The Landlady (Gay Themes)

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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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by maturemaleinmo (edited)

I remember this well, even though it took place almost 40 years ago. It was the summer between my junior and senior years in college. I had not done well the last semester of my junior year, probably because I preferred partying to studying. That, combined with the fact that I would need a couple few extra hours to graduate on time, made it necessary that I attend summer classes. I had always lived in a fraternity house during the normal school year, but in the summer the house was closed down so I had to find a place to stay.

I combed through ads in the local paper and visited a couple of potential places to stay. I finally settled on a room that was being let out by a middle age lady who was a widow. It was nice weather when I looked at the room and I failed to take into account the fact that it was an upstairs room, and would be pretty hot in the summer time. This was back when central air in houses was not all that common. I had to share a bathroom with the widow, but I really didn’t mind that. I found her somewhat attractive, even though she was probably around 42 and I just turned 21.

While chatting with her one day I found out that her husband had died in a car accident a couple of years before, and she just liked to have someone around to talk to, so she rented out this room to college students to help make ends meet. They had not had any children so she was pretty much alone. Her parents were still living but they lived in another state. She worked, as well, so was gone weekdays, during normal business hours.

Summer classes started the first week in June and I concentrated on those, determined to make up for past mistakes. I wasn’t so tempted to party since all of my fraternity brothers were gone for the summer, as were all the girls that I dated. The campus was a pretty quiet place during the summer. I was working a part-time job as an orderly in a local hospital so most of my time was taken up with classes, studying, and work. I didn’t have time to play.

One day I was in a hurry. I had just finished a class and had to be to work shortly. It was a weekday, and I ran into the house to change for work and stormed into the bathroom to take a leak. As I threw open the bathroom door I was startled to find Mrs. Roper, my landlord, soaking in the bathtub. I quickly did an about face apologizing for barging in, but not before I noticed her perky tits and small pert nipples. Mrs. Roper yelled through the door that she would be done shortly. I replied with an okay. I ran on upstairs to get changed. When I came down the bathroom door was open and her bedroom door was closed so I went on into the bathroom and relieved myself. As I left for work I knocked on Mrs. Roper’s bedroom door and told her, through the door, that I was leaving and wouldn’t be back until shortly after 9:00 when my shift ended. All through my shift I couldn’t think about anything except Mrs. Roper’s breasts.

Finally 9:00 rolled around and I punched out and headed back to my room. When I walked into the house through the kitchen door, Mrs. Roper was sitting at the kitchen table dressed in a robe and drinking a glass of wine.

She glanced at me and smiled and said, “Dan, why don’t you sit down and join me for a glass of wine?”

“Okay.” I said, “By the way, I’m really sorry about barging in on you in the bathroom this afternoon. I thought you would still be at work.”

“Oh, that’s not your fault,” she said, “I left work early with a headache, and thought a cool bath might help relieve it. I should have locked the bathroom door I suppose. But, I really didn’t want to.”

I looked at her kind of puzzled as she sat a glass of wine down in front of me. I said, “What do you mean you didn’t want to?”

“Well, Dan, I think we should be a little more at ease with each other,” she said smiling, ” for instance you should call me Ann instead of Mrs. Roper, and another thing is I don’t like having to be so careful not to flaunt my sexuality around you. If you don’t mind, I think we should be a lot more open about our bodies.”

“Open, bodies, what do you mean?” I said and my cock began to stiffen in my pants. I took a sip of wine and was really curious as to where this conversation was going.

“I have something to confess to you, but I have to have your word that you won’t disclose my secret to anyone, no one at all. Do you promise?”

Well, what was I going to say, I was so intrigued I couldn’t say anything but yes.

Before I knew what was happening she stood up and undid her robe and opened it to give me a full view of her body. I starred at it and took in her hourglass shape and her small breasts with the perky nipples and as my eyes wondered on down to her pubic region I noticed a penis, and nearly spit out a mouthful of wine. I just sat there in a trance. I had never seen anything like it before. Finally she closed her robe back up and sat back down.

