I had recently been divorced, and had just turned 36 when I decided to make some changes in my life. I had worked myself up to superintendent of an N.Y.C. commercial real estate building and I decided to go for something less stressful. I wasn’t looking for less work, just something without the cutthroat aspect and everything needing to comply with an insane amount of regulatory paperwork.
After looking for a short time, I found what seemed the perfect solution. A residential complex in N.J. was looking for a maintenance super, and on top of that offered a free apartment as one of the benefits. I sent out my resume and after a follow up interview I had the job. Two weeks later I had moved into the complex and started work. The property manager had informed me that they had a tenant/ management meeting each month, which was the next evening, and I should attend so I could meet and greet the tenants.
The next evening at the meeting , after business was discussed, the property manager introduced me and I said a few words to the effect that I was there to help and that if they needed something done or just wanted to discuss an issue I was glad to listen.
The meeting had attracted around ten tenants and they started to file out the door. As I stood there, a short bleach blond woman with a teenager in tow approached me. “Mr. Schlage, my name is Ms. Duffy and this is my child Johnny.” “Pleased to meet you ma’am” I replied “how are you John? “ I said while extending my hand. He weakly gave me a handshake. “Well I’m glad there’s someone who looks like they’re not afraid to work here, after the last one they had” she said , attempting to smile. I explained I couldn’t comment on things before my tenure, but what was her problem. She said that her bathtub drain had been very slow draining for some time and previous complaints had gotten her nowhere. I asked if tomorrow morning was soon enough to look at the problem. She practically beamed at this and said though she had to work, her child was home due to a school break.
The next morning I arrived to assess the problem. Ms. Duffy was still there and she looked like she had tried hard to look nice. I saw the drain was very slow and I informed her it had to be snaked out, and I would return shortly. When I returned , she looked at the clock and said she had to leave. I went right to work and after only feeding a few feet into the drain, I encountered the problem. After some serious movement , the blockage cleared and I began retracting the snake. Attached to the barbed head of the snake was some type of pink fabric , with hair and soap scum adhered to it. As I disentangled the blockage from my snake, I heard a noise by the door. I turned to see Johnny standing there. He was around 5’5”, slim, very fair skinned with a few freckles by his nose. His hair was brown and longish, and his eyes were green. His features were pretty, as opposed to handsome and his lips were full for a boy. He was wearing a t-shirt and those lounge pants kids wear everywhere today.
The fabric I disentangled turned out to be a small pink thong. Holding it up, I kidded “Hey did your girlfriend lose this? “, although I was puzzled how it got there. His face turned bright red and he whispered something unintelligible before turning and leaving. Shaking my head, I packed up my gear and left the bathroom. As I passed through to the exit, I heard music playing softly. I went out and shut the door. I then cleaned and oiled the snake, before cleaning up myself. It was then that I noticed that my cell phone was missing, I must have dropped it while working. I returned to the apartment door and rang the bell. It took a few minutes and another ring before I heard a low voice “ Who is it? “ “It’s building maintenance, I was just here. I seem to have left my cell phone “ I replied. I stood out there for a couple of minutes, until I heard the door open. A girl stood there with my phone in her hand. She was dressed like a schoolgirl, with a short, plaid skirt, knee socks and a white blouse. She had on pink lipstick and had green eyes. “Thanks “ I said and took the phone. As I was turning to leave, a realization hit me. The girl had pushed the door, but hadn’t closed it shut. Holding my phone in one hand, I pushed the door open. The girl turned back towards me as I said “ Hey Johnny.”
When “she” turned I clicked the camera on my phone a couple of times, getting some candid shots. “What are you doing, oh my God “ she wailed. With a purpose in mind I quickly stepped inside and shut the door. “Calm down” I said “let’s discuss this.” I calmly walked to the couch and sat down. “What should I call you?” I asked “Johnny doesn’t seem to fit.” She whispered “Jenna”. “Ah Jenna, that’s a pretty name. Sit down and talk to me” I said. “I don’t have to” she said, but she sat down. “How long have you been dressing up?” I asked. “Around 5 or 6 years” she answered in her whisper voice. “Do you want to be a girl?’’ I asked. She just nodded yes. “And does your mother know about this ?” I said while staring into her green eyes. I saw fear in her eyes and she mumbled “No”. ‘What about your friends at school.” She just shook her head no. I stood up and moved in front of her . I reached down, cupped her chin and tilted her head towards me. “You don’t want these pictures to be seen, right Jenna.”
“No I don’t. What do you want?” she answered. I smiled while maintaining eye contact. I put my hands in my pockets and adjusted my pants back, so that my growing bulge showed clearly. I took one of her hands and placed it over my hardening cock. She recoiled and said “No I can’t”. “Your choice, it would be such a shame if those pics ended up on the internet or something.” I saw defeat in her eyes. “Ok, what should I do?”
