1984 The Summer I Became Jaime….

This story is fictional, It’s about A 14 year old boy who wants to be just like his two older sisters. Except Jaime takes it a bit further…

I had just got out of school and my summer vacation of 1984 has started and my goal was to make some extra money. So I came up with an idea to mow my neighbors lawns, But I know I needed a reliable push lawn mower and I heard of a man who rebuilds them, but money was my problem.My Father nor my Mother would give me the money to get one, Because I was kinda a girly boy, and they always think I”m going to get hurt. Plus I rarely see them, they work out of town most of the time and I was not really sure what they did for a living. I was told by my two older sisters they are in sales. I have to say I”m lucky having two older sisters, Because they are too busy with themselves.And I can usually steal some of their clothing , plus my one sister wears the same size shoe as me. The next morning I got up and had my breakfast, I waited until my sisters left for the beach for the day. It gave me time to rummage through their closets,and find something to wear that might make me look passable as a girl. Maybe pretty enough for Mr. Collins,The gossip I had heard was he was into younger girls and sissy.So maybe if I looked my best and pass as a girl, we could make some kind of a deal.I then ran myself a bubble bath and shaved everywhere I had hair growing. After that I dried off, I then applied lotion all over my body. Sprinted a little perfume, Then I pushed my tiny penis and balls up inside myself, while keeping my legs crossed I put on a pair of tight panties to keep everything tucked, while going through my mom”s things I found a padded push up bra, She is a C cup, So I had to cut up a old pair of pantyhose and fill the loose space in the bra with them.My sister had a old pair of silky type side cut gym shorts that were kinda tight on me, I was surprised how good they looked. Then one of her Izod collared shirts, which was a lot tighter with the bra on and a Pair of white keds tennis shoes with bobby socks.My hair was already long with a bit of a curl, I usually kept it in a ponytail. So I let it down and fixed it, too look as pretty as I could. Sprayed it down with a big can of aqua net. After I was all done I went into my sister”s room and look in her full body mirror. I was very surprised how cute I looked. I said to myself well let”s go do this..

I then got on my bike and rode over to Mr. Collins home and knocked on his door. I was very nervous but needed this mower, After a few minutes he came from around the back of his house. He said what can I do you for you young lady, So with my best girly voice I said … Good Morning Mr. Collins, I need a good reliable push mower. He gave me a long look and said.. what”s your name young lady? I smiled and held my hand out, I”m Jaime, Well little Jaime, ( at 14 I was only 5″ 2 bit curvy for a boy and had a more of a girl shaped body)I have to say you have very soft hands. I kinda blushed and said, Thank You while making eye contact and biting my bottom lip. I can see it kinda excited him,He coughed and pulled his hand back, trying to hide being caught off guard. Smiling he said, I do have few of them but it”s going to cost you fifty dollars Lil Lady, Well I don”t really have any money but would you be willing to do some other kinda payment plan.He stood there for a few moments and kept looking me up and down.I knew what was on his mind.( You know I remember my sisters talking about some things they did to get what they wanted, I would act like I was listening to my headphones, But I was really listening. I mean my sisters are not easy or slutty, But I understand sometimes young ladies do things to get what they want and then move on.Anyway, Back to Mr. Collins and his noticeable Boner.He then said,What do you have in mind.( Mr. Collins was a black man about 6″2 and in pretty good shape for a man in his late fifties, divorced and lived alone). I made eye contact and moved toward him and said, Well you did say I have very soft hands,Then I moved closer and pushed myself against his khaki shorts, feeling his rather large cock against my lower belly.Being very nervous I rubbed my hand over his shorts, feeling the outline of cock. He gasped and said, Whoa now!! How old are you… I said, old enough to jerk you off and let you finish on my face.After I said that, I could see how excited he got.

He started looking around and said, Your serious, Biting my lower lip again, I said MMMMhhhmmm. He then said follow me to the shop, I know I was taking a chance and things could go downhill not knowing this man that well.But for some reason I felt like I was more in control than him.We went around back and entered his work shop, After entering he pointed and said there is three
mowers, Take your pick,After you deliver your part of the agreement.I noticed he had a older leather couch against the wall.I said, lets have seat..point with my head and puckered lips.He sat down dead center of the couch, at the same time he grabbed my hand pulled me beside him. At that moment he went in for a kiss.. Stopping him with my hand in his face … I said while smiling, No kissing just let me jerk you off… OK Daaaddy. The moment I said that I could see his cock jump in his shorts,I then rubbed my hand over his shorts. He then unbuttoned his khaki shorts and unzipped them, I then reached inside his shorts and grabbed his 8 inch thick cock and pulled it out. I was amazed how relaxed and natural how it felt and could feel how moist my mouth got staring at it. Mr. Collins gave out a big gasp and said… My God your hands are so soft.. I smiled and started jerking his cock slowly, Then in my best sexy girly voice, I said.. You like that Daddy… Yeesss he said. So having a dick myself(even though it was very small and many times wish it was gone, I still knew exactly how to jerk it so it feels good)I made sure I pulled up the lower skin so it could go over the head of his big black cock. After a few awhile he started moaning under his breath, I knew he was close.. So I quickly removed my hand, drawing up all the saliva I could I spit in my hand, then I turned my hand backwards and slid it down over the head of his cock with a tight grip.Jerking him off this way drove him over the edge. Within a few more minutes I could feel his cock start to swell and his breathing getting heavier.Under his breath I heard him say … I”m cumming. I then switch my hand back the other way and while holding on,I got on my knees and opened my mouth, aiming his cock at my face. His eyes got bigger and and groaned deep and it seemed like in slow motion, I could see a blob of creamy Jizz coming right toward my face. I closed my eyes and felt it cover my whole face and just a tiny bit found my lips.I could not resist and licked my lips..OMG it tasted so good.It seemed like forever before the shots of cum stop hitting my face.I slowly opened my eyes and I could see Mr. Collins laid back with his big black cock laying to the side of his open shorts.His eyes were closed, I then said..was that good enough Daaaaddy..He then open his eyes, at the same time handing me a handkerchief to wipe my face, while wiping my face off.. He said.. Lil Lady take your mower and this never happened… You understand!!! After finishing wiping my face off, I said… Not a word.. But I do need something else, And what would that be Jaime… I need somewhere to hide my mower, So my mom or dad will not know I have it. He then said just come by whenever you need it and then bring it back here.. No strings attached… For some reason I knew that was not true… But I agreed.I left and on the way back home on my bike… I felt like I had power over a middle aged man and he seen me as a sex object and it felt good…..

I added a pic of myself, I know I”m not that pretty… but at 14 I tried. Please be nice

🔞 Candy.AI 🔥 AI Sex Chat - Roleplay, Erotic Stories, Try for Free 🕹️

Please, Rate This Story:

(average: 4.25 out of 8 votes)