The Darker Years - My Sissy Story Continues

You really must read   How It Began,  Not Always Fun ,  Nothing To See Here,  My First Panties,  A Couple of Firsts,  Caught My First Bra,   My First High School Dance,  Kerri's House, Endings and Beginnings, for this post to make sense. Obviously the dialogue is not verbatim but it's as close as I can remember it. The experiences were real as were the young ladies involved. I began this blog intending to tell how I came to be the Sissy girl I am today and this is the the beginning of the next part of my story, I intend to continue to tell more of my experiences, both good and bad and I hope you, my sweet readers, will come along on the ride.

In my prior posts I have told the story of my first love and my first betrayal. I have told how I first dressed in women’s clothes, panties first then a bra then the whole thing, skirts and dresses and so on.

I have told of losing my first love but finding my second. There’s more to my story and I decided back at the beginning to tell it all. There were times that were not fun, there were times when things took a decidedly darker turn. But I’m here with you now telling the tale so I guess you realize I got through it all.

A couple of things happened in a very short time after I broke up with Gail. My fathers Great-Aunt Agnes passed away and left him her house which we were going to move into after school ended in June. Her house was in a town about 25 miles from where we were so I would be going to a new school and leaving behind everything and everyone I knew. There was no Facebook then, no Skype, if you wanted to send someone mail you had to use a stamp!

I was devastated by this news. I would be moving just far enough away from Kerri to make a relationship almost impossible. I was several years away from getting a drivers license and the only way to get back and forth would be a train ride followed by a couple of buses.

Of course she tried to make it sound alright to me, when we next got together I ended up wearing her school uniform and crying on her shoulder while she stroked my hair and reassured me that it would all be OK. We didn’t do anything sexual that day, we just spent the day together I guess like two girls would. It was very bittersweet in that I loved spending the time with her, I loved dressing in her pretty things, but I was so distraught at the prospect of losing her that the day was just full of tears and sadness for me.

 

We made a date to meet at the local Shopping Mall the following Saturday and she kissed me softly and made me promise that I wouldn’t shed any more tears, we had a few months to go yet and we would work it all out.

My older brother had been feeling ill for almost the past week and my mother had at first thought it was the flu or something like that. When he still showed no signs of regaining his strength by Friday my parents decided it was time to take him to see the family physician. They were going early Saturday morning while I stayed home until it would be time to meet Kerri at the Mall.

My mother had left me money to get something to eat and told me to call if I would be late or if I needed a ride home. As they got into the car I could see my brother was feeling ill, he was normally a very lively guy, a typical jock but now I watched them pull away in the car with my mother sitting in the back seat with him, his head on her shoulder. I can still see this image if I close my eyes now. Her worried look and his head on her shoulder, his eyes closed….

After they left I watched a little TV and then dressed to go. I wore a pretty pair of blue panties that Kerri had given me the other day. I knew she would get a kick out of that and I did too judging from my little dicks reaction. I decided I had a couple of minutes and even though I was alone in the house I still went into the bathroom and locked the door before tugging away at it until I shot my load into the waiting tissues.

Forty five minutes later I was waiting in the Mall to meet Kerri. I didn’t come here very often, usually only with my Mom to buy clothes or occasionally to shop at the record store. Yes, in those days we bought records that you played on a turntable.

I smiled when I saw her approaching me but that smile slipped when she was greeted by a small group of girls who were passing by. They all excitedly exclaimed their surprise at meeting her here and asked her if she wanted to join them. Catching my eye she told them that she was busy right now with an errand but that she would catch up with them later. The group, satisfied with her answer, moved on. She didn’t really approach me right away; she waited until the girls were a little further away before joining me. She didn’t come close enough to kiss me or make any physical contact; you didn’t have to be a genius to figure it out. She didn’t want her friends to see us together.

I knew I was no great catch as a boyfriend, I mean I was wearing panties for gods sake, but I didn’t think I was so bad that she couldn’t be seen with me. In that moment I was hurt and she saw it in my face.

“It’s not what you’re thinking you know. I like spending time with you. I like you very much but they can be nasty bitches. Two of them were at the dance where Gail told all the girls that you were a sissy boy. I didn’t want to expose you to them in a public place like this where they could make a scene and embarrass you.”

