When I was a high school senior I was a skinny, shy kid. Although I didn’t have a problem talking and communicating with my guy friends, I clammed up when talking to the girls. As you can guess, it was frustrating when my friends started hitting on and dating the girls. I felt like a fish out of water.
In my high school years, my body changed big time. I have always loved football and decided to play in high school. My commitment to play brought me to the gym for conditioning. I lifted weights four to five days a week, minimum. Within months, there were noticeable changes to my body. I went from skinny skin and bones to a solid muscular frame. My image and confidence in my body changed as well. However, no matter how much my body changed, the shyness I had when it came to talking to girls never changed. It was so frustrating for me.
It’s not that I didn’t want to talk to them; I just never felt they would like to speak to me, let alone date me. So, I had to settle for fantasizing about them as I jerked off. I have to confess, though, that most of my fantasies were not about my classmates. Most were limited to Mrs. Demarco, whom I called Mrs. D.
Mrs. D was the sexiest woman on earth, in my eyes. She was in her thirties, with long blonde hair, blue eyes, beautiful long legs, big tits, and a fantastic ass. She was a widow. Her husband was tragically killed in a car accident about two years ago.
I can’t even guess how often I sat in my bedroom looking out and watching her head off to work. She was always a fashionable dresser and looked sexy going to work. I used to think how she must have had all her male colleagues daydream about her all day; I know I would have. But it was when she went out at night that would blow my mind and my load. She always looked so sexy, not the conservative dress that she wore when off to work. The kind of dress you would see women wear at the club. Short, tight dresses or skirts, revealing tops. Her tits were usually ready to pop out of the tops. I would dream about meeting her at the club. We danced, drank, and had a good time. Which, of course, led us to go back to her place as we fucked the rest of the night. My dream had to move quickly because it never took long before I was shooting my load.
The spring brought some warmer-than-usual weather. My father decided to open our pool early because of that weather, and once it was up and running, he and my mom decided to have a weekend BBQ. That was one thing about our neighborhood: everyone had a pool, and because they worked long hours during the week, they loved their pool parties.
This pool party was like most of them—there was a lot of beer, liquor, soda, and food. The guys all met at the bar to discuss business and sports. I don’t mind that part because they always like my opinion on how the team will be and who looks promising since I am now the team captain.
The conversation turned quickly when Mrs. D arrived. All the men stopped talking and just watched as she walked across the patio to where the other women were. She had on a black bikini and a pair of black heels. There wasn’t much of a surprise since Mrs. D always wore heels. The quiet was broken when Mr. James just mumbled out, “Just one time, I would die a happy man if I fucked her just one time.” All the others agreed with his statement with their head nods. The topic of discussion quickly went back to talking about their stocks when they realized I was still with them.
I knew I was not supposed to be with the men then. I went to the other side of the pool and camped myself out on a lounge chair. I didn’t mind, though, because I could lounge on the chair, wearing my sunglasses, and no one could see that I was spending the day looking at Mrs. D.
I could see Mrs. D. was talking with my mom. They kept looking over at me. I couldn’t imagine what that was all about. Once they finished, Mrs. D started walking over to me. I was nervous; oh my god, did she catch me staring at her? Is that what she was telling my mom? The nervousness went away as I watched her approach me. Her tits bounced with every step. I was hearing the click of her heels on the concrete patio. Oh no, I could feel my dick starting to grow.
She approached me and sat on the lounge chair next to me. My eyes locked on those tits that were barely covered by her bikini.
“Hi Cory, I have something to talk to you about.”
Feeling the anxiety come over my body. “What is it, Mrs. D?”
“Well, Cory, I was talking with your mom, and she said it was okay to ask you this. The weather is getting nicer, and taking care of my property is getting too much for me, so I am looking to hire someone to take care of it. Would you be interested in doing that?
“I will pay you $15.00 per hour, and you can set your hours. I don’t want things to get away from me and out of control. Your mom told me you are conscientious and take care of your lawn. It always looks nice so that you would do a good job.”
I was taken aback by her offer—something I never expected.
“Please let me know as soon as possible because my grass is already relatively high. If you don’t want it, please give me the name of another boy you think might like it.”
