Spending a weekend at my grandma’s was always fun, but one weekend in particular was unforgetable. My grandma lived in a 4 apartment building that she owned with her brother and his wife. They lived in the 2 downstairs apartments and rented the upper 2. This story occured when I was 16, I went and spent the weekend with her. I do not think I had ever spent the night at my grandma’s alone, always with my brother and sister there, but this time I was there alone. My parents had taken my brother and sister out of town, and for some reason I did not go, I can not remember now why.
After my parents dropped me off and I was settled into the spare bedroom, I quickly went to the ketchen. My grandma always had something good to eat. That is when she informed me that my cousin Sherry was staying with my great aunt and uncle next door. She was 16 also and was really my second cousin, but we always referred to each other as cousins. I had no idea she was going to be there, and really could care less. I was not very close with Sherry. She did not live near me. She went to another high school across town from me, and to be honest, I thought she was a spoiled brat. She was an only child. She use to tell on my brother and me, to get us in trouble. To me Sherry was always this short, fat, freckled girl cousin. She took all those dance and baton lessons that all girls use to take, and my parents were always being asked to come watch her at her recitals. I don’t know if my parents ever went. My mom probably went a few times, but thank goodness she never tried to drag us there. My brother and I use to say, we never saw her at our ball games. When my mom told us that Sherry was entering all those Lil Miss contests, my brother and I couldn’t believe it. No way did fat Sherry get on stage in front of a crowd! But, apparently she did. Even when Sherry reached puberty and started developing boobs, she was still just a short, fat girl with boobs, where belly stuck out further than her boobs, and when I saw her in a bikini, well, I still have nightmares.
I will admit though, I became interested when my mom informed me that Sherry had made her high school majoritte squad. Sherry’s high school was one of the largest schools in the state and they had so many hot girls that went to that school, and, I had seen their majorittes, they were hot! I just couldn’t see how Sherry could squeeze into a majoritte costume and appear in public.
I was in the ketchen when I heard my grandma yell and say Sherry had arrived. I went to the front of the house to meet her and see her mom and dad. We exchanged pleasantries and then I helped carry Sherry’s luggage to her grandparents apartment. I had to ask her how long she was staying, cause she had enough luggage for a month. She kind of laughed and said she was just staying Friday and Saturday. Sherry had changed some. First, she was actually pleasant to me and talked to me, instead of ignoring me. But, I could not tell that much about her physically, other than she was a little taller, but she was wearing baggy sweat pants and an oversized long sleeved white shirt, that she had the shirt tail tied, and she had her hair tied in two pigtails, and very little make up. I took her things to her room, told her we could get together later, and I went back to my grandma’s apartment and started watching TV.
About 4 o’clock my grandma came in to tell me that everyone was going to eat supper together. I said great, and asked her what time we were going to eat, because I did have to go for a run. I was wrestling and had to get in a run for my weight. She told me what time supper was, but also asked me if I could walk down to the grocery store and get a few things. I said sure, and then she suggested that I ask Sherry to go with me. I didn’t have to ask. Apparently the same thing had been suggested to Sherry. As I was getting up, she came into the room I was in and asked if I was ready to go grocery shopping. I said sure, and we set off.
Sherry had changed clothes into some jeans, shirt and was wearing a light jacket. She had also put on makeup and let her hair out of the pigtails and let her light brown hair loosely fall down to her shoulders. She had grown taller, to about 5’6″ and was not fat anymore. Her face was thinner and I have to admit, was actually pretty. I could still tell that her thighs were a little thick, but she had an awesome butt.
We left the apartment and started making small talk and just catching up with each others lives. She asked me how my wrestling was going, and that she kept up with me by reading the paper. I told her I was doing pretty good, and how was her year as majoritte. She told me it had completely changed her high school experience. She loved it and was having a great year, much different from last year. I half kidded her and said I guess she got asked out alot more this year than last, before I realized that might not have been nice. But she smiled and said “oh yeah, it is much better.” Then she asked me how Pam, my girlfriend, and I were doing. I told her we were great and then we arrived at the grocery store.
