HaileyRose
Male
*Note. These are real experiences as i remember them, memories written in a story format. Im sorry for the lengthyness*
I was asked the other day how i got into all of this, at the time i didnt quite remember, And so, i pondered on this. What was the single event that thrusted me into being feminine, wanting to be a woman. To serve real men and most of all. Why? ..
So. In light of this. I will be posting a series of threads to share with you guys the experiences of my journey to becoming a true sissy.
I wasnt always girly. Matter of fact. I was quite manly. (Or so i thought hehe) I boxed. I played football. I liked video games, i drank beer and up until this point i enjoyed plenty of women and the love making/general sex that came with them. however as i am writing this ive been girly for so long i dont remember the feeling of masculinity. So i had to retrace my first experiences.
Que my last and final girlfriend. Holly.
She was so beautiful. Long blonde hair, perky breasts and slender fit body. She was tiny. Her ass was a perfect heart. She was quite beautiful and honestly i loved her, Alot. I still do. And we're still friends that meet up regularly.
. Anyway anyway! I Digress.
Holly was among many things, Stranger than fiction.
Most of all her sexual interests. Around our second year being together the story started to unfold.
"Honey. I want to try something new in the bedroom." She said laying her head in my lap as she looked up to me. "Uh..like what though..im not like gonna do anything weird" she nodded in understanding. "Nothing weird. But maybe painful for you. At first anyway. I want you to watch me get fucked by a black guy" now what the actual fuck? I thought to myself. Is she serious? I was shocked but really i couldnt be mad. She did let me have a threesome with her bestfriend on my birthday. So its not like i can disagree. "Well..i guess alright. You gave me that present with you and amelia. And i love you so its only fair?"
"Yes, exactly. Thats why i love you"
"I love you too Holly." We kissed we hugged and she put her arms around my neck. "Listen. You can only watch though, okay? Be a good boy and no touching"
"Alright." I said not even thinking about it.
What have i gotten myself into i thought.
That night. The doorbell rang. Holly was done up in sexy black lingerie. "Hey daddy!" She pronounced. What the fuck? She never calls me daddy. She doesnt even call her dad, daddy. a tall handsome black man entered our home. "Hey whats up man my name is Darren." I shook his hand. "Hey." I said. Feeling an array of emotions i couldnt really explain. Anger, jealousy, Sadness. Resentment and regret. But it was too late. We were doing this. "You're actually kinda cute man."
"Im not bisexual. Im just here to watch"
"Oh okay i got you" he chuckled after his response. I sat in the chair. Holly was in the kitchen. Looking at me with..i dont know how to describe her eyes. I think. now that i think about it i think it was her plan all along. and the look in her eye was something sort of "this was my plan unfolding perfectly"
As Darren was Fondling himself through his sweats. she walked over slowly. Kneeling infront of him. she pulled out his waistband.
Releasing what i can only image was 8 or 9 thick inches of chocolate. It bounced and slapped her in the face. She giggled. "Fuck its so big. Look at this thing baby." She grasped it and looked over to me. "Its so much bigger than yours." Those sentences made me squirm in my jeans, There was a sensation in my stomach and chest. I watched as she sucked. She was really enjoying herself. more than she seemed to ever enjoy us. Why was she with me then?
What was her end game?
My dick instantly sprang up when he finally put his inside of her. The look on her face ill never forget. Her eyes shot open her mouth gaped wide "OoooooohhhhhMYGOOOOODDDDD" She screamed as this stalion pushed deeper inside of her. He fucked her for what seemed like hours and in the end. I couldnt help but pull my pants down and begin rubbing myself. I came. She came. He came. The deed was done. Darren left. Me and Holly took a shower. I felt so many things i didnt know where to start. I was washing myself down with water. She came up behind me grabbing my dick. Stroking it gently. "You enjoyed yourself" i couldnt deny that i liked it. But it still hurt. My girlfriend of 2 years just had sex with another man in front of me. I said nothing.
"You dont have to say anything. I saw you cum and when you did i did too. I love you and love and sex are two different things. And just to reinforce you. I do orgasm when we have sex. You and I make love. And thats an entirely different feeling than this type of sex. If you want to leave. I'll understand."
I was silent for a moment i had to think about it. She did introduce me to a lot. And i did love her more than anything and cmon. I did cum. A lot. "No youre right. It was hot. I want to do it again." She smiled like the devil after signing over your soul. "I'll set one up tomorrow."
More next time
