Introduction

My name is Blair Conner, and I went to Vero Beach High School in Sebastian County. I was on Summer break in 1984 when I got into trouble big time. My mother insisted I write an accurate and honest account of that summer. It is difficult to recall all the details but let me provide a little background first.

I have reddish blonde hair, pretty blue-green eyes, an upturned nose, a few freckles, and people say I have “resting bitch face” because my natural expression is that of a bitch. That isn’t really true. I can smile. I just choose to look this way.

I suppose if you wanted to compare my appearance to a famous person a lot of people said I look like Molly Ringwald from Sixteen Candles and the Breakfast Club. She looks very stuck up, has the same kind of hair, and always looks like she just sniffed someone else’s fart.

It all began when my cousin Eddie came down to visit a week earlier.

NOTE: This is all detailed in Naked on Summer : Sissy Summer School

He, like most of my family, has the trademark red hair, and smirky expression of a know it all. He spoke with a lisp and had a very effeminate quality that made me instantly dislike him. I didn’t like many people back then and even people I did like it was generally only conditional on what they could do for me. I should clarify that it wasn’t conditional on what they HAD done for me in the past. I only cared about what they could do going forward.

He complained when my Mom insisted he strip at the public showers to wash off at the beach with my brothers Buddy and Lewis. They were all little enough that nobody out here cared. My cousin Eddie had some pubic hair, but he was hardly developed, and he made a big stink out of it.

My Mom used to make me strip off when I was little but as soon as I developed boobs that all stopped. I also didn’t like to play in the water anymore, so it was never much of an issue.

I should mention that my Mom was raised in a very strict household by an Ex-Marine drill instructor. My Grandfather was a member of the religious group “Children of God” in California during the 1960s, and my Mom was raised in a farm commune with her brothers and sisters. She used to talk about ‘flirty fishing’ like it was fun.

She and her sister would go out and tease and flirt with a young man in order to get him to come to church with them. She talked about her upbringing a lot, and half of the time I didn’t believe some of the things she told me and the other half I really didn’t listen. I just knew that my Mom was very opposed to raising me the same way, and I had never met my grandparents or much of my family.

Her father was a stern disciplinarian though, and my Mom believed profoundly in corporal punishments and corner time. She wouldn’t hesitate to pull my panties down around my ankles and spank me when I was a little girl, but again all of that stopped almost the moment I sprouted breasts. My Mom believed very heavily that all adults should be responsible for kids and expected me to be respectful to all adults at all times and listen to them. She would never have thought twice if our neighbor Mrs. Hannigan washed my mouth out with soap for cussing.

However, for the last two years or so, I was on easy street after I reached puberty because my Mom became for more lenient with me. I felt like we were almost sisters in that I could tell her anything and joke with her. My Mom has a stern side, but she also likes to laugh and is very playful.

She likes to party with her friends at local bars and is very adventurous. They work together at my high school.

I could boss my little brothers Buddy and Lewis around. When I had to babysit them I ruled with an iron fist. The only problem was they were too stupid to be of any use cleaning up the house or doing any complex chores. Buddy and Lewis are like chaos personified, and they just ran around creating messes and having a good time. My Mom was strict with them but not as strict as she was with Eddie.

She took a particular interest in my cousin when he came down to visit. He is her sister’s son, and I suspected she missed her sister. They had been very, very close and now they seldom ever saw one another. I think Eddie reminded my Mom of her sister and she wanted to ‘fix him.’

I can’t really explain this next part very well, but at some point, Eddie became “Jenny.”

I had purposely got Eddie in trouble. I can’t even remember why I did it. I had let him sniff my panties and then set him up so that my Mom would find out he did it. I also put suntan lotion on him in order to give him a boner and then screamed to my Mom that he was a pervert. In my defense, he probably did a lot of pervy stuff leading up to that and had been caught peeping on me while I changed.

I should mention though I waited with my bare back to my open window for a good long time for him to finally notice me and subsequently get caught staring at my body through the window that just happens to be near my Mom’s sliding glass door in her own bedroom.