We walked around the store and got what was on our list. Sherry then said that she just loved this little grocery and asked if I had ever come down here before. I told her sure, that I had come with my grandma. But she wanted to know if I had come down by myself? Not being one to just shop, I told her no. She then told me that she and one of my other male cousins, who was also our age, came down here everytime they stayed with grandparents. Sherry then took me by the arm and said let’s get one more thing not on our list. I just followed and she led me to the liquor shelves. She pulled a pint bottle of vodka, looked in both directions and then stuck it in the front of her jeans and covered it with her jacket. She told me that she had done this several times. She also said that if this one girl was at the cash register she would sell liquor to you, but she did not see her today. We went through checkout and then headed back up the hill to grandma’s place. At first I expected at any time for someone to come running after us from the grocery store accusing us of stealing, but nothing happened. Sherry then said she should have asked me if vodka was ok, and I just said sure. I really did not drink. I had tried a few times, but especially during wrestling season I did not drink.
Sherry asked me if I wanted a swig now, and I told her, “no thank you,” and she said it was mostly for later after dinner, or maybe tomorrow.
When we got back to the apartment, Sherry and I helped with dinner and talked with our grandparents and then had a great meal. It was at the dinner table that I was now able to see another view of Sherry. She was not wearing the jacket any more and had on a button up shirt that I could now see her boobs had developed fully. In fact, the buttons on her shirt were being tested for their strength. I know I stared for most of the meal, but Sherry didn’t embarrass me, even if she did see me.
After dinner we helped clean up and then all went into my grandma’s TV room and watched for a little while. Sherry and I percervered as we knew they had their TV shows that the three of them watched. We also knew they would get sleepy early and then we could watch what we wanted to, and be alone to talk and probably drink.
Just as expected, after their last TV show my grandma and her grandparents headed for bed and told us to watch what we wanted to, and they also told us where some snacks were. Sherry said she was going to go change into her baggy sweats so she would stay warm, so she walked back to her grandparents apartment. I also knew, so she could get the vodka and better hide it from her grandma. She said she would be back before the next show started. I took the opportunity to go pee and brush my teeth and freshin up a little bit. I also made sure that my grandma went into her bedroom and turned out her lights, and then I went back into the TV room.
When I was channel surfing Sherry came back to the TV room. She had changed but not into what she had said. She was wearing a large robe and some house slippers, but I could see bare legs at the bottom of the robe, so she was not wearing her sweat pants. In her hands she had 2 glasses and some orange juice, and then she pulled the vodka from the pocket of her robe. She then asked me if I could go get some ice, so I went in the ketchen and got some. When I returned, Sherry was sitting on the couch, had the TV controls, and her robe had fallen open a little, just to show her knees and that she was not wearing anything long. When I put the glasses on the table in front of the couch, she leaned forward and poured the vodka and orange juice and as she did, the top of the robe opened more, and I could see that she had on her pj top and I could make out she was still wearing her bra. She offered me my glass and said, “cheers” and we took a drink.
I’ll have to admit here too, that it was strong and I almost choked and Sherry even asked if I wanted more orange juice. I manned up and said nah, but just sipped after that.
We cuddled up on the couch and started watching some movie, I have no idea what and we started talking again. Sherry told me that she just loved to come to her grandma’s house and wanted to know why I didn’t come as much as she and her other cousin? I told her that I had another grandmother and that I spent time at both, just never when she had been there. She told me that she could get away with murder with her grandparents and she told me some of the things she had done. She and my other cousin had gotten drunk several times, and had played truth or dare together and gotten pretty wild. She had even snuck out of the apartment one night, had her boyfriend pick her up and they had gone clubbing all night, then she snuck back in before they got up.
