Denny As The Handy Man Ch. 2

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Denny takes advantage of a lonely tenant.
9.7k words
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188.4k
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Part 1 of the 2 part series

Updated 10/03/2022
Created 07/17/2001
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denny9
denny9
656 Followers

Once again I had been denied a chance to look good in Maggie's eyes. The fact that she was a stripper just made me all the more desirous of her. I still wanted to make love to her but I still hadn't found a way to impress her. At least now I had a release for my pent up hormones in the older tenant, Mrs. Johnston and she was even willing to pay me for my 'services'. A couple more 'house calls' as the handyman and I at least would have enough money to go after Maggie at the Fantasia Club.

Another woman in the rooming house that caught my attention was Mrs. O'Brien who lived in 2B with her two young sons, Bert and Ernie. I know it sounds funny but that's what their names were. Really! They were 11 and 12 years old and into sports. Me, although I was more into 'indoor sports', had been known to be not a bad tennis player.

Mr. O'Brien was in the navy and was away at sea for a six month stint so I scored big points with their 34 year old mother by helping the boys improve their games while Dad was away. Mrs. O'Brien was an average looking woman with short brown hair to go along with her petite size. She was only around five foot two and she actually did have 'eyes of blue'. More importantly she seemed like a likely target for my sexual needs. I set about trying to get into her pants.

After every lesson with the boys I made sure that I praised them to the hilt. Typically she would want to hear more and I started to get invites for soda and finally dinner. The boys of course never wanted to stay around after dinner so they would head out to their friend's houses leaving me to help Mrs. O'Brien to clean up.

I did everything I could to look good in the young mother's eyes. I would compliment her on her cooking and moved from there into congratulating her on what fine boys she was raising basically on her own and that it must be very difficult. After a couple of such occasions I noticed that she started to dress differently. She started to wear make-up and obviously had fixed her hair into a cute pixie cut which I quite liked and which certainly suited her face.

One morning when I arrived to pick up the boys, Mrs. O'Brien opened the door and she was still in her nightgown. Standing with sunlight behind her I could see her petite figure right through the translucent material and immediately got a hard-on. I didn't try to hide it. In fact, I hoped that she would notice it, which she did. I caught her looking down at the front of my tennis shorts and she got all embarrassed when she looked up to see me observing her.

Trying to regroup, she muttered that the boys had gone to their grandparents for the weekend and she apologized for not letting me know but it had just come up at the last moment. I guess I looked disappointed because she apologized profusely once again and slowly started to close the door.

Panicking, I scrambled for an idea to try to take advantage of the situation. I realized that I might not get another opportunity like this. Suddenly a brainstorm hit me.

"Remember you asked me to fix the screens in your apartment. Well, I could do them now if I wouldn't be disturbing you. " I held my breath hoping that I hadn't been too obvious as Mrs. O'Brien pondered the situation.

Smurking as though she knew my intent, the lonely tenant gave me her approval. "Okay, Dennis. I'll get dressed while you get any tools you might need. " Of course, I was hoping that I would only need one tool and I had it with me at all times.

I was back in a flash and Mrs. O'Brien hid behind the door and said shyly, "Boy that was quick. Do you do everything that fast?" I wondered if she had meant it as a double-entendre the way I had interpreted it. "I'm not quite dressed but I suppose you could come in and work in the living room while I finish changing. "

Trying to integrate some humour into the rapidly heating up scenario, I joked "Okay, Mrs. O'Brien. Close your eyes 'cause I'm coming through. " With that I stepped through the doorway and walked over to the window. Because the shades now were closed (hadn't they been open previously?) I could see the reflection of Mrs. O'Brien in the darkened window as she quickly dashed into her bedroom. I was pleasantly surprised to see that she had replaced her nightgown with a set of matching black undies – low cut bra and thong panties.

My cock pulsed in appreciation. She was more attractive than I had given her credit for or perhaps my rising libido didn't have such high standards of beauty. I tried to divert my attention from her long enough to attend to the loose screen. Fortunately it only required a minor adjustment.

I was surprised, however, when upon completing the minor task, I turned and saw my hostess once again appraising me. This time her eyes were zeroing in on my butt. Again she was red-faced when she realized that she had been caught. This time neither of us averted our eyes for what seemed like minutes but was probably only a few seconds.

