A College Education

When I returned to the University in the Fall I was determined to find a place to live off Campus. I was in a Dorm my first year and it was a disaster. The constant noise, the party boys, the pranks and immature nonsense drove me crazy. I am in school to study and do well, and not see how much beer I can drink.
I found some ads for rooms on the internet and started to investigate. The first five places were terrible; the houses were run-down shacks and the rooms were not fit for human habitation. I have a limited budget but I will not live like that.
I did not want to give up so I called the number for an ad that seemed promising. A warm and soft feminine voice answered, and I made an appointment to see the room right away. I punched the address into my GPS and headed out.
As I was driving I tried to visualize the woman behind the voice. I pictured a hot young sex-crazed blonde waiting to meet me.
What am I thinking? I need a room; I don’t need to get laid. Well, actually that would be great, but get real. Grow up, don’t let your imagination get out of hand.
I pulled up to the house and parked in the driveway. This was more like it, a beautiful old Tudor style house on a landscaped lot.
I rang the front door bell and waited, and when the door opened a tall, stylishly dressed woman said hello. Not exactly a hot young blonde, but very attractive. I guessed maybe she was in her forties, slender and fit, and a beautiful smile.
She was dressed in designer jeans, not the cheap kind that I had on. She also had on a colorful top which I won’t try to describe because I am not a fashion maven. Her shoes completed the ensemble, and she looked marvelous.
She introduced herself as Dorothy Johnson and shook my hand. Very courteous and old-school.
“I am William Lee. I am a second-year student and interested in a room off-campus. I can’t tolerate the Dorm again.”
She laughed at that and said “Please come in.”
We walked through the front hall and into the nicely furnished living room.
“Please sit and be comfortable. Tell me about yourself.”
I launched into my rehearsed bio; from a small town, serious student, etc., in Pre-Med.
“Well, you seem like a very nice young man, just the kind of person I would like to have in my spare room. This house was built back in the day when people had live-in domestic help, and the room in question was the room for that person.”
“My husband passed away a little over a year ago. When he was alive he would offer the room to visiting VIP’s or sometimes to students who wanted to get away from the distractions, just like you. There was frequently someone interesting staying here for short visits. In the past year, it has not been used at all, so I thought it would be a good thing to offer it to someone deserving.”
“I thought I should ask for rent, just to make things legal and correct. But mainly I don’t want the room to continue to go to waste.”
I replied “Mrs. Johnson, that is very kind of you.”
She came right back with “Please call me Dorothy. I am not that old!” and smiled.
“So now that we have discussed all of that, let’s have a look at the room.”
She led me to the stairway that must go to the spare room and I followed her up. I was just a few stairs behind her, and her ass was right in front of my face. Her ass was beautiful, not too large or too small, and her tight jeans accentuated her butt crack.
All I could think of was what she must look like naked, and then I told myself to stop it, she is a refined, upper class woman and not like the fuck-sluts you meet around the campus.
We got to the room, and it was very nice. Much larger than I expected, and nicely furnished with a double bed.
“It also has its own private entrance, that stairway over there leads to a door in the rear of the house.”
God, please don’t say rear, I can’t get my mind off yours.
“I keep that door locked, but I would give you the key if you want it. I really prefer that you come and go through the front door and go up the stairs we just used. I want you to feel comfortable and at home in the entire house. I don’t want you to be a hermit.”
“There is a microwave and a small refrigerator, but I hope you can join me for some meals. I love to cook and cooking for a single portion is difficult. And I would enjoy the company. There is also a private bath, just a shower but that is probably what you want anyway.”
Now we got to the bottom line and she said “I was thinking of $400.00 per month. Is that OK?”
That was beyond my budget, and I didn’t know what to say. I followed her down the stairs, this time with a different view of her beautiful ass.
We were standing in the hallway by the stairs and by her bedroom door, and she was waiting for me to reply.
“Mrs. Johnson, you have a beautiful home, and the spare room is great, but I just can’t afford it.”
She seemed very upset by that, and said “Please call me Dorothy as I asked. I don’t know what the rental rates are near the campus, I just made a guess. I don’t want you to leave, I want to work something out.”