I just sat and listened. I hadn’t done anything like that. In fact, I was really not that wild and experienced as Sherry appartently was. Sherry then told me about her current boyfriend. He was a really good football player at another school and he had been on the sports page all fall. I also knew him because he was a pretty good wrestler. Sherry then shocked me when she said that he was the best built guy she had ever been with, that he was always horny, but that he misstreated her, and that she was almost positive he was cheating on her. Before I could ask how she knew and what did she mean, Sherry shocked me even more. She brought up our conversation that afternoon. Sherry reminded me I had said that my girlfriend and I were getting along great, then she wanted to know, “is Pam on the pill?” I was just silent. I had to collect my thoughts and not come across as a complete nerd, but I was a virgin, so I was honest and responded, no, I didn’t think she was.
Sherry turned and looked at me and replied, “oh you guys aren’t having sex?”
I know I swallowed hard and told her, no, we had not. She then kept asking, “oh then what did great mean?” How far have you guys gone? What have you done?
I tried to be cool and said that we were going slow. That we had talked about it and both agreed to wait.
Sherry cocked her head in an awkward way and bluntly asked, “you agreed not too?”
Before I could respond she said, “you are to hot and good looking to date her if she won’t put out. What have you two done?”
I about choked and told her that I had felt her boobs and she had let me finger her.
Sherry then wanted to know what she had done for me?
I swallowed hard and told her that she had given me a hand job.
Sherry then blurted,” have you two done oral?” I told her no, and she said,”oh my, she hasn’t even given you a blow job?”
I shook my head and she said, “oh baby, you need some help.”
I then got to talk and asked her,”when did you start having sex?”
Sherry didn’t even blink and looked into my eyes and told me, she lost her cherry her freshman year in high school at the first football game party. She then pushed me more and wanted to know if Pam was my first girlfriend and if she was the only girl I had done anything with.
That straightened me up a little bit. Now I could brag and sound worldly. In fact, Pam was not my first. I asked Sherry if she remembered the girl that use to live next door to us? She was also named Sherry, so she remembered. The next door Sherry was 2 years older than me, but we had grown up together. She also had a younger sister that was 2 years younger than me, and we had gone camping together in the hills around our house. I told Sherry, my cousin, no, that Sherry and I had gotten naked together and she was the first girl I had felt her tits and fingered her pussy.
Sherry wanted to know when that happened and I told her it was also in the 9th grade.
She was a junior in high school and we did things for about 2 years, before she left for college. Sherry looked at me kind of funny and just said, “you got naked with that hot girl and didn’t have sex with her?”
I know it must have been hard to believe, but I honestly told her, no, just feeling and touching.
I now remember noticing that Sherry was really enjoying asking me these questions and after my initial shock, I was enjoying talking about it. I had never had as open a conversation with a girl about sex as that was, and I was enjoying it.
Sherry, my cousin, now turned on the couch and faced me. She crossed her legs and pulled her robe over her legs, almost exposing a crotch shot, I looked, but no peek.
But I could really tell she wanted to hear the details. I told her how at first my neighbor would let me see her pussy, but not her tits, but then we got to where we get naked in front of each other. I then asked her when was the first time she had let a guy feel her boobs, and she told me when she was in the 6th grade. I immediately thought back and thought, ugh, remembering how she looked then. But Sherry could not tell what I was thinking, and she then asked, can you guess who it was? I thought and wondered, how would I know, then she told me, our cousin Al.
I know I had the most shocked look on my face and Sherry just laughed. Yeah, we use to play all the time. He was the first to feel my pussy too, and I actually taught him how to jerk off. That almost made me sick, cause he is the one that taught me how to masterbate! I was feeling so young compared to Sherry, and wondering now what they had thought about me.
I asked again, “you and Al have really done those things?”
Sherry just smiled, said yes, then turned, poured another drink and then slid back closer to me on the couch and we watched the movie in silence for awhile. I couldn’t tell you what we were watching, but do remember it was rather steamy, and when it did, Sherry would move closer to me. I even got so bold as to put my arm over her shoudler.