 

I was somewhat relieved by her explanation and I relaxed a bit. We headed off in the opposite direction from the one the girls had taken and she began to teach me a little about window shopping. We would stop in front of the dress stores and she would point out what she liked and asked me which I liked. She would say things like “With your coloring that dress would suit you perfectly.”

I was really starting to enjoy this when we came to a women’s shoe store and she pulled me in with her. It was a self service store with the shoes lining the shelves sorted by size. There was a myriad of colors and sizes and types and she set about trying to decide which she “needed” to buy today. I sat in wonder at all the variety, I had never really thought about it before but women had more options in every aspect of clothing than men had. They could wear any fabric, any style, any color, heels or flats, dresses or pants, nylon or cotton it was all available to them where men got nothing even close to this amount of choice.

While I had been idly daydreaming she had been piling up several pairs to try on. When she slipped off her shoe I noticed her toenails had pink nail polish that matched her fingers and I commented how pretty I thought it was. She laughed and waved her foot near my face. “Oh dear, Kaaren likes my pretty toes…maybe next time I see you I’ll teach you how to do yours and then you can have pretty toes too”

I laughed but my little dick was hard as a rock!

She tried on several pairs before deciding on a pair of low heeled loafers, for school she said. Then with a mischievous glance she said “Have you ever tried on high heels?”

Not waiting for an answer she knelt down and pulled of my shoe. She used the measuring device (what do they call those things anyway?) and went to the shelves returning with a brown pair with I guess what must have been a 3 inch heel.

“Here, quick, try these on.”

“Kerri, someone will see….”

“So what? Anyway there’s no one in this aisle now and if someone comes we’ll say it was just fooling around. Please I’d like to see what you look like in them?”

As I’ve said before I could never say no to Kerri so I removed my other shoe and slipped my foot into the first high heel I ever wore. It was a strange feeling having your foot bent like that and it was stranger still when I attempted to stand. Had she not caught me I might have fallen right over. As it was I realized with one wrong move I could hurt myself pretty badly. My center of gravity was shifted and I had to try to adjust my body to it. I felt like my ass was sticking out a bit and I had to bring my shoulders back to prevent falling forwards, it was all a bit like tightrope walking I thought.

Beside me Kerri was grinning like the cat that ate the canary.

“Those look beautiful on you Kaaren. Let’s get them and you can wear them at my house.”

“Kerri, I don’t have money for these and besides where would I hide them? I can’t just keep them in my room you know.”

“Silly Kaaren, I’ve got my Mom’s credit card and you can keep them at my house. No one will notice that one extra pair among all the other shoes in my closet.”

“Anything for you Kerri,” I said. “Thank you very much.”

She kissed me on the cheek and grabbing the two pairs of shoes we went to the cashier.

As she was ringing up the sale the lady at the counter pointed out that Kerri was buying two very different sizes.

“I know,” she said as she smiled at me, “one pair is for me and one pair is for a friend.”

The cashier did a short double take looking at me and with a shrug bagged up the shoes and we were on our way.

“Kerri, why did you say that? I think that lady knew you were talking about me…”

“So what if she does, you don’t know her do you?”

“Well no but I ….”

“Stop worrying so much….let’s go get something to eat.”

Instead of heading for the food court she guided me toward a restaurant that had real tables. Seeing my questioning look she smiled. “Food court is probably full of nasty bitches right about now”

I nodded.

“And I have a credit card remember.”

We were seated in a booth and we both ordered burgers and fries, we were teenagers after all, she slid around in the booth till she was next to me.

She smoothly slid her hand into my lap and felt my little dick poking up. She gave it a little pinch between her fingers as I tried not to show any reaction in case anyone happened to look our way.

“I thought I saw my sweet little friend poking out in your pants back at the shoe store. Did the high heels turn you on baby?”

“Yes,” I gasped as she continued touching me, “They made me feel very sexy.” I was blushing deep red from both the embarrassment of my admission and the nearness of my orgasm as she continued to feel me through my pants.

“Are you wearing panties now?” she asked me softly.

“Yes. “ I gasped in response. “The blue ones you gave me.”

“Blue is for boys Kaaren, maybe I should have gotten pink for my special girlfriend?”