“Start by freeing my cock” I said hoarsely. She slowly reached out and unbuckled my belt, then unbuttoned my pants. With both hands she reached up, gripped my pants and then pulled down taking my under shorts as well. My cock sprang free, and she made a little gasp. It felt as hard as iron. It was just over six inches in length and somewhat wedge shaped. At the base I was thickest, around as thick as a can of red bull. It tapered as it approached the head, with the head larger then the shaft beneath it. Jenna tentatively reached out a hand and touched it sending a thrill through my body. “That feels nice, now put it in your mouth” I said.
Jenna opened her mouth and cautiously took the head inside. I placed a hand on her head and slowly pushed her head down, forcing more into her mouth, until my head reached the entrance to her throat. “Just go that deep for now, so you don’t gag” I said “now move your head up and down.” Jenna did as I said and started to bob her head , giving me extreme pleasure. “Now put your hand on the base and take it as deep as you can” I instructed. Jenna had a small hand and she didn’t come close to fully encircling my girth. She began to take me as far as she could in her mouth, building up a good rhythm, when I pushed hard on her head while also thrusting my hips forward. I forced my cock into her throat causing her to gag. I withdrew myself, also releasing a good amount of saliva from Jenna onto my cock.
“Put your hands on the back of your head “ I ordered. When she did I placed my left hand on top of her hands and guided my erection back into her hot, wet mouth. “Look up at me Jenna , I want to see your pretty face and green eyes while I fuck your mouth.” Jenna looked up and met my gaze. I began to pump her mouth, trying not to gag her. For the most part I succeeded, but a couple of times I went too deep, gagging her and tearing up her eyes. I knew I couldn’t last too long so I started to increase my pace while only putting my head and the top of the shaft into her. “Use your tongue, swirl it around me” I said and Jenna complied pushing me to the edge. I thrust a few more times and felt the flood begin to release. It had been a while since I came and my balls were full. I let the first two blasts shoot deep into her mouth, then I pulled out and began to paint her face. One blast went up her nose, another grazed an eye, a few shots landed in her hair with a good amount all over her face. “Open your mouth” I said as I squeezed the last few drops onto her little, pink tongue.
“Now clean off my cock with your tongue and do a good job.” Jenna held my cock in her soft hand and stared at it, almost transfixed for a moment. She then began to alternately lick and kiss my cock , all the time gazing lovingly at it. After a couple of minutes of this Jenna stopped, looked up at me and said
“I’m finished. All done.” I looked down at her and I noticed her left hand was under her skirt making little circular motions. I reached down and guided Jenna up. As soon as she was standing , I grabbed her hair,
leaned down and kissed her. I was dying of thirst and her lips were water and I drank my fill. When I broke the kiss Jenna seemed to lose her balance, though I steadied her. “Mmm, you made me weak in the knees” she whispered in her breathy voice. “Jenna” I said “let’s go to your room.”
Jenna looked at me with a shy smile, took my hand, said “Ok” and led me to her room. It was a nice sized room, painted a shade of off-white (the complex only allowed white and off-white options for paint as part of the lease agreement ) with a white dresser and a white nightstand. She had a double bed with a brass headboard and a small desk with a backless bench seat. I sat on the seat and pulled Jenna onto my lap.
I started to kiss Jenna again. With her so close I could smell her hair, all clean with a touch of citrus, as well as a hint of something floral, perhaps body wash or a trace of perfume. Jenna parted her lips as I kissed her, and I slipped my tongue into her mouth. Jenna’s tongue eagerly met mine, and our tongues circled and swirled. While kissing, I caressed her back through her blouse with one hand while my other was rubbing her leg, just above the knee. As my fingers crept up to mid thigh, Jenna broke the kiss and let out a low moan. While my hand kept roaming, I took the opportunity to begin kissing and nibbling her slender, white neck. Jenna really liked that and started squirming while whispering in my ear “Don’t stop, that feels so good.” All her squirming was really stimulating my cock, which had never lost its erection, which for my age was amazing. I could always get it up again, but keeping it hard like this was unusual. I moved the hand from Jenna’s back and slid it under her blouse, burrowing under her padded bra. My fingers found Jenna’s nipple and I tweaked it, bringing another moan from her.
Shifting her weight on my lap, I stood up, carrying her, took a few steps and placed her on the bed. I now removed my shirt and pants, which had been at my knees, as well as my socks and work boots and knelt on the bed. I removed Jenna’s shoes and socks and began to kiss Jenna’s feet . They were small and smooth and the toenails were painted pink. I began to work my way up one thigh, kissing and feeling as I went. It was unbelievable how smooth and creamy the skin of her legs was. I thought my ex could have taken lessons. I worked my way to the top of one leg and I just brushed my lips over her pink panty covered bulge before starting to make my way down her other leg until I reached her foot. Taking her feet in my hands, I kissed each toe. “Your toes are so cute” I said between kisses. “Yeah, that’s the one place I keep all girly, cause no one sees” Jenna answered. “You look pretty girly everywhere “ I replied which made her smile.