My Mom decided to punish Eddie by making him wear the panties he sniffed. That led to her deciding to feminize him in what she called “Sissy Summer School.” She said it would teach him to respect women and stop being such a total pervert. I thought it was hilarious and wicked.

My Mom called Buddy and Lewis in and pointed at Eddie and said, “This is Jenny now,” and they both pretty much shrugged and accepted it as gospel.

I was shocked by how quickly Jenny adapted to living as a girl. At first, I had to teach her how to put on makeup and pick her clothes. I taught her how to look like a total slut instead of all the techniques that look good. However, despite that, Jenny made a pretty cute little girl and wore her curly hair in pigtails.

Mom even let Jenny sleep in my room. I quickly arranged a situation where Jenny would get in trouble for peeping on me to get her kicked back out. However, my Mom’s solution was to put the little troll UNDER my bunk bed and tie her wrists to the bedpost.

I had no problem with that. I would even wake up sometimes in the middle of the night and fart on him or put his hand in a bowl of water just to fuck with the little brat, and he didn’t even notice.

My Mom made him “milk” himself frequently by jerking off and tied a pink ribbon around his balls we could lead him around the house with. She never watched him jerk off, but she did make him throw away the cum in a tissue.

You could lead Jenny around the house by the ribbon like a little puppy. Jenny liked it, and sometimes my Mom would make me walk her up and down the street to practice walking in girl’s shoes. I began to see Jenny as a girl, and so did all the kids in the neighborhood. They thought Eddie had gone back home and she was his twin brother. It was lucky for Eddie he had that lisp and high voice because he sounded more like a girl than a boy anyway.

I could take my frustrations out on her, and she was smart enough to be able to do the chores around the house. The problem was that she seemed to enjoy it all. The meaner I was to her the more she liked it. I even stepped right on her balls once in front of my friend Julie. I treated her like a puppy dog. I got her in trouble. I called her names. I ordered her to kiss my feet.

The meaner I was to him, the more she thrived and the more he learned.

My Mom started to get a deeper appreciation for how quickly she was learning, and I have to admit I was jealous of the attention on some level.

I should also mention that any time I babysat when my Mom went out for the evening, I would bring over boys. I had been leading these particular boys Jack and Bruce on for months with my friend Julie. I would make Jack like me and then play Bruce against him and pretend to like Bruce more. I would promise sex if they did things for me and then say what they did wasn’t good enough and only let them finger me or suck their cocks.

I had them on an emotional rollercoaster and wrapped around my finger nice and tight so they would do whatever I told them almost as obediently as Jenny.

One night I got very drunk on wine coolers, and I threw up and passed out in the bed. I let my cousin go down on me that night, and I have to admit I did enjoy it. He was persistent, and with a little direction, he was capable. I wasn’t going to tell him that or encourage him to do it again but if I was ever lonely or bored I was planning to pretend to be drunk again and let him go downtown on me.

I also made him stick a hairbrush up his ass, spanked him, kicked him in the nuts, made him jerk off in front of me and eat it. Just about anything I could think of, and he did it all without complaint. If I am completely honest, I really enjoyed and admired that about Jenny. Jenny liked eating off the floor so much after I made her do it that she asked my Mom if she could. My Mom didn’t think Jenny was serious, and she suspected I had been making her do these things, but she agreed to it. My Mom told me this story I thought was bullshit about one summer when she was disciplined really hard by her father, and he made her eat off the floor. I only listened to part of it, but it sounded like an exaggeration she was telling me to scare me into behaving myself. She didn’t threaten to make ME eat off the floor or anything. In fact, if anything she confirmed she didn’t want me to go through what she did with her own father.

One night things all came to a head when I threw a very large party that got very out of hand. I invited over a few girls and way too many guys. I didn’t want too many girls because I wanted the focus and attention to be on me. The girls I did invite I knew weren’t as hot as me. There was Julie, my best friend, and often most bitter rival and then Mandy who is just a regular rival. Jack and Bruce bought this old car salesman to the party because he had dope and booze. He brought this girl Betty from my school with him. She was known as the biggest slut in school even though she was still a Freshman at the time. She is also extremely hot and has huge tits. I was instantly jealous of her because she just made the party all about her, and I wanted it to be all about me.

