my tongue over the hot, wet inner pussy flesh and then sucked her clit into my mouth and flicked it with my tongue (her vintage pussy, like fine wine had been aged to perfection and was every bit as tasty as any of the others I had ever eaten). Ruby lifted my head and said, “If you’re going to do that turn around and let me suck your big, beautiful cock.” I had never heard her say anything like that before and it excited me. She was always very prim and proper. I smiled and said, “Okay, but I’ll let you know before I cum.” She smiled and said, “Ohhhh I think I’ll know when you shoot your sweet, hot jizm into my mouth.”

I couldn’t believe my ears! She was telling me that she wanted me to cum in her mouth. Of the three girls I had screwed in high school only one would even let me put my cock in her mouth and she wouldn’t let me cum in her mouth! Now Ruby Mathews, my sixty something landlady, was going to give me my first, honest to God blowjob!

I lowered my head and sucked her swollen clit into my mouth and went to work with my slashing tongue. At the same time I started pumping my pecker into her mouth. I was so damned horny and it had been nearly three months since I’d last fucked Janice Moore that I wasn’t able to last very long. Thankfully Ruby was as horny as I was and my flicking tongue made her cum two or three times before I blasted a big load of thick, hot cum into her sucking mouth. As soon as my dick stopped spewing its heavy load I started to pull my cock out of her mouth, but her hands were on my ass and she held me tight. I could feel her mouth and throat work as she swallowed my heavy load. She finally released me only after I had gone totally limp in her mouth.

When I turned to lie beside her she kissed me and said, “Ohhh Paul that was fantastic. It’s been sooo long since I’ve tasted a man’s cum. Harry used to cum in my mouth all the time and I just loved it. I thought that I’d never get to taste it again. And I have to tell you that your jizz tastes every bit as good as Harry’s did.”

While she talked her hand was on my dick squeezing and stroking. In less than twenty minutes my soldier was standing a rigid attention. Ruby said, “I had nearly forgotten how quickly a young man recovers. You’re just like Harry was when he young.” While she was stroking my cock I had been sucking and tonguing her massive jug. “Come on baby let’s do it. I’ve waited soooo long and now I want to feel your big, hard cock deep inside me.” Ruby whispered.

This was what I had been working toward for months and I sure as hell wasn’t going pass up the opportunity. Before she could give it a second thought I was between her wide spread thighs and had the head of my pecker at the opening to her cunt. Ruby said, “Pleeeeasssse sweetheart take it nice and slow. It’s been years since Harry died and I want to remember this day for the rest of my life.” I smiled and slipped my cock into her just as slowly as I could. I was surprised, I had expected her old cunt to be sloppy loose, but it wasn’t! Oh it wasn’t as tight as the teenaged girls I had fucked in high school, but none-the-less it was tight enough. I had heard a guy I worked with one summer say two things about a woman’s pussy: first he said that you couldn’t wear one out and second he kidded about a woman having “the pucker string” put in her snatch. I guess Ruby Mathews had had a “pucker string” installed.

When my pecker was completely buried, deep in her old cunt, Ruby said, “Don’t move sweetheart, I want to show you something.” I felt her pussy contract around my dick and then relax only to clasp it again. “How’s that?” She asked. “My God, Ruby, I’ve never felt anything like it.” I said, “Do it again.” Ruby smiled and clamped down on my throbbing prick again. After two or three more repetitions I groaned, “Ohhh baby I just can’t hold still any longer.” The three girls that I had fucked in high school liked it when I used the entire length of my schlong and I there was no reason to think that Ruby wouldn’t enjoy the same thing.

I tried to use long, slow strokes, but it had been so long since I’d had my cock in a nice, hot pussy that I was soon hammering her as hard and as fast as I could. Fortunately, Ruby was even more sex starved than I was and she had at least four orgasms before I cried, “Ohhh shit, I’m gonna cum!” And flooded her hot, juicy pussy with a sea of thick, hot cum.

After my shrunken pecker slipped out of her pussy and we were lying side-by-side she said, “Ohhhh Paul that was just wonderful! God I never thought I’d ever feel like this again.” We cuddled, stroked and petted for fifteen or twenty minutes and then Ruby said, “I don’t know about you, but I could use a sandwich and a cup of coffee, it’s past noon.” We got up, slipped on our underwear, I wore a pair of briefs and Ruby wore only a pair of panties, and went to the kitchen for lunch. While we were eating Ruby said, “I hope you know that you’re sleeping down here with me tonight. In fact you’re sleeping with me every night from now on!” I smiled and nodded my head in agreement. When we finished eating Ruby took my hand in hers and said, “Paul I know that you’ll want to date girls you own age and that’s all right. Just remember, when you get home after a date, you’re still coming to bed with me.”

Damn! What a deal, she was practically giving me permission to date and fuck all the coeds I wanted and was still willing to give me all the sex I wanted from her. How can you pass up a deal like that?

That afternoon and night we fucked three more times and just before we turned off the lights to go to sleep she gave me a fantastic blowjob!

Two weeks later I had my first date with Jeannine Morgan and in less that two months I was fucking her regularly. The funny thing was that, no matter how late I got home, Ruby was always waiting for me. And when we get into bed she insisted that I give her a blow-by-blow account of my date. When I told her about fucking Jeannine Ruby would get so turned on that she would suck my cock until it was as hard as stone and then she’d mount me and ride me long and slow. Sometimes we didn’t go to sleep until three o’clock or later.

Sometimes, when I was upstairs studying, Ruby would come to my room at ten or ten-thirty and we’d wind up sleeping in my room.

Ruby never seemed to lose her desire for a good screwing and, unlike Jeannine; she never had a period, so there was never any “downtime”.

I slept in Ruby Mathews’ bed until I graduated. And when I got my first job, I used the same technique I had used on Ruby on a fifty-seven grandmother of three that worked in my office. I took less than three months to get her into my bed.