My mind was racing as I thought to myself. Oh my god, of course, I want it. I can be closer to you. I see you a lot more and get paid for it. I blurted out quickly, “Thank you for the offer, Mrs. D; I am honored you thought of me. I don’t have to think about it. I will be happy to do it.”
She smiled and thanked me. “That is one less thing I will have to worry about. My lawn mower is in the garage, and gas is in the can next to it.”
I told her that, since it was already high, I would be over tomorrow to cut it for you. She was thrilled and thanked me before getting up to walk back to the other women. I watched as her tight ass wiggled as she returned.
I looked around but didn’t notice anyone looking, so I got off the chair and went to my room. I was thinking back about how I saw her tits poking out of her bikini and how her ass wiggled as she walked away. You can guess it. I was hard quickly and stroked my cock once again, thinking of Mrs. D. After cleaning myself up, I returned to the party; no one even knew I was gone.
The next day was Sunday; about 11:00 AM, I went to Mrs. D’s. I knocked on the door to tell her I was there so she could let me into her garage. The door opened, and there stood Mrs. D. She was wearing a pair of tight blue shorts and a crop top. It was apparent she didn’t have a bra on since her nipples could be seen through the light material.
My mouth must have dropped open, and I stuttered as I said, “Good morning, Mrs. D. I’m here to cut your lawn.”
She was thrilled that I was there. She took me to the garage and showed me how I could get in if she weren’t around and where all the equipment I needed was. I got busy cutting and trimming her lawn. It was a hot day, so I took my shirt off, hoping to get some sun as I worked. The whole time, I thought about how she looked in that outfit and how sexy she was.
As I put everything away, Mrs. D opened the garage door and asked me to come in for a little while. I put on my shirt and went inside. Mrs. D was in the kitchen. She had a cold drink on the table. “Here, Cory, you must stay hydrated in this heat, sit and cool down, and drink.” Well, she didn’t have to twist my arm since it gave me more time to see that sexy body of hers.
Besides Mrs. D being a beautiful woman, she was also very cool. As I sat there with my drink, she started asking about me. We talked about how I liked playing football, my plans after I graduate next year, and how I am doing in school. I sat there for about an hour talking with her before leaving and heading home. And, of course, I couldn’t wait to get up in my room. Yes, once again, there were hundreds of little sperms that sacrificed their lives when I blew a massive load into a tissue. I hope they realize they died for a good cause.
Mrs. D gave me a list of things she would like to have done. I would go and complete the task whenever I had time. I wanted to go and do them when she was home because she wore some skimpy clothes, and I loved that. Some days, I felt like I hit the lottery when she was by her pool in her bikini.
It was late on a Friday, so I went to Mrs. D to cut her lawn. I didn’t bother her since I now knew where everything I needed was. It was hot, so I took my shirt off and started mowing. I cut the front and went to the back. I looked over, and Mrs. D was sitting at her patio table. I looked over, and she waved at me, so I waved back and finished my job. Once I was done, I walked back to the pool area and apologized to her. “For what,” she asked.
“I didn’t think I would interrupt your relaxing time.”
“Oh, don’t be silly, Cory. You didn’t interrupt anything.”
She had a picture of cold water on the table and poured a glass. “Please sit, Cory, and join me for a while.”
I was looking forward to our little chat sessions after I was done. I sat on the chair across from her. I had not put my shirt back on since it was a hot night. Mrs. D was wearing a floral sundress with a low-plunging neckline. It’s always a plus to enjoy our conversation and get to see her sexy body as well.
We discussed our week, and Mrs. D asked me why I mowed her lawn tonight. “Don’t you have a date?”
I looked away and was embarrassed when I mumbled, “No, I don’t.”
“You mean you don’t have a girlfriend,” she asked.
“What is wrong with the girls in that school? I would have thought you would fight the girls off with your good looks and solid body.” The first thought that ran through my head was she thinks I have a sexy body.
I went on to tell her that I was timid and not very good at talking to girls. Mrs. D sat forward in her chair and took hold of my hand to comfort me. When she did, I was able to look right down her dress. Her tits were in full view. I felt my cock starting to react. Then panic set in as I didn’t want Mrs. D to notice. I squirmed and moved, hoping she didn’t notice. She was talking, and to be honest, I had no idea what she was saying since I was so focused on trying to hide my hard-on. I couldn’t take it anymore. I blurted out, “Mrs. D, I must go home.” I jumped up, trying to hide my hard-on as I did, but I don’t think I was successful. I walked to the gate, but before I left, I turned back to look at Mrs. D. She smiled at me and waved goodbye. I waved back and ran home.