"I…I…I'll make coffee while…you…fix…the…the…bedroom…ah.. while you fix the bedroom screen. Okay?" she stammered but her embarrassment was really about her emphasis on the word 'screen' and she quickly fled into the small kitchenette.

Now it was my turn to smile smugly as I watched her cute butt disappear. I love women in tight tank tops and short skirts and she had the figure to show off in both. Once again my raunchy organ raised its head in appreciation.

Entering the foreign territory of her bedroom, I was impressed by the feminity of the room. It was obvious that there was no male around to mess it up. Indeed the only sign of a male was the picture on the dresser of Mr. O'Brien in full dress naval uniform. The bed was made and there were no clothes lying around like in my bedroom. Hearing the kettle whistle, I realized that I better at least pretend to be doing the screen and it was a good thing I did too because this one was tougher.

Minutes later, Mrs. O'Brien entered the bedroom carrying my mug of coffee and she hesitantly brought it over to where I was positioned between her bed and the window. As she started to pass it to me she tripped over my toolbox and sprayed the steaming hot coffee all over my shirt.

"Ow.. it's burning!" I cried and started to tear my stained t-shirt off over my head.

"Oh my god! I'm so sorry, Dennis! I'll get some ice to put on the burns!" With that she raced out of the bedroom.

Within seconds she had returned and started to rub the ice cubes which were wrapped in a tea towel over my damp chest. As she apologized over and over, she hadn't realized that we were now sitting side by side on her bed but I knew that this was my golden opportunity and I intended to take advantage of it.

As she applied the wet towel to my chest and implored me to forgive her, I placed my hand over hers and helped her guide the compress lower. My stomach had a couple of red blotches from the hot coffee and I hoped to use them to further my plan. Knowing what I was hoping to accomplish, my body forgot any prior pain and my cock was now extended past the tip of my shorts. The outline of the shaft could not be missed.

I drew her hand over it and waited for a reaction. She ran the cloth over the showcased organ and it was like she wasn't even aware what she was doing. She passed the wet cloth all along its full length and back again. My groans finally awakened her to what she was doing.

"Oh…my.. I'm so sorry, Dennis! I don't know what came over me. I'm so embarrassed. Please forgive me. "

Before she could withdraw her hand completely, I held it in place and encouraged her to continue. Slowly she started to trace the outline of my engorged cock with her fingertips until she finally touched the tip which was barely jutting out past the edge of my shorts. Her free hand reached the tab of my zipper and started to pull it down which freed my organ into the early morning air. Up it stood proudly and she gasped. I then took her hand and placed it around my shaft and encouraged her to continue.

"Please, Mrs. O'Brien, don't stop. It feels so good!"

It was like she was in a daze. She gently pulled the foreskin back and said, "It's so big. I've never seen an uncircumsized one before. Does it hurt when I do this?" Gently she rolled the skin back to expose the glans and then rolled it back over the head. Drops of pre-cum were already forming at the slit.

I took an ice cube and started to caress her neck with it. Sliding it back and forth. I made my way to the tops of her breasts. Smoothly I helped her pull the restraining top over her short curly hair exposing her heaving breasts to my gaze. Taking an unmelted cube I wiped it back and forth over the skin that rose above her half bra and finally placed it on her nipple. She gasped softly as I then moved to her other nipple and repeated the exercise.

Undoing the clasp I finally pulled the bra off and placed the cups of both my hands over the untanned orbs and started to tease the nipples. Next I leaned forward and placed my mouth over her right breast and started to kiss from one to the other. While doing this my hands were busy reaching under her short skirt and stroking her womanhood. She raised her hips to accommodate the removal of her black thong panties and pulled her skirt up above her waist. She was totally exposed now and I started to kiss my way down to her honey pot.

She stopped me as soon as my tongue started to lick her clitoris. "No, Dennis! Don't do that! It's dirty! No one's ever done that to me! Please don't! Oh my god.. that…that feels so.. so good.. oh.. Dennis.. oh don't!"

Her resistance was weak however and she soon gave in to the pleasures that started to wrack her body. Soon my tongue was alternating with my fingers as they took turns invading her pussy and she started to breathe heavily. Faster and faster I started to slobber over her clit while driving my fingers deeper and deeper. Grasping my hair, the mother of my tennis protegees, pulled my face flush into her pelvis and started to hump her mons at my face. It didn't take long for her to cum and she arched her back screaming, "Suck me Michael! Suck my cunt! Make me cum! Don't stop! Oh.. Michael! I'm cumming!!"