When the movie was over, Sherry turned to look at me, patted me a couple of times on my thigh and asked me if I wanted another drink? I told her no, “let’s save it for tomorrow.”
She just smiled but said, “you know we could get some more.”
Once again I felt so weird but wanted to be bolder. Her breaking the silence did help me, and I then spoke up. I said to her, “you know Sherry, you have changed so much in the last couple of years. To be honest, I didn’t think you were that cute when we were little, but now you are very pretty and very, very sexy.”
Finally I think Sherry blushed, and she said, “well, you have changed too, and you are so hot, that is why I am kind of surprised you have not done more with your girlfriend.”
I replied, “I haven’t changed as much as you, and as you can tell, I’m not as experienced as you, but you have made me not so shy about talking about sex.”
Sherry kind of looked down and said,”well, I think you have changed and I have liked talking with you too. Would you like to do more than talk?”
I should have been shocked, but I wasn’t, I was actually expecting it, and was going to say something if she didn’t. I even got bolder and said,”yes, and even asked, would she help me?”
She got a funny look on her face and asked,”help you?”
And I said, “yes, tell me or show me what a girl likes and what I should do.”
Sherry said,”I think you know.”
I replied, “no, I really am not sure.”
Sherry said ok, and that this could be fun. She then asked me to go check and be sure my grandmother was asleep. I got up and tip toed through the apartment and checked to make sure her door was closed, and I went back to the TV room and closed the door behind me. Sherry was still on the couch in her robe, but had poured her another drink. She asked me if I wanted another and I told her no, I wanted to remember what we did. That made both of us laugh. Sherry then asked me if I had a robe like hers, and I said no, that I just slept in my boxers and didn’t bring a robe. She said ok, but we had better listen in case someone came in, even her grandparents coming to check on how late it was. I agreed and sat down beside her.
Then everything felt so awkward and Sherry asked, “now what?”
I know I blubbered, but said, well you have changed the most in your boobs, and I know you have seen me staring all evening.”
She just stopped me and asked,”do you want to feel?”
I just nodded and she loosened her tie belt around her waist and let her robe open slightly. I moved my hands to open it more, to see that she had a baby blue cotton pj top. I moved my hands and cupped her boobs over her bra and then realized that she was huge! I commented, “oh my god, Sherry, you are built.” I even kidded, “how do you get these in your majoritte outfit?”
She giggled, “it takes a little squeezing.”
I fondled her boobs, but wanted to actually touch them. I then moved beside Sherry and kind of behind her. She realized what I was doing, so she pulled her robe off her arms, and then pulled her top off, all the while watching the door, which told me she was as nervious as I was. I put my hands up and unhooked her bra. She let the bra slide off her arms and her tits plopped out. As Sherry was putting her pj top back on, I took her bra, held it and noticed that she was a 36D. That made me more excited. Oh what a change from my girlfriends 34B. Sherry had her top back on and then put her robe back over her shoulders and turned towards me and smiled. I stared right into her eyes and pulled her top up to expose her humongeous boobs. I then dropped my glare and took in the view. Her tits drooped from their weight and like her face and legs, her titties had freckles all over them. I also took in how big her nipples were, bigger than quarters. She broke the silence and said, “go ahead and feel them.”
My hands moved up and took a tit in each hand. They were both so soft but heavy. So much different than the small titties that I had felt before. I touched them, stretched my hands to see how much I could hold, and then squeezed them. I then asked Sherry, “does this feel good to you?”
She looked me right in the eyes and said,”oh yes, and you can be rougher if you like.”
“Rougher?” I looked at her. “I thought your boobs are all soft and tender, what do you mean rougher? Do you really mean that?”
“Yes,” she said. “I mean what you are doing feels so good, but when I get more aroused I like it to have my boobs squeezed more and even pull on my nipples. Right now just take your fingers and play with my nipples and take them and roll them with your thumb and finger.”
I did as I was instructed and my dick got harder than ever as her nipples got as hard.