“I know that isn’t what you expected,” she said, “…but I was born a girl in a boys body. When I was 21 I went to a doctor that specialised in those type of situations, and he took care of me. He began giving me hormones to help me with my body hair which, luckily, was very sparse as it was, and to help me with the curves I needed, to become a female. The doctor and I became very close and eventually married. Yes, my husband who was killed was also my doctor. After a few treatments we started dating, he told me he was bi-sexual and loved what he called ‘transsexuals’.

After a few months we became husband and wife and no one knew that I had once been a male. Luckily I was small in stature and bone structure and my body developed into a nice shape, and my voice changed as I continued taking the hormones. Roger, my husband, eventually found someone who could enlarge my breasts slightly and we had that done, so my transformation was complete, I was a female in all aspects except for one, and that was the fact that I had a penis and no vagina. We lived a wonderful life until Roger was killed in the car accident. Now I have become so horny I don’t know what to do.”

I sat there dumbfounded. My mind was spinning and my cock was stiffening. I’m sure my mouth was open and I was just starring at Ann. The only thing I could think to blurt out was, “How did you have sex?”

Ann smiled and said, “We had wonderful sex, most of the time Roger would fuck me anally. But every once in a while he would want me to fuck him as well, and of course we both enjoyed oral sex.”

“But I’m not a queer,” I said.

“I know you’re not,” Ann said, “…but think of me as a female and not a male. Perhaps that would help.”

“Uh… okay,” I said, “…but you still have a penis.”

“Yes, that I do,” Ann said, “…but I also have breasts.”

“Yes, you do,” I said, “….and lovely breasts they are.”

“See, you’re thinking about them aren’t you?” she said with a smile.

“Yes, I am, but I’m also thinking about the penis,” I said, “why did you tell me all of this and show me your body.”

“I had several boys apply for this room before you, but I just liked the way you looked and the fact that you are shorter and small boned like me. You just appealed to me.” she said. “I guess I was hoping something might come of having you here, and after the incident today, I knew you were too polite to make a pass at me, so I decided to take the bull by the horns.”

“I see, and what is it you want to do with the bull?” I said.

“I’d like you to give me a chance to please you,” she said.

As horny as I was, I was ready to try about anything, but a penis? I didn’t know for sure. My cock was saying one thing and my mind was saying another.

“Well, I need to think about this some,” I said, “…it is quite a shock from my viewpoint.”

“I understand,” Ann said, “…well, the invitation is there if you decide to accept it. And please remember to keep this between us. I certainly don’t want this to get out.”

“Of course,” I said. “I promise to keep the secret and I’m a man of my word. So please don’t worry about that. I really appreciate you being so open with me. I’d better go on to bed. I have a 8:00 class in the morning.”

“Okay, good night,” she said, as I rose, hoping my stiff cock wouldn’t show through my jeans.

I went on upstairs to my room thinking about what had just happened. I had never been propositioned before, by a male or a female let alone a mix of the two. I didn’t know what to do. I undressed and crawled into bed nude as I usually did, but my cock was semi erect just thinking about Ann. I opened a chemistry book and tried to study some but my mind wouldn’t let me. I just kept thinking of Ann’s beautiful breasts, and her little cock. If only she didn’t have that cock, I kept thinking, she would be gorgeous, but then I got to wondering what it would be like to play with it. Does it get hard like mine? Since she had a cock maybe she could suck one better. My mind reeled. What was I to do?

I finally fell into a fitful sleep and dreamed of cocks. Much to my amazement I had a wet dream that night, and didn’t even awaken, but I felt the moistness of the cum in the morning when the alarm went off. I began to wonder if I had just dreamed what I thought had happened last night. I usually ate a quick breakfast at the campus union before class. So I dressed and told myself I would wash the bedding that evening. I meet Ann in the kitchen as she was also getting ready to leave for work. She smiled at me and said, “I hope I didn’t scare you too much last night.”