Suddenly her body was wracked with violent spasms and I just held on for dear life ignoring the fact that she had called out her husband's name in the middle of her orgasm. Hardly missing a beat she implored me to fuck her. Fuck her hard and fuck her now. She rolled onto her back and pulled me up between her spread-eagled legs.

Looking into my face, she pleaded, "Fuck me Mi.. " but she caught herself this time. "Fuck me Dennis! Stick that young cock in my cunt! It's been so long! I need your prick in me! Make me cum!"

Grasping her legs, I worked them up and over my shoulders and started driving my shaft deeper and deeper into her. The noise from the slapping of my balls against her ass was only concealed by the loud squeeking of the bed springs. Faster and faster we drove against each other neither one of us relenting until we reached our climaxes together. The familiar warmth which warned of my impending eruption was rising in my testes. Her heels locked around my neck as she spasmed again.

Suddenly she placed her hands on my shoulders and pleaded with me to stop. Impossibly she halted her hip movement as well while I continued to try to plunge on relentlessly.

"Please, Denny! Don't cum in me! I'm not protected! Please pull it out before you cum! You can cum on me or in my mouth but please I'm begging you don't cum in me! I can't get pregnant while Michael's at sea. Please!"

It took every ounce of self-control that I possessed but I was able to pull out just as I was starting to erupt and the first jet of cum shot up onto her belly and over her breasts. Quickly moving up her body, I aimed my second spasm at her face and she took a direct hit in her right eye. Finally high enough to her face, my third eruption spewed out and into her recently opened mouth. Now towering over her open mouth, the remainder dripped from my glans landing on her outstretched tongue.

"Eat it, Mrs. O'Brien! Eat my cum! That's it swallow it all like a good cocksucker!"

She looked up at me through her one opened eye and emphasized that she was indeed swallowing my seed. I placed my still pulsating cockhead into her mouth and allowed her to suck the last few gobs. Exhausted we both collapsed in each other's arms onto the now unkempt bed.

As we slowly recovered, she was wracked with shame. "What have we done? I've never cheated on my husband? And you're just a boy! What have I done?"

Holding her in my arms I did my best to assure her that it wasn't the end of the world and that her husband need never find out. I certainly wasn't going to tell him. A few minutes later she was able to see my point.

"Okay but we must never do this again, " she tried to insist. Unfortunately my soldier had recovered and it was now pressing against her side as I stroked her boobs. Feeling it and then looking down at it as it started to salute, she exclaimed. "Oh hell. It would have been a losing battle anyway. " And with that she wrapped her hand around my instrument and started to play the tune again.

We spent the rest of the day and the next morning learning new ways to bring enjoyment and contentment to each other. I wanted to spend the night but both of us knew that my aunt would have had a fit. As I kissed her good-bye the next afternoon, her final words were "Thanks for fixing my screens, Dennis. "

I couldn't believe the coincidence but no sooner had she closed her door then who should pass me in the hall but, you guessed it, Maggie!

"Is that what they're calling it now, Dennis? Fixing screens?" Saying this snidely and without so much as a look back she hurried out the front door. This goddess had left me dumbstruck again. I started to go after her but ran into my aunt who was not pleased.

"You, young man, have some explaining to do. Meet me in my office!" When she used this tone, she was not to be denied.

My Aunt Bev was a fifty-year old dynamo. She was always on the move. My Mom said that she was amazed that without much help from my 'loser' Uncle Bob, she had almost single handedly raised the money to buy this small apartment building that she had renovated and turned into a rooming house. Somehow she found the time to do well in the fashion business as an advisor, further her education at night school and 'keep Uncle Bob in the fashion that he had become accustomed to. '

I, of course, saw her in a different light. Since coming to Toronto to work for her as her personal handyman, I fluctuated from outright fear to unbridled lust. Unfortunately, she worked such long hours that I never had a chance to act out my growing fantasies. In actual fact, I hardly ever saw her but so much had happened to me in the past few weeks that resulted in new feelings towards the women in my life. Ever since Mrs. Green had initiated me into the wonderful world of sex, I eyed every female, young or old, fat or skinny, short or tall, as potential sex partners. My aunt was no exception.