She let me play with her tits for 10 to 15 minutes. We finally ended up looking into each others eyes and Sherry then asked, ” is there anything else you are interested in?”
which made us both giggle.
I stammered and said, “ugh, I have a few more interests.”
Sherry then said, “but, first it is my turn, I want to see how you have changed.”
I knew exactly what she meant and I stood and unbuckled my belt, unbuttoned my jeans, unzipped my pants and then pulled them down and stepped out of them. I had a tent in my boxers and I turned to face Sherry, as she was still sitting on the couch. She then asked, “would you pull your boxers down and let me see?”
I put my fingers under the elastic at the top of my boxers and pulled them down, first revealing my thick dark brown pubic hair over my crotch, then my rock hard cock popped out and bounced off my stomach, and then stopped still pointing up towards my tummy. I pulled my boxers down to my knees, not wanting to take them completely off and looked at Sherry stare at my crotch. She then told me to cup my balls, and I did as she asked. Then she said,”oh you have changed,” and smiled.
I then pulled my boxers back up and Sherry pulled her top down over her tits and reached and picked up her bra and put it in the pocket of her robe. She said,”that might have been a little hard to explain if I had left my bra in here and forgot it.”
I agreed and half laughed, but looked around to see if we might be leaving something else. Sherry then covered up her upper body, pulled the tie belt a little higher than her waist, right under boobs and tied it back, but let the bottom of the robe open a little more. I could see what she was doing. She then slapped the couch right beside her, indicating for me to sit beside her. She then slid down the cushion of the couch and put her feet on the floor and almost lying down but still resting her head so she could see. She knew I was excited so she pulled open her robe revealing her legs and the matching baby blue shorty pj bottoms that went with her top. My eyes were glued to her actions. She pulled her pj top up a little and I saw her belly button. Sherry was watching my face and moved her hands to the top of her panty bottoms. She then raised her hips slightly and slowly pulled her bottoms down. Her freckled tummy was so cute, and when I first saw her tan line, I saw the first whisps of her curly pubic hair.
The panties went down and I saw her pubic mound covered in a trimmed light brown triangle patch of hair. Then she cleared her butt, she put her hips down, and her legs went together, but I could see the top of her slit and saw that it was baby smooth. She pushed her panty bottom as far as she could, then she asked if I could help, so I took them and pulled them off her legs and then handed them to her, not wanting those left.
Sherry took them and put them in the other pocket of her robe. She laid there with her privates exposed and then said, “go ahead, feel me.”
My hand was shaking I remember, but I moved it to her bush and softly felt her pubic hairs, then slid my hand down between her legs. As I did so, Sherry spread her legs and let me touch her pussy. I then looked into Sherry’s face and saw that she had her eyes closed now. I looked back to her crotch and watched my hand touch the inside of her thighs and then her puffy pussy lips. Then Sherry spoke,”feel how wet I am.” I then fingered her lips, and found her opening with my middle finger. I could feel the heat from her crotch and my finger easily slid into her pussy. I pushed it inside her and held it as deep as I could push, and with the palm of my hand was rubbing the top of her slit.
Still with her eyes closed, Sherry whispered,”now slide your finger in and out of me,” and she said, “finger fuck me.”
I don’t think I had ever heard a girl say that word, much less in this situation, but I knew that Sherry was enjoying what we were doing too, so I began sliding my finger in and out of her pussy and I could hear her breathing change. Then she said, “put 2 fingers in me.” Now I moved so I could look down and see her cunt lips engorge my fingers. I put two fingers to her opening and slid them in. Now I realized she liked it faster, so I went as fast as I could. Sherry was now taking short breaths and then I notice her move her hands to her tits and she began pulling on her nipples through her pj top. I don’t know why I didn’t cum, but I was really just thinkig about Sherry and fingering her as fast as I could. Then, she moved one of her hands and grabbed my wrist of the hand I was fingering her, and then she clamped her legs together and I felt her whole body quiver. It was fantastic to watch her shake like that and to think that I had done it, made me more excited. Finally, Sherry opened her eyes, smiled and then said,”and now you have seen a girl have an orgasm.”