“So it wasn’t a dream,” I said and smiled back at her.

“No, it wasn’t a dream,” she said, “…keep thinking about my offer.”

That is just what I did all day, think about her offer. I couldn’t concentrate on the lectures because I was thinking about it. I went to the library after class to study. I wasn’t getting much studying done though. Thank goodness it was Friday and I had a weekend to clear my mind. The more I thought about it though the more excited I became and the more my cock throbbed. Okay, I told myself, I’m going to have to do something. I finally decided to take Ann up on her offer, just out of curiosity, of course.

I decided to pick up some items to fix for supper, at the neighbourhood market, on my way back to the house. Friday nights Ann and I usually would concoct some items and share, pot luck style. I got home about an hour before Ann, and I showered and shaved, and then dressed in my jeans and a t-shirt. I was in the kitchen preparing my food when Ann walked in. She looked really nice in a white frilly blouse and dark skirt.

As she passed by me, she told me she was going to freshen up and get into something more comfortable. I got a whiff of her perfume, as she passed, and my cock began to spring into action. I kept thinking of her in female terms. I guess because that helped me to justify what I was about to do. After about 20 minutes she came back into the kitchen in short shorts and a yellow summer pullover with spaghetti string straps. I could tell she didn’t have a bra on as her nipples were causing little points in the blouse.

“Well, have you thought over my offer,” she said.

I didn’t say a word. I turned to her and took her in my arms and kissed her slowly and passionately. I felt her breasts press against my chest as we embraced and kissed for a few minutes. “I guess you have,” she said, as we stopped to breathe. “Let’s celebrate and each have a beer.”

We had a pleasant meal sharing each others food and chatting about our interests. I mostly listened as Ann told me about her life with Roger and their experiences. She told me about the time they had gone to a nude beach in southern France, and about the heads that turned when they strolled down the beach. They both enjoyed the tantalising effect they seemed to have on others, both men and women. My cock continued to pulse as she talked.

Finally supper was over and dishes were done so we decided to get down to business. Ann told me we should use her bedroom since she had a queen size bed and it would be more comfortable for playing. We went into the bedroom, and she told me to get undressed and lay on the bed while she freshened up again. She went into the bath room, and a few minutes later came out in a see through black baby doll negligee that didn’t do much to hide her lovely figure. I had stripped and was laying on the bed with my cock at half staff. When she walked out it came to full erection. The first thing she did was look at it and stare with a mixture of desire and fear.

“What is wrong,” I said.

“It’s quite a bit bigger than Roger’s,” she said looking at my cock.

It is about eight inches fully erect, so it usually gets some attention.

I noticed her small cock protruding though the sheer panties of her negligee. She came over and lowered herself onto the bed beside me. I took her in my arms and we began kissing. I pressed my body up against her, and could feel her breasts, and her now erect cock pressing against me. I’m sure she felt my cock pulsing between us, as well. I slowly removed the top portion of her baby doll negligee and cupped her breasts. I lowered my lips to her nipples and began to suck on them. This really seemed to have an effect on her as she began to moan and writhe. I could feel her nipples stiffen as I sucked. After awhile she rolled me over on my back and said, “Okay, my turn.”

She began by kissing me on the lips and then moved on down my body, past my neck to my nipples and she began to suck on them and I could feel how she must have felt. I’d never really had anyone concentrate on my nipples before, but it really did feel good, and made my cock pulse as she sucked. She didn’t stop there though. She moved her kisses on down across my stomach and on to my cock. She took it in her hand and began to kiss it up and down and paid special attention to the underside. She massaged my balls as her mouth worked on my cock.

Oh my god, it felt so good. After a few minutes of foreplay she took the head into her mouth and I felt her tongue exploring it and caressing it like I had never had anyone do before. Of course, I had only been with a couple of girls so most everything was fairly new to me. She lowered her lips down the shaft about half way and looked up at me with her lovely blue eyes and played her tongue on the bottom of my cock. I was in heaven.