When I got home, I needed to take care of the essential things first. So, after I jerked off, I lay there on the bed thinking. There is no way she didn’t see my hard cock poking into my shorts. I didn’t know what to do, but I also knew there was nothing I could do. If she saw it and wanted to fire me because of it, there was nothing I could do. I just didn’t know how I would tell my parents that I was fired because I am a horny degenerate, and my cock got hard when talking to Mrs. D.
Over the next week, I went to Mrs. D to complete some tasks, but she was at work when I was there. It wasn’t until the following weekend that I went to mow the lawn again. I got the lawn mower out and mowed and trimmed. It was my first time working since I ran home because of my hard cock. Mrs. D never came out or was in her yard doing something. I remember thinking to myself, I knew she saw me. That is why she is not out here. She is hiding; she knows how much of a pervert I am.
I was near finishing when the sky darkened, the wind kicked up, and it started thundering and lightning. I watched Mrs. D leave the house and head to the patio. She frantically gathered the cushions off her lawn furniture before they blew all over the neighborhood. I put the lawn mower away and ran over to help her. The skies opened up in seconds, and it started to pour.
We were drenched by the time we got the cushions into the garage. Mrs. D thanked me for the help. When I turned to look at her, my eyes almost popped out of my head. Her tank top was soaked, and her nipples were visible since she didn’t have a bra on.
She reached out and held my hand. “Come inside, Cory, and dry off before you catch a cold.”
I followed her like a lost puppy dog. I could feel my cock already rising to attention. She grabbed two towels and moved over to me, “You better take your shirt off, Cory, so you can dry off and warm up.”
Mrs. D took hold of the bottom of my shirt and raised it over my head. She then grabbed a towel and started toweling me off. As she stood in front of me, drying me off, her tank top still soaked and her nipple poking out, I could feel my dick getting even harder. “Oh god,” I thought. There is no way she isn’t going to notice my dick sticking straight out. I started to feel panic come over me.
Then she stepped back a step or two, and without notice, she removed her tank top. She stood in front of me topless with her huge tits wet and glistening right in front of me. “I’m chilled to the bone; you don’t mind, do you, Cory?”
I looked down and away, feeling embarrassed. “UM, no, I don’t mind, Mrs. D.”
It’s not much different than being in a bikini top, and I see you always looking when I am in one of them. I felt myself get even more flustered. Before I could even deny it, she gently touched my face and told me it was okay. She liked it when others checked her out. It was a compliment that they think I am pretty.
“You do think I’m pretty, don’t you, Cory?”
Still looking away and down, I just mumble, “Yes, Mrs. D, I do.”
She stepped closer, put her fingers under my chin, and pulled my head up to look at her. Cory, “I am a little worried about you. I want to help you overcome your shyness and feel more comfortable. I want to show you the enjoyment you can have if you come out of your shell. Wouldn’t you want to enjoy everything, Cory?”
With Mrs. D still holding my chin, my eyes looked into the sexiest brown eyes I have ever seen, and I whispered, “Yes, Mrs. D, yes, I would want that more than anything.”
You promised me you would never tell anyone, right, Cory? I tried to look away, but her fingers were still under my chin. She wouldn’t let me. “I promise, Mrs. D.”
She went on to tell me that she was so much in love with her husband, and it crushed her when he died. She doesn’t want another man and doesn’t want to date anyone, but she went on to say how she hates her bed being so lonely. She explained that she still has sexual needs, and she thought that I could help her with those needs, and in return, she could help me be more comfortable with others.
I couldn’t believe what she was saying. She said, “I see you watching me, Cory; you have naughty thoughts about me, don’t you? I tried to look away.
“No, Cory, look me in the eyes and share that with me.”
It took me a while, but with her encouragement, I went on to tell her how I would sit in my bedroom, watch her leave, and think about making love to her. I was embarrassed, and she saw that I was. She told me not to be and told me I was no different from anyone else. She asked me if I ever noticed the men in the neighborhood and how they looked at me. “They have those same thoughts, Cory.”