I smiled back at her and she raised up and for the first time, kissed me on the cheek.
She then pulled her robe together and then said,”ok, now let’s take care of you.”
I then spoke up and said,”wait just a second. I’m not sure what I just did. Can I please ask you somethings?”
Sherry just smiled and said, “sure. What you just did is made me cum. You brought me to orgasm.”
“Ok, I understand that, but what felt so good?” I asked.
Sherry replied, “oh, well, kneel down here,” and I knelt down in front of her and she sat on the edge of the couch. She pulled her robe open again and then spread her legs. Now I had my clearest view of her pussy and it was so beautiful. Sherry put her hand on her pubic hair and said that she had loved the way I had touched her there and had run my finger over her mound and through her pubes. She even said that she didn’t know she was so sensitive there. She then took her fingers and spread her pussy lips and showed me exactly where her hole was and where my fingers had gone. I could see how her pussy lips were swollen and darker colored that the inside of her legs. She said I had been so great fingering her, but that there is one more place I should know. I had kind of touched it, but not much. She then spread her pussy and used her finger and pointed out her clit at the top of her slit. “This she said is the most sensitive.”
“Oh, sorry I missed that.” I was honest and said, ” I didn’t know that.”
Sherry then got this sly little smile on her face and said, “you are wanting to learn aren’t you?”
I thought she was talking about my education on the clitoris and said,”yes I am.”
But she meant different and asked,”are you up for an education on oral sex?”
She knew I was up for it and leaned back on her elbows and said,”I am ready to teach.” I must have had a questioning look on my face, so Sherry said,”lean in and kiss my pussy.”
So I leaned down and the first thing I noticed, of course was her musky smell. I wasn’t sure at first if it was a pleasant or disgusting smell, but was so excited that I was going to get to eat my first pussy, I quickly just didn’t notice it. I put my lips to her smooth swollen pussy and kissed. I could feel the heat in her lips. Then I heard Sherry say, “lick it. stick your tongue in my pussy.” I pulled back a little, mostly to look at how wet her pussy had gotten, and then I stuck out my tongue and licked her slit. Then I put my thumbs up to her pussy, peeled them open and then stuck my tongue as far as I could up inside her. Sherry then grabbed me by the hair and pushed my face in deeper. Then she pulled my face up and she whispered, “lick and suck my clit.” My tongue slid up her slit and I felt for her little nob and when I felt it, I licked and licked. Sherry was pulling my hair more, so I knew she was enjoying. My tongue was actually getting tired, so I trapped her clit with my lips and then began sucking on it like a lollypop. That was it! Sherry jerked and turned slightly side ways. I sucked harder and I felt her legs tighten against me and her body shook all over.
When I finally felt her body go limp, I stopped sucking and looked up into her face and said,”how was that?”
Sherry put her hand on her forehead and said, “you are a great learner.”
“Good teacher,” I said.
Sherry then looked at the time on the TV and said,”oh baby, look how late it is! It is now your time. Can I give you your first blow job?”
You know my answer. I sat on the edge of the couch like Sherry had and my dick was sticking out of my boxers. Sherry took it in her hand and started with a hand job, then she asked if I could pull my boxers down, so she could play with my balls too. So I stood up and pulled my boxers off and sat back down. Sherry took my cock in her hand again and tried her best to look into my face as she stuck out her tongue and licked my cock head. That sent electricity all through my body. Sherry then got to work. She cupped my balls with one hand and held my dick with her other. I watched as her head began to bob up and down as she sucked my dick. I could feel her tongue licking and rolling around the head of my cock. I could not help it, but bent over a little and cupped both of her titties. Sherry realized what I wanted, she stopped a second, opened up her robe and then went back to sucking my dick. Now I could fondle her huge tits over her cotton top. With all we had done, it didn’t take long. Sherry sped up and was playing with my balls, where she could feel my cum building. When I heard her go,
“mmmmm,” I started pulling harder on her tits and found her hard nipples. Then I told her, I’m going to cum, but to my surprise Sherry kept sucking. I exploded in her mouth and she took it all. She stopped bobbing on my cock and used her hand.to keep me cumming. Finally I just collapsed and she came up with a smile on her face. “How was that?” she asked.