She pulled off of my cock and said, “Your cock is too big for me to take completely, but I’ll do the best I can.”

“You’re doing great,” I said.

Ann explored, kissed, and caressed my cock and balls for almost 10 minutes and then I couldn’t hold my orgasm any longer. I told her I was going to cum, and she buried her mouth onto my cock as far as she could get it and I shot my cum down her throat. She swallowed quickly and must have sucked while I came, because I had the most intense orgasm I had ever had. I completely relaxed after I came and she moved up the bed a little to lay burrowed beside me with her breast on my chest and her head on my shoulder. After I had come back down to earth, I told her that was the best orgasm I had ever had. I could feel, more than see, her smile and she said she was glad I enjoyed it.

“How was it that you made me cum so hard,” I asked.

“I just suck slightly as you cum,” she said, “…and it intensifies the orgasm. It is something Roger taught me.”

“How can you swallow my cum,” I asked, “…doesn’t it taste bad?”

“No, not at all,” she said, “…as a matter of fact it is quite tasty.”

Then she proceeded to move up and give me a kiss and she ran her tongue into my mouth. I was surprised but I could also slightly taste a mild salty flavour in her kiss. “See, that doesn’t taste bad, does it?”, she said and smiled at me as I realised I had just tasted my own cum.

“No, it really didn’t,” I said.

We started talking about the things that turn us on, and Ann admitted that she loves being sucked off as well. Oh boy, that puts me on the spot. I’d never even felt another penis, let alone sucked one before.

She sprang to life and said, “Okay, it’s my turn now,” as she slipped out of her black see through panties and straddled my stomach.

I looked up at her and marvelled at her beauty. She really was a lovely sight, sitting there with her dark hair and perky breasts, with their pert nipples, and her feminine figure and her cock and balls laying out there on my stomach. Her soft cock looked tiny about 2 inches at the most I guess. It was completely shaven so it kind of looked like a boys dick. I just starred up at her and then at it.

Finally she said smiling, “Go ahead just touch it. It won’t bite you.”

I moved my hand up and put a couple of fingers on her cock. It stiffened a little and I quickly pulled back. Ann laughed at my reaction. I touched it again and it felt a lot like mine. I pressed it down on my stomach and I could feel it’s warmth. Ann raised up on her knees some so that her cock hung loose between her legs and I could grasp it. I did just that and it felt pleasant, really kind of exciting. I stroked it a few strokes and she began to stiffen.

“Are you ready,” Ann asked.

“I guess so, as ready as I’ll ever be,” I said.

She walked on her knees up toward my face until her cock was right in front of my face. I noticed a small drop of pre cum on her slit and I stuck my tongue out to lick it off. Start with baby steps I thought. I began kissing her cock and then before I knew it I had it buried in my mouth. It actually felt very sexy. I can’t really explain it, but I didn’t feel like it was wrong. It just felt warm and stiff and right.

She was moving her cock in and out of my mouth like she was fucking it. I could take the whole thing into my mouth and while she did it grew hard to a thickish four inches. Suddenly she pushed into my mouth hard and I felt, more than tasted, her hot cum hit the back of my throat. I tried to suck but it took me by surprise and I just let things flow unscripted. She held onto the headboard while she orgasmed. I thought what a turn on this was, seeing her above me like this in the throws of orgasm. I marvelled at her erect nipples, the look of pleasure on her face, and her cock buried in my mouth shooting her cum down my throat. I was actually getting erect again. I couldn’t believe this.

Finally she slipped her cock out of my mouth and slid down my body and leaned over and kissed me probing her tongue into my mouth lapping up what cum she could still taste. My cock was now stiff as a board and pushing into her butt as she straddled me.

“Oh my, you’re randy tonight,” she teased as she reached back and caressed my cock, pushing it between her butt crack. “Are you ready for more?” she asked.

“I’m game,” I said. “I can’t believe how much fun this is.”

