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, for this post to make sense. This is the tale of my very first sissy experience and for good or ill it was the beginning of my sissy life. 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 final chapter of the beginning, 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.
A week or two went by since my delightful day with Kerri. I was reliving my experiences with her on an almost hourly basis. My tiny little dick was actually kind of sore from all my frantic tugging at it but, oh how I wished she would call and we could play those sexy games together again.
A week or two went by since my delightful day with Kerri. I was reliving my experiences with her on an almost hourly basis. My tiny little dick was actually kind of sore from all my frantic tugging at it but, oh how I wished she would call and we could play those sexy games together again.
I could still picture her naked body; her tits and pussy were burned into my mind. The taste of her was unforgettable and I yearned to get down on my knees and use my tongue on her to make her cum again.
I was a little confused about wearing her clothes and how it made me feel, I mean I was a boy and I shouldn’t be wearing panties and bras. But I loved it. I loved the feel of the bra wrapped around my chest, the gentle tug of the straps on my shoulders. I loved the soft and sexy panties, cut so much smaller than my briefs and in soft cotton or nylon that gently cupped my little dick making me hard almost constantly.
When she had me wear the skirt and blouse I felt so different, as though I was a different person. I was me, but I was a feminine me, and to tell the truth, a happier me.
So it was with great anticipation that I ran for the phone when my mother called to tell me it was for me.
It wasn’t Kerri, it was Gail.
“Hello Sissy, have you missed me?”
I tried to hide the disappointment in my voice.
“Oh, hi….um yeah sure I’ve missed you. What’s up?”
“What’s up Sissy? Well my friend Kerri says that you and her had a nice talk at the dance while she gave you a tour of the school and so I offered to let her come over and we could have some fun. Be at my house at 11 on Saturday morning, don’t be late Sissy or you might get a spanking.”
My mind was racing; obviously Kerri hadn’t told Gail what had happened between us at the dance or at her house. But what could she be thinking? What was going on?
“Yeah I can do that,” I said, “11 on Saturday…sure no problem…”
“And remember to wear my bra and panties Sissy.”
“C’mon Gail please, I don’t want to do any of that stuff.” I don’t think I sounded convincing, I wasn’t that good an actor.”
“You just be here and be dressed or I could always give your Mom and Dad the lovely photo of you, you look so pretty in it. I’m looking at it right now.”
“OK Gail you know I’ll be there.”
“Great so we’ll see you then Sissy. Bye bye.”
It was hard to reconcile this girl I had grown up with as being my tormenter. I had always thought that we were friends. I had once thought we were more than friends, she had always been the boss in our relationship but now she was turning mean.
I was idly thinking about what might happen at Gail’s house and of course considering another trip to the bathroom to relieve my hard little dick when my mother shouted that there was another phone call for me.
I was very relieved when I heard Kerri say “Hello….Kaaren. How you doing honey?”
“OK I guess,” I answered a little shakily, “I got a call from Gail and….”
“Oh good, you didn’t let on about us hanging out together did you?
“No, I can’t afford to piss her off remember I told you she has that picture of me…”
“I know and that’s what we’re going to take care of on Saturday. When you get there she will probably try to embarrass you in front of me or make you do things to her, or me for that matter. I want you to just go along with it. Try to have fun like we did the other day at my house. At some point I’m going to get her to show me that picture and you can bet when we leave there that that picture will be in my pocket.”
“Wow that would be great, but there’s nothing stopping her from just telling my folks about the…um…underwear and stuff and then I’m just as dead either way.”
“I thought about that and I think you should just deny everything. You could call me and I would back you up, you know, tell your Mom and Dad that we’re together and Gail’s just being jealous and trying to hurt you.”
“I guess that might work, but how are we going to get the picture?”
“It’ll be like Mission Impossible on TV, we’ll play along and when she doesn’t expect it. pow, we got her.” She laughed, it was a wonderful sound.
I was beginning to like the idea, if I could get rid of the picture I figured I could walk away from Gail and into Kerri’s arms.
“Okay, I’m willing to try it, but she already told me to wear her underwear so I guess we’re not going to just talk.”
“Oh sexy Kaaren, what could she do that you haven’t already done with me? If you pretend it’s just us you might actually enjoy it.”
“I doubt it but I’ll try, thanks for trying to help me Kerri, you’re really great.”
“Okay Kaaren, I look forward to seeing you on Saturday. Bye.”
As we hung up a shiver of anticipation went through me and it was off to the bathroom again. Pulling on my little dick I was remembering Kerri’s naked body and thanking my lucky stars that she seemed to really like me.
The days passed and on Saturday morning I slipped into the bathroom and put on the bra and panties under my clothes, I wore looser clothes and hoped they concealed my secret from other eyes. I ran past my Mom and said I would be out with a friend from school and would be home later. I didn’t stop because if my Mom gave me a hug the secret would be out.
“OK,” she called after me, “supper’s at six so be home by then.”
“OK” I replied as the door was swinging shut behind me.