I now pushed up her short skirt to her waist, revealing her pink panties, with a slight bulge. My hands gripped one side of the panties and I ripped through between the waist band and the leg hole. I repeated this on the other side, pulled the torn panties off Jenna and threw them off the bed. Jenna was almost hairless down there, she had just left a small triangle of downy smooth hair. She had a small penis, with tiny balls which were smooth. Jenna’s penis was very thin, and looked to be around three and a half to four inches long. I bent down and gave her “clit” a quick kiss, then I grabbed both her legs and lifted them up and towards her chest revealing her little pink asshole. While holding her legs up I began to eagerly tongue her hole, to which Jenna grabbed my head with her hand and pushed me closer. “Does Jenna like when I lick her little hole?” I asked. “Oh yes, it feels good, don’t stop” she answered. I shifted both her legs to one hand, so that my other hand could spread her cheeks and I could force my tongue more to her hole. It was very tight so I drooled all over her ass and then I began to push my index finger into her. After some initial resistance I worked my finger in, and was rewarded with Jenna’s moan of “Oh yes” as well as her tight little hole clamping down on my finger like a vise.
I slowly worked my finger deeper until it was all the way in. I then withdrew most of it before pushing it back in. I then began to slowly finger fuck Jenna’s ass to her obvious enjoyment. She had her eyes closed and was making little sounds as I did. After a couple of minutes of this, I started to wiggle my finger, trying to stimulate her prostate. When I found it, she let out a loud groan. I then took my finger out and while spreading her ass, I spit a couple of times onto her winking hole. I told her to take hold of her legs, and after she did, I then inserted two finger in her which was a tight fit. I worked them slowly in her and then bending down I also began to lick the top of her clit, just below the head. I made little circular motions with my tongue, stimulating the sensitive skin. I also made sure my fingers were hitting Jenna’s prostate with each thrust. She was becoming more and more excited. She was moaning louder and her pale face was becoming flushed. At this point I squeezed a third finger into her, which pushed Jenna over the edge. As I forced the third finger deep, I increased the speed of my tongue to a blur. Jenna grabbed my hair and wailed “Yes, oh yes, I’m coming”.
Jenna’s tight young body stiffened, my fingers were clamped so tight I couldn’t move them and Jenna began to spurt come. I watched as she shot 5 or 6 spurts onto her skirt and skin. Her body then began to relax. Keeping my fingers in her, I took her clit in my other hand and stroking it coaxed the last bit of come from her. I then stretched up so I could kiss her pink lips. “Did Jenna like that?” I teased “did she enjoy her orgasm?” “Oh yes daddy “ she told me “it was the best I’ve had.”
“Jenna” I said “I need you so bad. I want to be in you, I need to fuck your tight, pink asshole before I explode.” Jenna looked at me with her green eyes and answered “ I want you to fuck me, but I’m a virgin. So be careful because it’s so thick.” I kissed her lips again while continuing to twist my three fingers in her to prepare her hole. I then took them out and had Jenna get on her hands and knees with her cute round ass over the edge of the bed, sticking up in the air. I spread her cheeks and began applying more spit to her hole. Due to the finger work I had done, her hole was now slightly open. I then coated my cock with more saliva and placed it at her quivering entrance. “It’s best to relax” I said “and it might hurt some, but I’ll take it easy.”
Spreading her cheeks as wide as I could, I popped my head inside. Jenna gasped as I broke the ring, so I waited a minute before inching forward. When I was halfway in her I stopped. “Jenna” I said “now I want you to start moving. Go nice and slow to start and you don’t have to rush taking it too deep. If I start ,I don’t think I can control myself now, you have me so hot.” Jenna slowly started to move, pulling her ass forward until just my head was in her, then back swallowing more of my cock. With each thrust Jenna took a little more into her, until there was just an inch to go. “Daddy help me” Jenna said “it’s so wide, just finish it for me.” I grabbed her hips and thrust forward, burying my cock all the way until my balls slapped her hot ass . Smacking her ass I told her to start moving her caboose again. Jenna laughed , but she began to start fucking me again. I watched as her ass swallowed then released my cock. Jenna had a very small waist and hips that flared out a decent amount. Her ass was round with a nice shape. It could use some more padding, but I knew some exercises that could help with that. As I watched her engulfing me, I noticed she had brought one of her hands between her legs and she was rubbing herself.