“Okay, let’s proceed with our lessons then,” she said with a sexy smile. “You’ll have to let me be on top for this one though. It’s been a while since I have fucked, and with your big cock I need to proceed slowly.”

She reached over onto the night stand and picked up a bottle. She said it was a lubricant and she proceeded to pour some in her hand. She then stroked my cock with it, and reached behind her butt and apparently put some in her anus. She then straddled me again and took my erect cock and positioned her butt over it. Then I could feel her lower herself down onto my cock. I felt the head of my cock slip into her hole as she slowly and deliberately slid my cock up into her anus. I watched her face and some of the contortions she was making.

It seemed like that had to hurt, but since I was on the receiving end it felt good to me. I had never felt a pussy as tight as her ass was. After a few minutes she had engulfed my cock completely. I was again in ecstasy. She slowly started to slide up and down on my cock. I could feel the warmth wrap around it and the friction of the tightness, as she slowly fucked me. I watched her cock and balls bounce in front of her as she rode my cock, now getting faster and faster. It wasn’t too long before I felt another orgasm coming on. I wasn’t sure what she wanted to do. I quietly said I was about to cum again, and she increased her motion some. Finally I felt the rush of orgasm, and I pushed up into her butt.

She pushed back taking it as deep as it would go and I shot my wad into her hot ass hole. We froze in that coupled pose for a few seconds as I finished cumming, then she collapsed on top of me. Both of us drained of energy from our exertion. My cock stayed buried in her fuck hole as she squeezed every last drop of my cum out of it. Finally it softened and slipped out. I could feel my cum dripping out of her pussy onto my pubic area. God, it was so sexy. I couldn’t believe I had had misgivings about this relationship. We kissed and cuddled and eventually drifted off to sleep both exhausted.

I awoke as the sun broke through the bedroom curtains. I was snuggled up against Ann in a spoon position, with my naked cock snuggled into the crack of her buttocks. I felt it pulse as I thought about her, and our experiences last night. My arm was over her and I gently fondled one of her breasts. She stirred.

“Mmmmm, aren’t you even going to let a girl get her beauty sleep,” she said, as she rolled over and kissed me.

“Wait,” I said, “I have to go brush my teeth.”

She laughed and replied, “Me too.”

We both got up and went into the bathroom. Ann sat on the toilet while I grabbed my tooth brush and applied some tooth paste and began brushing. I noticed her put her hand between her legs and then I heard her begin to pee.

“My penis is so small that sometimes I pee over the edge of the toilet bowl if I don’t hold it down,” she said smiling. When she finished she got her tooth brush and began to brush her teeth while I raised the toilet seat and peed into the bowl.

“You certainly make a lot of noise when you pee,” she said, “…now I know what they mean by a horse pissing on a rock.”

I was perfectly comfortable performing in front of Ann. It is amazing what a little sex can do to lower self imposed barriers. “How about showering together,” Ann said, “…wouldn’t that be fun.”

I quickly agreed and she turned on the shower. We climbed into the shower and began lathering each other down. I decided not to use a wash cloth as I soaped Ann’s body. I enjoyed the feel of her soft feminine skin and wanted to feel her whole body. I didn’t even hesitate when I got to her cock and soaped it and gently massaged it as she began to stiffen. “Oh, you certainly know how to turn me on,” she said, as I stroked her now hard little cock.

Since she kept her pubic area shaved it felt soft and smooth. It was a real turn on for me, and my cock began to harden also. “I can’t believe how readily I have fallen into enjoying another penis,” I said amazed, “…it’s as if I have doing this all my life.”

“You have, but with your own penis,” she teased.

I lowered myself to my knees and let the warm water run over my head, as I took her cock into my mouth and began to suck on it. It felt so good. It was beyond thrilling. I think it was as good sucking hers, as it was having her suck mine, well, almost anyway. I moved my head back and forth and felt the head of her cock push against my throat. After a few minutes she came. I swallowed every last drop of her delicious cum. I was developing a taste for this.