As I rode my bike toward Gail’s house my mind was racing, full of dread and full of excitement. I wondered what was going to happen and what new torments she had in mind. I was looking forward to seeing Kerri again and my little dick was rock hard in the soft yellow panties as I pedaled the few blocks.
When I arrived I put my bike in the driveway and saw a girls bike there that I figured must belong to Kerri. I turned and climbed the steps rang the doorbell, my hand shaking as I did.
Gail opened the door and I could see Kerri standing in the hall behind her. Gail had a big grin on her face.
“Hello Sissy,” she practically shouted the word. “Are you dressed like I told you to?”
So this was the way it was going to be, no build up just going for it right at the start.
“Yes Gail, you know I am.”
She grinned at me and I saw Kerri roll her eyes behind her.
“Show me,” she said, “take that shirt off and let me see the Sissy in his pretty bra. In my pretty bra I should say.”
I turned to close the door behind me but she stopped me.
“I didn’t say anything about closing the door; give me your shirt right now.”
Again you have to remember that I’m naturally submissive by nature and I had already experienced enough to know that she wouldn’t change her mind. She enjoyed humiliating me and in my deepest heart I enjoyed it too!
“Please Gail, someone might see me. Please let me close the door…”
Kerri started to say something but Gail told her to wait.
I slowly unbuttoned the shirt and slipped it off feeling exposed to the world as the soft breeze blew against my skin. The yellow bra seemed even brighter in the sunlight and I was terrified that anyone passing could see me.
“Very good Sissy now give me your pants.”
“Please just let me close the door, I’ll do anything you want…”
“Oh I know you’ll do anything I want already. You’re a wimpy little sissy who let’s girls push him around. Now do as I say or I’ll put you out on the front steps and make you do it out there!”
Over her shoulder I saw Kerri licking her lips and her hand was slowly moving over her breast. I almost came on the spot and I realized it wasn’t going to take very much more to make me cum in my panties.
I knew Gail didn’t bluff so I quickly kicked off my sneakers and taking a deep breath pulled down my pants revealing my pantied bottom to the outside world while the two girls got to see my little dick making the panties stick out and a little wet spot where I had dripped a bit of pre-cum.
Gail pointed at the spot and laughed, “Look Kerri, the poor little sissy is dripping in his pretty panties!”
Kerri stepped up behind Gail and although she was giving me a hungry look she said, “C’mon Gail, let’s take him inside. Close the door. What if one of your Mom’s friends goes by and sees him there like that?”
“Oh all right, I guess you’re right. One of those old neighbors might see him and have a heart attack.”
She pushed the door shut and turned to the stairs, as she had her back to us for a moment Kerri blew a kiss at me as I silently mouthed a “Thank you” to her. We followed Gail up the stairs, me behind her and Kerri behind me. I was painfully aware that she was at eye level with my pantied ass and I found that incredibly embarrassing even though she had seen just about every inch of me the last time we were together.
We entered Gail’s room and she and Kerri sat together on the bed leaving me standing, red-faced, facing them.
Kerri turned to Gail and asked, “Didn’t you two kind of grow up together, why are you being like this with him?”
“Yeah my Mom wanted me to marry him since we were babies. Ha, if she could see him now! Who would want a pathetic Sissy like that?”
Kerri looked at me, “So why do you do this for her? Do you like wearing girls stuff? Do you like when she picks on you? From the look of your panties you seem to be enjoying yourself.”
She was very good at pretending that she didn’t know all about me.
“She makes me do it,” I replied, “It doesn’t matter what I like. If I don’t do what she says she’ll show something to my parents and I’m afraid they’ll throw me out or beat me.”
She turned back to Gail, “You’re forcing him to do this, that’s kind of mean don’t you think. What do you have to show his parents?”
Gail was getting annoyed. This was not going the way she wanted. She walked over to me and slapped me, hard, the sound making Kerri jump and gasp. Tears immediately came to my eyes as my hands came up to protect my face.
“Tell her the story Sissyboy. Tell her how this started. Tell her what you did. Tell her what you stole.”
She slipped behind me and began slapping my ass, softly at first.
“I stole these panties from her drawer,” I explained, “ I don’t know why I did it but she knew I did it and to punish me she made me wear this bra and she took my picture in it and that’s what she has to show my parents. That’s why I have to do what she says.”
She slapped my ass hard enough to make me jump.
Kerri looked at Gail as she spanked my ass. She came over and traced a finger around the bra cups.
“What about the other stuff you told us Gail, you know about, you know, making him, um, you know how you used his face to cum. Can we do that?”
With a final resounding slap she stopped hitting me thank god; my ass felt like it was on fire. She smiled at Kerri and told me to lie on the floor. Gail was wearing a skirt and she stepped up and lowered herself onto my face, settling her soaking wet panties against my mouth and nose. She slowly began to grind against me as her breathing started to get heavier.
“Where’s this picture Gail,” asked Kerri, “I’d like to see it while I wait for my turn to ride.”
Gail laughed and pointed to the bookshelf. “I keep it in my copy of Alice in Wonderland.”