It was like she didn’t even try either. She just walked in and flicked a little bit of her blonde hair and shook her tits and suddenly the record on the record player skipped and played her groove instead of mine.

I started drinking and started thinking of ways to get the attention back on me. I humiliated Jenny by making her strip at the party just to prove I could do it. It only made people think Jenny was cool. I made Jenny bark like a dog and sit up and beg to humiliate her farther. Julie and Mandy helped by playing fetch and making Jenny roll over and beg. Betty called me “Adolf Titler,” and everybody laughed at me. I felt like Betty and Jenny were ruining my party although in retrospect I realize it was me who was ruining the party.

I held a spin the bottle game that I knew would let me make Jack extremely jealous by making out with any hot guys at the party, and if it landed on a dweeb, I could always pass.

However, Betty upped the stakes of that game when she suggested we “At least play for blowjobs.”

I played it off like it was no big deal and said, “Slutever,” but no one heard my play on the word “whatever.”

I should have said no at that point, but I am very competitive. All the girls lined up and spun the bottle. All the boys were around the bottle so it would not land on any girls. Betty went first, and she started sucking this guy’s dick right in the living room like it was nothing. I pushed Jenny in next, and I felt a little bad when the bottle landed on the car salesman, but Jenny went to town on him in the living room too. She looked all doe-eyed and innocent first, but by the end, she was over there lapping up the cum with Betty and kissing it back and forth. It was so gross.

Anyway, I made all the other girls go before me so that I could get the bottle to land on Jack. However, Mandy cheated and spun the bottle just hard enough it landed on Jack.

I didn’t want to play anymore. None of these other guys had done anything for me, and I really wasn’t interested in sucking their dicks for free. What would that do for me?

However, the frustrated boys insisted, and before I knew it, Julie and I were getting groped and touched and fucking them. It wasn’t exactly against our will. We were goading them and teasing them, but I didn’t expect them to start fucking us from the front and back. Most of them used condoms but that night several guys I barely even knew fucked me from behind while others fucked my face and they lined Julie and me up and fucked us together titty to titty. Julie and I made out in front of them and got fucked like rabbits all night long. Around 2 am when most of the guys were spent I even included Mandy Sonneborne and started kissing her and letting her go down on me in front of the guys that were still there to entice them to get hard and fuck us.

When I woke up, I was covered in spent condoms and dried cum from boys I barely even knew. I think Mandy had drawn a penis on my face with a marker. We both wrote dirty words all over the house in marker and trashed the house in a frenzy at the end. I was really high and drunk, and Mandy and I were basically hate-fucking each other around the house.

My Mom found me naked in the living room. I had planned to wake up Jenny and make her clean it all up before my Mom got home, but I must have passed out. Jenny had cleaned up for us before, but a lot of stuff was broken and permanently damaged. We burned holes in the carpet and the couch with cigarettes and stained the carpet. My Mom was super pissed because we rent this place, and the landlord is a total cunt and lives next door.

I didn’t know what to do when my Mom confronted me. I tried to act innocent at first and say that I was manipulated by Mandy into throwing the party.

I tried to blame my jealousy towards Jenny for why I did it. I tried a couple of my normal deflections, and that didn’t work this time with my Mom. I knew she wasn’t buying any of that, but I tried every trick I knew to get out of what seemed like the inevitable decision of my Mom to punish me.

It was hard to face your Mom even one who has been around as my Mom while you are in the nude and have a penis drawn on your face in marker that has little dashes indicating cum spurting on your face. It is harder still when you realize there is still a used condom stuck to one of your boobs and your hair is all covered in semen too.

I decided to fall back on my age-old tactic of pointing out that she wanted things to be different for me than the strict upbringing she had. I told my Mom that she should just go ahead and restrict me and take away my whole Summer. I assumed she was going to do that anyway and I may as well pretend like that was what I wanted her to do in the first place.

Chapter 1 »