I replied,”unbelieveable.”
With that she said she had to go back to her grandparents and that she would see me tomorrow. She gathered up her bra, pj bottoms, and vodka and left.
I’m not sure if I got much sleep that night, but I jumped right up the next morning. I was eating my favorite breakfast of pancakes in my grandma’s ketchen when Sherry came bopping in and said, “hey, how is sleepy head doing?” She said that she had been up and already eaten breakfast.
My grandma then asked us what we were going to do that day and we each looked at each other and said we didn’t know what we were going to do. I did have to get in some running, My grandma then said it was suppose to be a cold and rainy day today, that I had better run early. Grandma then said she and Sherry’s grandparents were going to go out a little while to buy some supplies for cleaning the upstairs apartment carpets. I asked, why did they have to clean the carpets? Why didn’t the renters clean them. That is when she told us that the people upstairs had moved out and they paying someone to come and clean next week. They just had to supply the materials.
Sherry and I immediately looked at each other and smiled.
I then went and put on my running gear and took off. I didn’t run far, in fact, just to a place where I could see my grandma’s car. When I saw them pull out, I went running back to the rear of the apartment complex and went up the back steps to the second floor apartment. I tapped lightly on the door and Sherry opened the door and let me in.
I slid in the door, closed it behind me and we immediately took each other in our arms and hugged and for the first time, passionately kissed. We then held hands and started searching through the apartment, I don’t know what for, but snooping around.
We ended up back in the living room, which had a big picture window that looked down on the front of the building. It was higher than anything around and had a great view.
Sherry gave me a cute smile and asked what would I like to do now?
I smiled back and honestly told her I would like to play with her boobs and pussy again.
She said that sounded good to her, if she got to play with me. Sherry was wearing a running suit, like she was going to run with me. She then moved her hand to the zipper on her jacket and pulled it down showing me she wasn’t wearing a bra. I could just see the inside of her boobs.
I leaned down, untied my running shoes, kicked them off, and then pulled my jogging pants off. When I stood up, Sherry could see that I was wearing bikini underwear and she jokingly told me, hey, did I steal a pair of her panties?
I laughed with her and replied that now, that my “boys” need support when I’m out there bouncing them around! But right now, it was way too much support. My dick was popping out over the top of my undies, and I quickly pulled them off. Now I was naked from the waist down, except for my socks, and a sweat shirt on. Sherry was still in her jogging suit, just with the front unzipped. She stepped to me, put her hands on my bare ass and pulled me tight into her hips, and we French kissed again. Then she moved her hands up under my sweat shirt, pulled it up and she then felt my nipples, moved her face down to my chest, kissed my nipples and then bit me. It sent sharp pain through me, but then it felt good. We kissed and I moved my hands and fondled her titties. Then I pulled one hand out and rubbed her between her legs. She let out a nice moan, and I knew she was hot. She took my face in her hands, kissed me and asked if I would like her bottomless too?
Of course I nodded and I stood back and watched as she pulled her jogging pants down, to reveal her black bikini panties. She then peeled the panties off and I got to once again see her bush and pussy. She stood there for a second and I then took her in my arms again and we kissed and hugged. But then I realized my cock was on her tummy and my balls could feel her pussy hair and slit. Without breaking our hug, Sherry moved her hips back a little and trapped my dick between her legs and then pushed her hips up tight against me again. It felt wonderful!
After some passionate kisses and groping, Sherry broke our kiss, laid her head on my shoulder and then whispered,”would you like to put your cock inside me?” She went on to say she would understand, since it was my first time, but that it was ok with her.