She was reasonably attractive for a woman of her advanced her age. She had short blonde hair and deep blue eyes that could turn to ice if you crossed her or angered her. I guess that was from years of living with Uncle Bob. Being in the fashion industry she dressed well and was always wearing styles that were up-to-date but more importantly showed off her top heavy figure to its best advantage. She was carrying a little excess baggage around her hips but when she walked in front of me, the urge to grab hold and pull her buns into my crotch was always there.

Following her into her office, I was jolted back to reality when she started to chastise me for being negligent in my duties as her rooming house handyman. She said that she had tried to contact me from her office on several occasions and I had failed to answer her messages. Stupidly I had become so caught up in the last few days with Mrs. Johnston and Mrs. O'Brien that I hadn't bothered to check the office answering machine.

Evidently the washing machine had broken down and the tenants in 2A had been unable to get hold of me to fix it but that was just the tip of the iceberg. They had complained that I was spending too much time in Mrs. Johnston's apartment and that I had been unavailable all day yesterday because I was in Mrs. O'Brien's room. Aunt Bev demanded to know why. What was I doing? I could tell that she was imagining the worst but hoping that I would have a reasonable explanation.

I tried to come up with the explanations about the stopped-up-sink and the screens but she wasn't going to buy that. Suddenly I had nothing to say. She knew she had been right.

"Dennis have you been sleeping with these two tenants? Have you been making them fuck you in return for doing these chores?" Her choice of the 'F' word startled me as she had never used such language in my presence before.

Sheepishly, I tried to defend myself by weakly responding, "I didn't make them, Aunt Bev. They wanted me just as much as I wanted them. I was so horny and.. and.. besides, Mrs. Johnston even paid me!" Oops. I think I had gone too far and given out too much information.

"What would your mother say, Dennis? She would be so disappointed in you. Why.. why.. you're just like your uncle! You even look like him. " Now, she looked like she had given out more information than she had intended. Recovering her composure, she followed with, "I have a good mind to send your promiscuous little body back home!"

"I'm sorry, Aunt Bev. Give me another chance? Please?" To this day, I still have no idea why I was begging to stay.

The silence was unbearable but finally she relented and said I could stay if I could control myself. Knowing that I was lying, I agreed.

The next couple of days were grueling. She had me trying to fix the washing machine, running all over town for parts. I had to paint the vacant room as a new tenant would be occupying it in two weeks. I had to wash the walls in the hallways and paint the bathroom in 2A's apartment. That was humiliating as the two tenants, who were obviously gay, made a point of watching me every minute, which of course, made me extremely self-conscious. To top it off, both Mrs. Johnston and Mrs. O'Brien tried to lure me into their dens, I mean their bedrooms. They were quite peeved at me when I resisted but I knew that my aunt was keeping a closer eye on me literally as well as figuratively.

Evidently, she had taken a bit of a break from her full time job as she seemed to be around much more. I really didn't mind although at times it seemed like she was undressing me with her eyes. I figured that it was just my imagination until the night I overheard her talking on the phone to my Mom.

"Yes, Janet. He's working out fine. Yes, he's turned into a fine looking young man. Yes, I can see that he is definitely a Mitchell. No, I haven't seen him dating any one. No.. no. Well, if you can keep it a secret. Now don't get angry but I found out that he had been sleeping with not one but two two of my tenants. Yes! Can you believe it? Your little boy, my little nephew is now a man! Oh don't cry silly! It's perfectly natural. Besides that, isn't it better that he learn about sex by fucking someone with experience rather than banging some young broad in the back of his Dad's car? Oh, don't lecture me about my language, Janet. Besides, if he wasn't my nephew, I might be tempted to seduce him too. Oh stop it! I'm just kidding. "

Yes, I know…yes…but…Janet…but…listen, you overprotective bitch, don't talk to me like that. It's not my job to protect your little cocksman from predatory females. I'm not his babysitter…. Besides that's easy for you to say. You've got a hard cock in your bed every night…. yeah, well, my Bob might not be much but at least when he's here, he knows how to satisfy a woman! Yeah, that's right. Since he's been in prison, I've been burying myself in my work. …. No there's no man there that interests me. They're all fags for Christ's sake. It's the goddamn fashion industry for Heaven's sake! All I've got to pleasure myself with is my vibrating dildo! …. What do you mean you're shocked? Grow up, it's 2001. "

denny9
denny9
656 Followers