I stood and it was her turn to lather me. She too used her hands and soaped down my entire body. She rubbed my chest and then my back and eventually we were embraced in a passionate kiss as she moved her hands down to my butt. I could feel her cock pressing against mine as we embraced and her left hand applying soap while her right hand rubbed. All of the sudden I felt her finger entering my anus and I gasped.

I pulled my face away from hers and said, “What do you think you’re doing?”

“I’m just cleaning you up, Danny. What’s good for the goose is good for the gander,” she said and smiled.

Well this wasn’t something that I had planned on, but it did feel kind of good when she pushed her finger up into my anus. I agreed and she began to wash me again, this time pushing it even further into my ass hole. At least she has a small penis I thought.

As we got out of the shower and towelled each other we continued to kiss and fondle. It was just hard for us to keep our hands off of each other. Ann reached into the under sink cabinet and pulled out a box, and opened it, pulling out a rubber bulb like thing with a small hose on it.

“What is that for,” I asked, knowing good and well what it was for.

“Part of sex is being squeaky clean,” she said, “…and that includes your anus. This is to get it good and clean for me.”

“I’ve never had an enema before,” I said nervously.

“Don’t worry it doesn’t hurt, and it won’t be much of one. We just need to get the lower portion of your pussy clean.”

Pussy I thought. Fuck me, I hope none of the guys find out about this. But now I was actually anticipating with excitement the thought of her giving me an enema. She told me to lay down on the bath rug on my side and to put my top leg over my bottom leg so that my anus would be exposed to her. She filled the bulb with water and attached the hose and then put some lubricant on it and some lubricant on her finger. I felt her finger press against my anus lips and then enter smoothly as she applied the lubricant.

My cock was responding in a rigid manner as she played with my ass hole. Next she placed the end of the hose into my anus and squeezed it and I felt cool water shooting into me. It was exhilarating. She emptied the bulb and then told me to empty my pussy. So I got up and sat on the toilet and sprayed out the water she had just put in.

“One more time, just to be sure,” she said. So I laid back down and assumed the position while we went through the same process.

“See, that wasn’t bad, was it?” she said, and I replied that it was actually quite exciting as exhibited by my erect cock.

She took my hand and led me into the bedroom, and then told me to lay down on my back it was time for me to loose my virginity. Oh boy, I thought what was I getting into. She crawled up onto the bed and positioned herself between my legs and she lifted them up so she had easy access to my butt. She took some more lubricant and placed it in my anus and then stroked her now rigid cock with it as well.

“Don’t worry, I’ll be gentle,” she said, “…let me know if it starts to hurt.”

I felt the head of her cock push against my anus and then slowly start to enter. I guess I was unconsciously tightening my butt against the intrusion because she told me to relax and let her get past my sphincter muscle. I did what she said and I felt her slip in. It hurt for a second but was quickly forgotten when I felt her cock buried in my ass hole. There was something unbelievably sensual about it, and my cock again sprang up for the occasion. She at first just held her cock in there to get me accustomed to it.

Then she began to slowly move it in and out. What an exhilarating feeling it was. I was ignorant about the prostrate at that young age, but now I know it has something to do with massaging that male organ. As she moved in and out of my ass hole she grabbed my cock and began to stroke it. I watched, completely enthralled with the whole erotic experience, her tits bouncing and her stroking my unbelievably hard cock, while I felt her cock moving in and out of my ass. It really wasn’t long before I came and came and came. I shot a wad of cum all the way up to my face. It actually hit my chin and I licked it. Ann was right it did taste good. I was becoming addicted.

Suddenly I felt Ann push her crotch into my ass and I felt her cock begin to throb in my anus, as she shot her load of hot cum into me. After she completed her orgasm she lay down on my chest, keeping her cock buried in my ass and kissed me. I felt my cum that was spread across my chest ooze between us, and we kissed and held each other. I think I am falling in love.

I was very glad today was Saturday, that would give us the whole weekend to play with each other. But then, why worry, we had the whole summer to play. No telling where this adventure might lead.


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