“Please stop Kerri; I’m going to…you know…”

Pulling her hand back she smiled, “I wouldn’t want you to make a mess in your pretty blue panties Kaaren, maybe you should carry a spare pair in your purse….you know…just in case.”

She laughed. I laughed with her. She was so pretty and sexy as hell. And she liked me. I really couldn’t believe how lucky I was!

Soon our meal came and we dug into the burgers as only teenagers can. Finishing off the last of my fries I looked up at her smiling.

“Thanks very much for everything Kerri.”

“It’s my pleasure, baby”

The waitress brought the check and Kerri signed the charge slip, as we slipped out of the booth I started toward the door. She tapped my arm and said to wait for her outside; she was going to use the ladies room.

If I had the power to stop time this would have been the exact moment I would have used that power. I would have frozen this moment and held it in place forever. But I didn’t have the power and things happen.

I stepped out into the Mall and wandered over to the book store next door. I was looking at the bestsellers on display when I heard the voice behind me.

“Hey isn’t that the sissy faggot that Gail brought to the dance?”

“I think so….yeah it’s him.” She turned to the other three girls in their group and explained how I had been wearing a bra and panties to the dance and did anything Gail told me to do.

I have since discovered that there are few things nastier than a group of teenage girls when they’ve spotted their prey. I didn’t know which way to turn as they were suddenly all around me.

The tallest one seemed to be the pack leader; she was right in front of me with a wicked smile on her face. She already knew that I was beaten before they had even started.

“So faggot,” she sneered, “are you wearing a pretty bra today?”

“Please leave me alone, I’m not bothering you.” I pleaded weakly.

“I don’t know sissyboy; maybe you’re looking to steal our boyfriends. Is that why you wear such precious undies” She laughed. They all did.

“Please…”

“Jen is he wearing a bra?”

One of the girls, Jen I guess, ran her hand down the back of my shirt.

“No the faggot is braless today Christine.”

“Please leave me alone….please I’ll just go….” I started to walk away.

They however had other ideas. They still encircled me and the tall one, Christine, asked me what my hurry was.

“No bra faggot? I bet you’re wearing panties though.”

My blushing face was almost as much as an admission that she was right and I was so regretting my decision to put them on today.

Just then I saw Kerri come out the restaurant door. I felt a momentary relief. She would help me. She’d make them stop.

One of the girls also spotted her and called her to join the pack.

“Hey Kerri, look what we found, remember Gail’s Sissyboy faggot that she brought to the dance?”

Kerri looked at me and then said to the girl, “Yeah I remember.”

That was all, no more. “We were just going to make him show us if he’s wearing panties, what do you think?” I expected her to say, “No, you bitches let my friend go.” But instead I heard “How are you going to do that?”

“Pull his pants down.” Said one.

“Make him pull his pants down.” Said another.

“I want to see.” Said a third

“Me too.” Said the other, Jen.

Kerri avoided my eyes as she said “Maybe if he just opens them enough for us to see.”

“Okay sissyboy, open those pants up and let us see if you’re wearing pretty panties today.”

I was defiant but outnumbered, “No I won’t.”

They kind of grabbed me as a group; there were a lot of hands on me all at once. I struggled but it was a waste of time, for every hand I pushed away there was another one to take its place. I was pushed off to the side away from the storefront and I felt hands, Christine’s it turns out unbuckling my belt. With an evil grin she unbuttoned my pants.

“Ready girls? Here goes…”

As she pulled down my zipper her hand brushed my little dick which was as hard as ever. Her glance at me showed momentary confusion before returning to the look of a predator about to slaughter its prey. I felt another girls hand grab my belt loops in the back and in a moment my pants were down at my ankles. My pretty blue panties with the big satin bow that I liked so much were now on view to anyone who cared to look my way. They all took a step back as if in unison to get a look at this weakling they had mastered. I had tears streaming down my face as I bent to pick up my pants. Without stopping to even fasten them I ran from the laughing girls, I noticed a couple of others, guys and girls who had stopped to watch my humiliation. I ran as fast as I could. I was afraid they were chasing me. I exited the Mall and just ran for a while, till I had to stop and breathe. Why had they done this to me, why had Kerri let them do this to me? Where was I? I realized that I had run the wrong way and would have to backtrack to get to the bus to go home.