She was breathing really heavy now as her juices began to seep out of her panties onto my chin and lips.
I couldn’t see her but I heard Kerri moving around me. Oh my God, this was going to work! Kerri would get the picture and I can tell Gail to fuck off the next time she calls. She was groaning a little now and her body was starting to shudder and I figured she must be cumming soon. My little dick had pre-cum pretty much streaming now. One touch and I would explode. She was really grinding on my face now and it was actually a little scary because she was hurting me and she was cutting off my air for a little time. Finally as she moaned “Oh God,” she flooded my face with her juices as she came. She rubbed herself for a little while against my chin and I think she had another orgasm before she finally stopped.
As she caught her breath she looked at Kerri who was standing, staring slack-jawed at what she had just seen.
“That’s about all a sissy like him is good for, you want to try Kerri. You should have worn a skirt, I guess you can ride him with your pants on but that won’t be as much fun.”
Kerri looked at her and laughed, “I have a better idea than that.” She said as she opened her pants and began pulling them off.
Gail seemed actually surprised, “Kerri, you’re going to let him see you with no pants on! That’s so crazy. Are you sure? He’ll see almost everything.”
Kerri sat on the edge of the bed in her pretty white panties and told me to come to her on my hands and knees. She grabbed my hair and pushed my head between her legs. Gail was shocked when Kerri pulled her panties aside and pushed my face into her soaking wet pussy!
“Kerri! You’re letting him see you. Oh my god aren’t you embarrassed.”
Kerri was too busy to reply, she was pushing my head into her delicious crotch and I slipped my tongue out to taste her. I loved the taste of her and I knew she was going to cum very quickly. Then I felt the strangest thing. Her foot was near my hard little dripping dick and she started rubbing it with her toes. I began to spurt almost instantly and as I was cumming into my panties she came on my tongue. She pushed me away and lay back on the bed breathing hard. Gail seemed mesmerized by Kerri’s beautiful little pussy, bare and glistening with her juices and my saliva. Kerri was lying back with her eyes closed as I watched Gail lean close and reach a very tentative finger to touch her. Kerri purred as Gail’s finger made contact with her and slid between her glistening lips.
“Mmmm, enough sissy,” she groaned, she thought it was me!
Her eyes opened and she jumped back, “Hey HEY, what the fuck are you doing. Gail you lezzy what the fuck do you think you’re doing???”
Kerri scrambled around her reaching for her pants as I knelt there amazed at what had just happened.
Gail was babbling at her as Kerri pulled her pants on, “I’m sorry, I didn’t mean anything I don’t know why…”
Kerri looked at me and told me to get dressed, and then she looked at Gail and practically spat out her words, “You know a lot of us thought you might be some kind of lezzy but now I know for sure. Once I tell, your life in school is over.”
This was back then, things are different now, but back then what Kerri said was true. We all knew it. Gail was starting to cry. The power in the room had all shifted and now it was Kerri in control, I was pulling my shirt on as I watched them.
“Please Kerri, please don’t tell, please don’t do that to me…I didn’t mean to do it…I don’t know why I did it…please…please…” she was sobbing now.
Kerri looked down at her where she sat on the bed crying, “You’re saying the same thing he did when you caught him with your underwear but you put him through hell. You publicly embarrassed him and you used and abused him…well the shoes on the other foot now. I’m leaving and he’s coming with me. From now on you leave this boy alone, you want me to keep quiet, that’s the price. Oh and I’m taking that damn photo with me too.”
Gail had her head in her hands, crying and nodding, “Okay okay, if you want to take it then take it. Just please don’t tell.”
Kerri grabbed my arm and we walked to the door, as we left I could still hear Gail crying and despite all she had done to me I felt bad for her. We didn’t speak as we got on our bikes. We rode a block or two before we came to the road where we had to split up to go to our homes. Kerri smiled at me.
“I guess that all worked out OK then, we got the picture and we got Gail to agree to leave you alone too.”
“I know I shouldn’t but I feel kinda bad for her, she’s really upset and scared.”
“She’s tough she’ll be fine and just between us,” Kerri leaned in to whisper, “her finger felt fantastic!”
She laughed at the look on my face. Reaching in to her back pocket she handed me the wrinkled photograph and leaned over and kissed my cheek.
“If I was you I’d get some new underwear Kaaren. I’ll call you soon.”
She turned and pedaled away. I watched her go for a while before turning toward home. A chapter in my life had just ended, with a surprise ending, and hopefully a new chapter was beginning with a girl who actually liked me for whom and what I was.
I saw Gail now and again through the years since that afternoon, she had been very unhappy as a teenager and part of that seems to have come from her refusal to admit to herself or anyone else that she was gay. Being gay was tough years ago and it made her life harder than it should have been. We bumped into each other on the street not that long ago and we went for coffee. She told me how sorry she was for the way she had treated me back then and I told her she could make it up to me by paying for the coffee. We had a lovely chat and reminisced about old times and old friends and when it was time to part she hugged me and ran her hand over the bra strap she could feel under my coat. She laughed and smiled and I believe we parted as friends.
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