That made me think of Mr. James’s comment at the BBQ. I thought she was right, and I was no different than them. She saw a smile come over my face. She put her hands on the side of my face. “I like that smile, Cory; I want to see that smile more often.”
She then leaned in and kissed me. It was a soft, sensual kiss at first, but then she opened her mouth and worked her tongue into my mouth. Now, although I haven’t ever kissed a girl, I did know the concept and worked my tongue into her mouth. Our kiss became more intense and passionate. As we continued to kiss, Mrs. D took my hand and guided it to her bare breast. I understood what she wanted and started caressing and squeezing them. I figured I must have been doing something right because she began moaning into my mouth as we continued our kiss.
She broke our kiss. She told me that was nice, her lips inches from my mouth. I want to make you feel good now, Cory. Is that okay with you? I was at a loss at what she would do, but at this point, I didn’t care. My voice shaking, I mumbled out. “Yes, it’s okay.”
As she stared into my eyes, I felt her hand slide up my leg and into the leg of my shorts. It felt so good to have someone caress me like that. Then her hand took hold of by now my rock-hard cock and stroked it with her fingertips. As she was doing that, I watched as she moved her tongue back and forth slowly over her upper lips. I had no idea what the meaning was, but I did know it was so fucking hot to watch.
I started moaning. Mrs. D moved closer and whispered, “Doesn’t that feel good, Cory?”
I couldn’t answer; I just nodded my head yes. Mrs. D then pulled my shorts over my hips. I raised my hips off the stool, and she lowered them all the way and took them off me. She stood there smiling. “Oh, Cory, you have a beautiful cock. It is much better than I imagined.” She looked at me with a smirk on her face, “I’m going to show you the pleasure a woman can give you with her mouth, Cory; you wouldn’t mind that would you?”
I mumbled out, oh no, I wouldn’t mind. Watching enough porn in my young life, I knew what she meant. I watched her bend over and wrap her lips around my cock, and swallow me to the base. I loudly moaned, “Oh god, that feels so good.”
My cock slid between her lips as she took me in and out of her mouth. I have watched blow jobs in porn movies, but God, I never knew they felt this good. I couldn’t believe this was happening to me. I was moaning louder, and my body was tingling as I started to breathe heavier. My legs started shaking, and before I realized what was going to happen, I felt Mrs. D’s lips wrap tighter around my cock. My body tensed; I tried to warn her I was going to cum, but it was too late. My cock pulsated in her mouth as I shot stream after stream of hot cum into her mouth. She continued to suck it all out of me and swallowed every drop I could give her.
As my dick went limp, she took her mouth off my cock. Still reeling from it all, I couldn’t talk. Mrs. D stood up and kissed me on the cheek. “Did you like that, baby?”
“Oh fuck, that was amazing. I never felt anything that good.”
She smiled at me and told me that was just the beginning. She grabbed my hand and walked me upstairs to her bedroom. She sat me on the big, king-sized bed and stood in front of me as she undid her shorts and lowered them. Standing there in front of me naked, I couldn’t take my eyes off her bare smooth pussy. It was fucking awesome. She pushed me back onto the bed and crawled next to me.
Hovering over me, looking into my eyes. “What do you want next.”
I couldn’t think straight and only could answer, “Oh, I don’t know, anything you want.”
“Oh no, that’s not how this works…you want something else, tell me what you want. You need to speak up and tell people what you want. If you don’t, you won’t get anything.”
I felt fear move over me as I thought oh fuck, I don’t want that. So, I mustered up the courage as I told her.
“I want to please you. I want to make you cum.”
She smiled at me and rolled off to the side. Yes, baby, I like that idea. She put her feet on the bed, raised her knees, and spread her legs for me. Yes, baby, I do like that thought. Come and lick me. I moved down between her legs. I couldn’t believe I was there looking into her pussy. It glistened because it was so wet. She reached down and spread her lips for me, lick it, she whispered. I moved n and licked her slowly up her slit. She moaned loudly as I did and encouraged me to keep licking her like that.
The faster I licked her, the more she squirmed and moaned, so I just used my tongue to lick as fast as I could. She pointed to a little nub down there and told me to lick her there. I did, and I knew I was doing something right by her reaction. Her hips raised as she ground them into my face. Her hands went to the back of my head and pressed me into her. She continued to beg me to keep licking her. Then, with one hard thrust up into my mouth, I felt her body shaking. She yelled out, “Don’t stop. Oh yes, I’m cumming!”