This turned me on even more and I had an idea. I pulled out of her hole, at which Jenna made a disappointed sound. I sat on the bed with my feet on the floor. I had Jenna straddle me, and I guided my cock back into her paradise. I then had her put her arms around my neck and I grabbed a hold of her thighs just below her ass. I then stood up, which caused her hole to slide all the way down my cock. Jenna weighed around 120 lbs. which I could easily support. Jenna’s closet door had a long mirror on it, so I stood in front of it , but turned sideways. This way we could watch in the mirror, while Jenna bounced up and down my pole. We did this for a while and I could feel Jenna’s hard clit against my stomach. Watching in the mirror like this was driving me even crazier than just the fucking and I wasn’t sure how long I could last.
I carried her back to the bed, and managed to grab and position a pillow near the edge. Then while somehow staying deep in Jenna, I managed to fall on top of her on the bed with the pillow under her ass. I kept one foot on the floor, while resting on my other knee. I leaned forward so my face was inches from Jenna’s and with our bodies touching, I began grinding into her. Then supporting myself with my elbows, I grasped both Jenna’s shoulders to keep her from sliding. I then began thrusting all the way into her tight love channel. Jenna was really getting into this. She was moaning like crazy and between moans was talking dirty. “Oh yes, fuck your girl, don’t stop. Give it to me hard, come on daddy, give it to your girl.” Her talk drove me to increase my efforts, driving my cock as hard and deep as I could, my breathing becoming rapid. “Yes, yes , don’t stop daddy” Jenna cried and she then bit my shoulder and shuddered. The pain of her bite I barely felt, as Jenna’s body began to spasm beneath me. My cock felt a viselike grip on it, and I felt Jenna’s clit releasing itself between our bodies. This was too much for me to take and I cried out as I started t come violently in Jenna. This orgasm was more intense then anything I could remember and I felt like I might pass out from it. We stayed like that for a few minutes, though finally Jenna opened her eyes. “Wow, daddy that was awesome “ she whispered. “Oh my God, that was the best sex I ever had. My ex could take lessons from you, little girl” I said “but why call me daddy?”
Jenna smiled from the compliment and answered “All the girls in my school call their boyfriends daddy. Was I really your best or are you kidding.” “No, I’m not kidding Jenna” I said, then I kissed her before I slowly pulled my shrinking cock out of Jenna’s ass. I then rolled onto my back and lay there. Jenna got to her knees and leaning over me, began to graze my body with her hair, starting at my chest and working her way down until reaching my feet. She then worked her way back to my cock. After tickling my cock with her hair, she took it in her hand then began to lick it. “Tastes good” she said “because I keep my ass clean. I’ve always known I wanted to do this stuff. But I didn’t think I would be so lucky to do it with someone as good and handsome as you.” Jenna smiled and then began to lick me again. It was all too much for me. With my balls drained, I fell asleep like that.
When I woke up an hour later, Jenna was sitting on the bed looking at me. She was fully dressed and her make up was retouched. “Why did you let me sleep?” I said. Jenna smiled and replied “Daddy looked so peaceful and handsome, plus you worked so hard making me come.” I sat up and kissed her. “Are you my girl Jenna, do you want that? I’m pretty old for you.” I saw something cross her face. ”You don’t want me ?” she asked like she might cry. “Oh God, I want you Jenna, I’ve never wanted anyone more.” She smiled shyly again and said “Good because I want you. It’s just you’re so handsome, I’m worried a little. Did you know my mother thinks you’re hot, even though she has a boyfriend, but he’s a jerk..” “Well Jenna, it is you I want so don’t worry” I sad emphatically . She smiled again and said “What are you doing tonight?” “I don’t have any plans” I truthfully answered. Jenna jumped up and grabbed a bag from her dresser. “Can you bring this to your apartment? It has some make up and clothes in it . This way I can visit you, if you want, and I can make myself look good for you.” I smiled at Jenna and said “That’s a great idea Jenna and you are always welcome.”
“Cool” she said “but I’ll be careful. I don’t want the complex talking about the super screwing some sixteen year old freak.” “Well, being careful might be smart so you don’t upset your mother. I take it she’s not understanding.” “No she’s not, one time I tried to mention something about how I felt, and she was so nasty and wouldn’t let me get a word out. I don’t bother anymore.” I reached out and caressed her face. “Maybe some day she’ll come around. It’s possible” I said. “Maybe” Jenna answered “but I don’t have school tomorrow. Can I come by tonight-and you could fuck me again?” “Yes” I said smiling “by the way Jenna, here’s my phone if you want to delete those photos. I was just bluffing, I just wanted to get in you panties.” Jenna smiled and said “Keep them if you want. Maybe you can take more tonight when we fuck.” I just grinned in reply.