“The money is not as important to me as having the right kind of person in the room. My husband left me in very good financial condition.”
“Maybe there is something I can do for you on the rent if you would do something for me.”
She seemed quite nervous and uncomfortable so I said “Sure. Just tell me what you want.”
“I was really hoping for some companionship and company. As I said, my husband died just over a year ago, and we had a long and wonderful marriage. Since then I have become a kind of recluse. I rarely leave the house except for tennis at my club or grocery shopping. Being alone in this big house is not healthy.”
I was not ready for what came next.
“I can reduce the rent if you would do something very personal for me.”
She would not make eye contact with me, she just stared at the floor.
“Like I said, just tell me what you want.”
In a voice so low I could barely hear her, she said “Would you be willing to hook up with me?”
I would not have been more surprised if she threw a bucket of water in my face. I was speechless and she must have thought that I didn’t understand her.
“That is the term that young people use now, isn’t it?”
I replied “No, I usually just say fuck.”
She actually flinched at the word, but she managed to say it almost in a whisper.
“I see. Then would you be willing to fuck me?”
After a few moments of awkward silence, I said “Really? Right here? Now?”
Her face was beet red as she stammered “No. I mean that would be nice, but no, I meant on a somewhat regular basis.”
I was silent, so she said “Look, I should not have just blurted that out. You are embarrassed and I am humiliated. I just didn’t want to lose you. Of all the people who have inquired about the room, you are the only one I want in my house. I can explain everything, but it will take a while. I realize that I am more than twice your age, but I don’t think having sex with me will be unpleasant for you.”
“Let me get this straight. You will rent me the room at a lower rate if I have sex with you? What, every day, or every week or what?”
She answered “No, I am not trying to make it a quid-pro-quo kind of thing. I just meant that we could be nice to each other when we both felt like it. I am not trying to enslave you.”
Bear in mind that this was not some old hag; Dorothy is a very attractive mature woman. She is slim and trim, with grey hair but in the fashion of today where many women choose not to color it. The only word I can think of to describe her is elegant.
She said “I realize that it looks like I lured you here and I guess in a way I did. But I do crave the companionship and the company. And I have to admit I crave sex. I haven’t been near a man since my husband died, and before that it was 30 years with only him. I am growing older, and before I know it my chances will have passed me by.”
“I don’t want to go out to clubs and try to get picked up by some guy who might turn out to be a creep. The men I know as friends are all associates of my deceased husband on the faculty. I can’t have an affair with any of them, and they are all much older than me and probably not interested or even capable.”
“Would $200 per month be within your budget?”
She stood awkwardly and averted her eyes. She was trembling and obviously uncomfortable and looked like she might burst into tears.
I finally realized that I was not imagining this, it was real and the opportunity of a lifetime.
“Dorothy, you do not need to be embarrassed or ashamed. I am not offended in the least.”
I moved close to her and she melted into my arms. I get a hard-on at the worst times, but this was a good time. It started to stiffen and grow, and soon there was a large bulge in my underwear. I pressed it against her and I was sure she felt it because she reacted to it
She backed away a little and looked at the mountainous shape of my cock. She stared intently at it in deep thought.
She was blushing and obviously conflicted. She didn’t want to be rude but she couldn’t take her eyes away from it.
“I should not have done this, not in this way. I am so inept, I don’t know how talk to a man to begin a relationship. I feel like a fool.”
“Dorothy, please don’t feel that way. I am not uncomfortable at all with you. Just say and do whatever you wish.”
Ever polite, she asked “May I touch?”
“Of course, please do.”
She moved closer and tentatively reached out and touched my cock though my jeans. She explored the length of it and squeezed it gently.
I decided to help so I pulled my jeans and underwear down and my stiff cock sprang out.
She stepped back. It seemed like she didn’t know what to do or say. She averted her eyes modestly, but then she was drawn back to my stiff hard-on. She stared at it, then looked away, then stared again.
“Can I touch it again, now that it is out?”
“Sure, why not.” I took her hand and guided it to my cock, and she caressed and stroked it.
She seemed uncomfortable again, and said “There is something else you need to know about me. I am fifty years old, and you may not know this about women of that age, but sex has become difficult for me. Painful, actually.”