Her hips continued to push up into me as her body squirmed on the bed until her body went limp, and she lay there limply and breathing heavily.
I crawled up on top of her. We kissed as we held each other tightly. Mrs. D continued to squirm and breathe heavily. She ground up into me. That is when I noticed I was hard again. She felt it and wanted it as she ground more into it. She whispered in my ear, “Cory, fuck me, I want to feel you deep in me, put your cock in me and fuck me.”
It didn’t take much coaxing. I wanted to be in her and wanted it now. I moved between her legs and guided my cock to her pussy. I remember thinking this is it, my first fuck, and I am losing my virginity to the most beautiful woman in the world. With that, I pressed my hips into her. My cock slid slowly into her. I remember thinking it was the best feeling in the world, feeling my rock-hard cock slide into her hot wet pussy.
Mrs. D begged and screamed, pleading with me to fuck her faster and harder. Wanting to please her, I pounded my hips in and out of her. I knew it wouldn’t be much longer for me because I could feel my cum boiling deep inside me. I thrust hard and deep into her, feeling her legs wrap around my hips as she held me tight. I couldn’t hold back anymore. I was ready to explode. I let out a scream, thrust as hard as I could in her, and kept it there as I pumped deep into her. As I was cumming, I felt her hands grab tight around me and felt her body shake as she came in a hard, wild orgasm. I collapsed on top of her. Both lay quietly for what seemed like forever.
That was the first of many days I spent in Mrs. D’s bed, learning and welcoming her guidance. She did bring me out of my shell, and although I didn’t want to be without her, she pushed me into dating someone my age.
I started dating Joanne Henderson. Joanne was a beautiful girl with long, black hair and brown eyes; she was petite and had small, perky tits.
At the start of our relationship, Joanne didn’t want anything to do with being sexual. I didn’t push that because I always stopped by Mrs. D’s after my dates to tell her all about them. She never disappointed me, ensuring I had a good release before going home.
As our relationship grew, Joanne became more interested in sexual adventures. It started slow, first allowing me to caress her tits and then eventually letting me finger-fuck her. She felt guilty that she was getting all the releases, so one night, she jerked me off. It felt good, but I went straight to Mrs. D’s, like every other date I went on. She loved hearing about my first experiences with Joanne, but never failed to give me a better release. Things kept progressing with Joanne, hell, one night, she even put her mouth on my dick, but I still couldn’t wait to get to Mrs. D.
Then, one weekend, my parents were planning one of their BBQ pool parties. They asked me to invite Joanne. I put it off, telling them she might be busy. I didn’t know if I wanted her and Mrs. D together; I wasn’t going to do anything to jeopardize what I had.
Two nights later, while lying next to Mrs. D after one of our fantastic fuck sessions, she asked me about the BBQ and asked if I was going to be there. I told her I was, and my mom wanted me to invite Joanne. Mrs. D quickly jumped in, telling me that would be a great idea; why don’t you? I have heard so much about her and would love to meet her.
I was nervous, but I decided to invite Joanne. I went and picked her up early, so I was back to help my mom set up for the BBQ. Joanne wore a floral one-piece; she looked hot in it. As the adults arrived, Joanne and I stayed out of the way, sitting on the lounge chairs across from the bar where all the adults congregated. I introduced Joanne to everyone as we met them.
Mrs. D, in her typical fashion, made her grand entrance a little late. She walked in in a yellow bikini and looked gorgeous in it. As usual, as she walked in, the men leered at her, and she knew it as she swayed those hips for them to see. I chuckled to myself as I thought all these men were fantasizing about Mrs. D what would they say if they knew I was fucking her constantly.
I was brought back to reality when Joanne asked me, “Who’s that?”
I told her that it was Mrs. D, our neighbor, and then told her the whole story about how tragically she lost her husband. Joanne told me how sad that was and how sorry she was to hear that, but then told me how gorgeous she looked.
I saw Mrs. D watching us from a distance, but I must admit my anxiety built when she started to make her way over to us. Once again, I watched as she walked towards us, her tits bouncing and her heels clicking on the patio. As she reached us, Mrs. D walked over and sat beside me. “Hello, how is everyone doing on this side of the pool? Hi Cory, it’s been a while since I saw you. How are things?”