I’ll admit, I had to think about it. I had talked about doing it the first time with my girlfriend, and I immediately thought how I could lie to her later, but my dick was just too hard and I was thinking with the head between my legs.
I said yes, I would like that, but where could we go.
Sherry said we should stay there because we could not get caught. But then it hit me! I didn’t have a condom. Sherry then told me, not needed, she was on the pill and it had worked with her boyfriend.
So I said, where did she have in mind.
She said if it was ok, she had a position that really felt good to her and knew I would enjoy also, so I said, let’s try.
Sherry then led me to the big picture window and told me she could also watch to see if our grandparents returned. She requested first, could I get her a little more ready?
I said of course, “what should I do?”
Sherry put her hands on the window ledge and bent over slightly. She then said, can you finger me, get me wet and maybe eat my pussy?
I didn’t need a second invitation. I kneeled down behind her. She spread her legs a little more and I moved my hand and cupped her pussy. Then I fingered her pussy lips, felt a little wettness, and then stuck my face between her legs and licked her pussy until she was gushing. I think she had a mild orgasm as I ate her.
Sherry then said,”it’s time baby. stand up and put your dick in my pussy. I want to feel you inside me.”
I stood up and took my cock in my hand and first pushed it down the crack of her ass.
Sherry reached down with one hand and took my cock and guided it to her fuck hole and gently pushed up. I put my hands on each side of her hips, bent my knees slightly and shoved my hips forward. I felt her slickness and then realized my dick had popped inside her pussy. I looked down and saw her curved ass and could see part of my dick still not in her. I pushed my hips and pulled her hips into me and felt my cock slide into her tight pussy until my stomach was tight into the crack of her ass. When I was all the way in, I held her hips tight and let her squeeze my cock with her pussy muscles. Sherry moved her hand and squeezed my ball sack, then moved her hand onto the window ledge and braced herself. I withdrew my cock and then started humping her faster.
Sherry was now moving her hips and our rhytem was going faster and faster. But then Sherry almost stopped. She was breathing hard, but then she spoke and asked,”can you cup my tits? They are bouncing and rubbing the inside of my jacket and it doesn’t feel good.”
While holding my cock up inside her pussy, I moved my hands from her hips to the front of her jacket, opened it and cupped her tits. When I pulled my cock back to start fucking again, Sherry spoke again,”wait, that isn’t such a good idea. If someone looks up here they can see my tits. Can you come under the jacket?”
I said,”of course.”
I put my arms around her waist and let Sherry zip her jacket back up, Then I slid my hands under it from the bottom and cupped each huge boob. With tits now to hang on to I start humping Sherry again. It didn’t take long for us to get the rhythm again. I still remember how wonderful it felt to have my dick up inside her, and I loved fucking her in that rear standing position. My girlfriend never even let me try that after we started having sex.
We were both about ready to cum. Sherry spoke first and said,”squeeze my nipples now.”
I then spoke and asked Sherry once again,”Sherry, I’m gonna cum, are you sure you want me to cum inside you?”
“Oh yes,” she answered. “Fuck me hard and cum in my pussy.”
That was all it took, I warned her,”I’m cumming!” I pumped a couple more times and then pushed my dick all the way in and the spewded my cum all up in her pussy. Sherry either started cumming too, or just knew squeeze with her cunt muscles. I just held her and kept my dick up in her pussy and fondled her boobs.
As we both felt my dick start to slide out of her cunt, Sherry told me to reach down and pick up her panties and when I pulled out, catch my cum with them. She said she would wash them before she went home. I could barely reach down, but picked up her panties, slid my dick out and put her panties between her legs to catch the jism.
Then Sherry blurts,”just in time! Grannies car just pulled up.”
I said, “are you going to be ok?”
And she said “sure.”
Sherry pulled her warm up pants back on, and I quickly got dressed again and went out the back and got in my run.
I wish I could tell you of more fun that Sherry and I had, but that evening and the next day we were always with others and didn’t have another opportunity. But I’ll never forget that education I got from my cousin. 2nd cousin!