I said “Do you just do oral then?” because I thought that was what she meant.
“No, not that. I can show you what I mean if you will let me.”
I nodded my head and she led me toward her bedroom down the hall. I had to pull up my jeans and underwear to walk.
When we were next to her bed I pulled them down and completely off. She undressed like she was in a changing room at the mall, trying on clothes. She pulled off her designer jeans and slipped her blouse over her head. She undid her bra and revealed her perfect tits, not too large and not too small, just right. Then for the best part – she pulled her sexy panties down and over one foot, and tossed them aside.
She laid everything neatly on a chair next to the bed, and nervously gazed at the wall or the floor, anywhere but at me. She stood in front of me completely naked but she tried to modestly cover her pussy with one hand. What she couldn’t cover up was her magnificent ass and her long legs leading up to it.
She stood there in a self-conscious way and tried unsuccessfully to keep her eyes from my stiff hard-on. Why is she suddenly so modest and shy? She just came right out and asked me to fuck her a little while ago.
She softly said “I have never done anything like this before, and I am feeling awkward being naked with you.”
As I said before there is not an ounce of fat on her body. Her legs are long and toned, and her ass is smooth and silky. Her pubic hair is as gray as the hair on her head, and there is enough clearance between her thighs for me to see her butt cheeks from the front.
“Don’t feel that way. You are incredibly beautiful and you should be proud of your body.”
She took my hand and indicated that we should lay down. She was completely naked so I quickly stripped off my shirt, shoes and socks. We got on the bed side-by-side.
“Let me show you what we need to do.” She took a tube of what must be lube from the night stand drawer and greased up my stiff hard-on. I thought that was to take care of her vaginal dryness, but when I made a move to line my cock up for that she stopped me.
She was on her back with her legs drawn up and I got on my knees between her legs. Her vagina was a tightly closed slit. She grasped my slippery cock and guided it to asshole.
She closed her eyes and whispered “Please. Do it this way.”
This was something I had never done but always fantasized about. I had unsuccessfully tried to do anal with two of my girlfriends. I tried to finger one girl’s asshole when I was fucking her but she said “What are you doing down there? Stop it!” I almost got my cock up another girl’s asshole but when just the tip went in she screamed and said “You pervert!” She got up and got dressed and that was the last time I saw her.
Now I not only had a woman who was willing, but was asking me to sodomize her. If this was a dream I didn’t want it to end.
I hesitated and said “Have you done this before?”
In a whisper so low I could barely hear she said “Yes. My husband taught me after I couldn’t have sex vaginally.”
OK, I thought, here goes. The head of my cock was against her asshole and I pushed it in.
She flinched and yelped so I stopped. Fucking a woman anally has been a favorite fantasy of mine but I didn’t want to hurt her. She did say she had done this before, right?
“Are you alright?”
“Yes. Please don’t stop. It’s OK.”
I pushed a couple more inches in and she made eye contact with me and gave me a sweet smile.
Her asshole was twice as tight as the youngest pussy my cock had ever been in, especially right at the entrance. It was soft and warm inside her, but the ring of her anus gripped me like a rubber band.
I carefully kept pushing, and when I was almost half-way in her expression changed. I pushed another inch in and the look in her eyes was priceless, a combination of disbelief, curiosity, apprehension, and arousal.
She said “I think that’s far enough.”
“I don’t. Hold still.”
My cock continued to insinuate itself deeper and deeper up her asshole. She looked into my eyes with a wide-eyed stare.
“I don’t believe this!”
I whispered “Don’t you want it all the way in?”
She took a deep breath and said “No. Please. I am afraid. Just do it to me with that much.” So polite.
She had a dreamy expression on her face, and her eyes were partly closed. She adjusted her position slightly to get more comfortable, I guess. I tried to push it in and out without going in any deeper. Her eyes went wide open with a look of surprise and bewilderment.
“It keeps going in farther each time you push!”
What did you expect, I thought but did not say. I have over nine inches so even half of it is going to go pretty deep. But why is she so surprised? She said this wasn’t her first time. It was my first time, however, and the sensation of being buried in her soft insides was fantastic.