It was while I was sitting at the bus stop that a car cruised by. “Nice panties Sissyboy!” they shouted. Kerri was in the back seat. She wasn’t looking at me. She was laughing with the rest of them.

My parents still weren’t home when I got there. I went to my room and tore off my pants, pulling the panties off with them. I tore them into pieces and after putting on sensible boys underwear dressed and took the fragments of nylon and ribbon and buried them in the trash can outside.

The phone was ringing when I got back in; I picked it up and said “Hello.”

“Hi it’s me…” It was her, Kerri, another girl that I trusted, another that turned on me.

I slammed the phone down.

In seconds it was ringing again.

I picked it up, “Please” she said “Let me explain.” She sounded like she was crying.

I said nothing.

“Are you there, please talk to me, I’m so sorry, I just want to talk to you, please answer me…”

I said nothing.

“I know you’re there I can hear you breathing. I couldn’t stop them, you have to know that. There wasn’t anything I could do. I couldn’t fight five girls. They’re mean bitches and that Christine is the meanest queen bitch of them all. She would have made my life hell for the rest of high school. I know you’re hurt, but you’re moving away soon…you’ll be out of their reach; I’d have to live with them every day. I know I sound weak and awful but it’s the truth. I was afraid of them too…are you listening? Please say something, anything?”

“What do you want me to say?” I was angry, confused, humiliated. “I thought I meant something to you. I thought we could be together. I guess I was wrong. I guess I’m just a dress-up doll for you to play with in private. I guess you’re too embarrassed by the Sissyboy Faggot to be seen with me.”

There was silence on her end; I thought I heard her crying.

“It’s not fair,” she finally spoke, “I didn’t want any of this to happen, it wasn’t my fault, but don’t you understand I’m afraid of them, they hurt you today, they can hurt me every day for the next couple of years….you’ll be leaving soon….please I don’t want you to hate me, I was just afraid….I’m sorry…”

She was crying, so was I. “You hurt me so much Kerri, I have to think about this for a couple of days. I’ll call you later this week.”

I didn’t wait for her to reply, I couldn’t hear anything else right now. I hung up the phone.

Several hours later I heard my fathers’ car pull into the driveway. I stayed in my room nursing my hurt feelings and trying to figure out what I was doing and what I was going to do.

My mother came to my door and after tapping lightly she came in and sat next to me on the bed. She had something to tell me and she wanted me to listen very carefully. She told me that the doctors had diagnosed my brother with leukemia and that his prognosis wasn’t good. She had tears coming as she told me this and when she finished she put her head in her hands and wept. I held her there for a while and as she quieted I asked her if she needed anything. She asked me to get her a glass of water.

 

As I entered the kitchen I found my father there drinking vodka straight from the bottle. He was staring at me as I told him that Mom wanted a glass of water. He took a long swig and looked me right in the eyes and said “Why couldn’t it have been you?”

 I have been haunted by those words for many years.

The weeks came and went in a blur after that between school, preparing to move, and awkward trips to the hospital to see my brother. Although we didn’t get along he was still my brother and this disease was robbing him of his life and I felt pity and sorrow and dozens of other emotions as I watched him fade away.

As for Kerri, word gets around pretty quick and she called to offer me any help I might need during my brothers illness and I basically shut her out. I could not allow myself to be hurt more right now. I was hurt already in so many ways. Eventually her calls stopped.

Just before school ended in June my brother passed away. There was a large turnout for his funeral, it seemed like the entire town was there. I saw Kerri coming toward me and as she reached to give me a hug I stepped back and said what I have come to believe is the single stupidest thing I had ever, or perhaps will ever, say.

I told this beautiful, caring, funny, smart girl to “Leave me alone!”

How often over the next few years did I wish I hadn’t done that? The look on her face was as if I had just hauled off and smacked her. She looked at me sadly, nodded and turned and walked away.

Several weeks later we moved into the new house. My room was bigger and had a great big closet. One of the first things I moved into that closet was the box with my small collection of women’s clothes.

My parents were grieving and they had each other to hold on to. I was pretty much left to myself. I had been cut off from everyone I knew; I had loved and lost 2 girls in my life. I had a new school to get used to. A strange new neighborhood where I knew absolutely no one. I was confused about so many things and I had no one to talk to anymore!

I really felt completely alone in the world.