“I have been well, Mrs. D. I’ve been busy but good. Thanks for asking. This is Joanne, Joanne, this is Mrs. D”
She extended her hand to Joanne as they shook. “Are you two dating? You hit the jackpot, Cory; she is beautiful.”
Joanne thanked her for the compliment, and they sat and talked for about an hour before Mrs. D returned to the adults. But as she was leaving, she looked back at me, winked, and told me not to be a stranger with a big smile on her face. I assured her I would not be.
Joanne told me she liked Mrs. D and thought she was very nice. We sat there talking until Joanne asked me where the bathroom was. I told her I would show her. I walked her to the upstairs bathroom and waited in the hallway for her.
When Joanne came out of the bathroom, she approached me and kissed me—a hot, passionate kiss. After the kiss, Joanne looked at me with a smile and asked is this your room? I told her it was, and she asked if I would show it to her. I opened the door and took her in. She was pretty giddy and acting a little different than usual. She approached me and kissed me again, but this time, as we kissed, her hands found their way to my crotch. It wasn’t long before my cock was rock hard.
Joanne put her hands in my swimsuit and pulled it out. She stroked it as it continued to grow. I was surprised when Joanne dropped to her knees and took my cock in her mouth. This time, it wasn’t once or twice up and down with her mouth. She spent time at it, and she was doing a great job.
I was confused because Joanne never really showed interest in it, but then she shocked me even more when she stood up, pulled her suit off, and told me she wanted me to be her first. Mrs. D taught me well; I didn’t waste any time. I laid her on the bed and was soon between her legs, licking her. She loved that for sure, as it didn’t take long before she was coming all over my face.
I was hoping she wasn’t going to change her mind now that she orgasmed, so I moved between her legs and quickly placed my cock against her slit. I then felt guilty as I thought I might be rushing her. With my cock still resting on her pussy I looked down at her and whispered, “Are you sure?”
Joanne just looked up at me and shook her head yes. I push my hips into her ever so slowly. I wanted this to be pleasant for her. Little by little, I went deeper until I was all in her. Then I leaned down and kissed her as I stayed still in her. Letting her pussy adjust to my cock. We both started moaning into each other’s mouths. I was so turned on my hips began working in and out of her. Joanne’s moans became louder as her hips responded to my cock sliding in and out of her. Then, I don’t know where it came from, but I thought, is she on birth control? I asked her, and she nodded her head no. I was so turned on by now I couldn’t stop and just fucked her harder.
Joanne started pushing her hips up into me, and her body was reacting. I knew she was close. A few more thrusts, and I felt her body tense, her pussy clamped around my cock. A few more thrusts and I was ready, so I pulled out and shot my cum all over her stomach and tits. Fuck, it was a huge load, and she was covered. After spending time together, Joanne returned to the bathroom to clean up and dress.
We both returned to the party smilingly, looking like the cat who stole the canary. As we went swimming and relaxing on the chairs, I saw Mrs. D checking us out throughout the day. The party ended, and I drove Joanne home. Because of the day, both of us felt a new sense of closeness.
When I returned home, many neighbors were still poolside, but I could see Mrs. D was home. I parked my car and walked over to her place. She was sitting on her sofa watching some TV. She smiled as she watched me come in. Joanne is a beautiful doll; you hit a home run with her. I blushed and thanked her as I thought to myself, how awkward is it to hear the woman I’ve been fucking talk about my girlfriend.
Smiling at me, she put her hand on my thigh as I sat beside her, “So, how was she?”
“What do you mean, how was she?”
“Listen, baby, I know you better than any other woman. I know you two fucked today, so how was she?”
She picked up on my embarrassment.
“Don’t be embarrassed. I am happy for you, but I hope you made it special for her because it was her first time.”
I smiled at her as I responded, “You did teach me well, didn’t you?”
“Yes, I did, but I do hope you have something left for me; all those neighbors leering at me got me quite horny.”
“You know I always have something left for you.” I stood up and presented my hand to Mrs. D. As she took it, I walked hand in hand with her to her bedroom, where as always, we had a long wild fuck session.
My relationship with Joanne changed that day. We became very sexual from that day on, but no matter what, I always ensured I kept enough in me to meet Mrs. D’s needs as well.