I kept fucking her gently since I didn’t know how much movement she could take or would want. The tight ring at the entrance to her asshole felt just like my masturbation technique, with my thumb and forefinger encircling my cock tightly and sliding from the tip to the base.
She made whimpering, murmuring sounds as my cock slid in and out of her, and I was sure they were sounds of pleasure and not pain.
I was so turned on I couldn’t hold back; the old idea of thinking about baseball doesn’t work for me.
I pushed as far into her as I dared and ejaculated so hard I thought my balls might shoot out of my cock.
Dorothy gazed lovingly into my eyes and whispered “Yes.”
I huffed and puffed and tried to catch my breath, and she affectionately caressed my face, my shoulders, and my back with a light feminine touch.
We stayed together that way for a minute or two, and then I pulled my still hard cock out of her. I moved away from my position hovering over her, and lay down by her side. My cock was glistening with creamy cum, and still standing up.
“I am sorry that I was so quick. I was just so turned on that I couldn’t hold back.”
“Don’t be sorry. I think that is quite normal for a man your age. It was nice for me.”
She got up and went into the bathroom, and returned with a warm wet washcloth. She wiped my cock with it, but I don’t think there was anything to clean off except the extra cum clinging to it. I guess she was just being sure.
She snuggled up to me and cuddled like a teenager in love. She kissed me and said “That was not too bad, was it? Would you be willing to do that once in a while to make an older woman happy?”
“Dorothy, I will do that to you every day, as many times as you want me to. Is there a bell you can ring in the room to summon me?”
That got a laugh out of her, and she said “No, silly, you are not my sex slave. And you can be the one to initiate things too, if you want to. I will never say no. I will always be available to you.”
“I was afraid that I was hurting you. Was I?”
“Just a little right at first. I got used to it and then it was fine.”
She blushed again, and said “I don’t know how to talk about things like this. You are much larger than my Husband was. Longer and thicker. I had no idea about this, I have led a sheltered life, I guess.”
“I was amazed at how far it went into me.”
And then she buried her face in the bed sheets, embarrassed about talking about the size of my penis and how it felt inside her.
After we rested a while we got up and got dressed. I went out to my car to bring in my clothes and what little else I brought with me. As I carried it to the stairway she called out from the kitchen “Make yourself at home.”
I did just that, hanging some clothes and putting some in the dresser. I laid down on the bed and relaxed, and thought about my good fortune. This is a great room, and I am getting it for a very low price provided I fuck the landlady up the ass occasionally. I think I can handle that.
I thought back on how it felt, and my always interested cock got hard. I pulled my jeans and underwear down, and it stood up and looked at me with its one eye. God, it never gets enough.
I considered jacking off, but then I wondered if she really meant anytime was fine with her. I decided to find out (or I guess my cock decided for me).
I pulled up my jeans and headed down the stairway. I called out “Dorothy, are you still in the kitchen?”
I heard her muffled reply coming from her bedroom. I went right in and caught her in the act of masturbating, completely naked.
“Let me help you with that” and I quickly got on the bed next to her. I kissed and licked her pussy, and flicked her hard little clit with the tip of my tongue. In about 30 seconds she had an intense orgasm.
I wanted to see how far I could get my tongue into her, but her dry tight cunt made it impossible. Oh well, she seemed satisfied so I hugged and caressed her.
“I was so hot and bothered after you fucked me I had to do something.”
I made a mental note to make sure she was satisfied whenever I finished fucking her.
“No worries,” I said and pulled off my jeans. My cock sprang out, and she playfully said in a little girl’s voice “Oh, is that for me?”
“Yes, and this time please turn over.”
“I will, but I need to say something first. It was unfair of me to stop you. I want you to keep going unless it really hurts. I will tell you if it does.”
She turned over, and reached back to spread her butt cheeks for me. Right above her dry cunt slit her pink asshole was in plain sight. She lifted her hips up, offering it to me. I accepted.
My cock went in a little easier this time, and she didn’t act surprised by how it felt. I worked it in a fraction of an inch at a time.
We didn’t use any of the lube and she didn’t seem to mind. I actually liked it better because of the tightness and the resistance and she didn’t complain. The only way she reacted was with a muffled grunt each time it slid in a little.