My First Time ( Mac & I. )

I had been emailing Mac for about 3 months about wanting my secret desire to be treated like a sissy with a man. Today he was going to pick me at noon. I didn’t sleep the entire night nervous if i would go through with meeting him. Part of me was scared that he might be a killer while another part of me was fearful he might just hurt me. He seemed like a nice older man and said he had always been attracted to men. I didn’t want to be with a man only because they couldn’t get pussy.

I emailed Mac at first and told him many many times I was very shy but the more we emailed the more i opened up to him about the really nasty things I wanted a man to do to me. He said everything that I emailed him made him super horny. We spent hours every week emailing so part of me felt that I could not stand him up while part of me really really wanted to meet him. I emailed him telling him the dick picture he emailed me made me drool when i looked at it.

( Below is the real first picture Mac sent me of his huge dick.)

My First Time ( Mac & I. )

Mac emailed me while I was in my bathroom getting ready for our date asking if we where still on for noon. I texted him my address and told him to text me when he was out front. God I was so nervous and felt like i might get sick. I should cancel I thought but as I stood there in my black thigh highs, black panties and black bra the sissy part of me texted Mac back that i can’t wait and that he could do anything he wanted to me smiley face. Well there it was i thought and Mac replied a few minutes later that he was out front. I started shaking and emailed him back that i would be out in five minutes. Oh my god was I going to do this? What would it feel like to have his big cock in my mouth?

I put on my grey baggy sweat pants and sweat shirt then my shoes stood there for a moment peeking out the shade of my front window looking at Mac in his truck. What was I doing? Why did i give him my address? I didn’t think but grabbed my keys putting them in my bag slung it over my shoulder and as i was walking down my driveway towards Mac’s truck I just kept thinking What was I doing? I was going to get fucked.

I walked up to the passenger side of his truck and opened the door and Mac looked at me and asked “Sweetie?,” which looking down I responded in a soft voice “Mac?.” He said well hop in the passenger seat and I remember thinking well it’s good he didn’t reject me. Part of me was scared of that also I guess.

We drove a few blocks before either of us spoke and Mac asked if I wanted to go out to eat first and I said no. He then asked me What we last emailed about? And i could say nothing but shook my head up and down. We drove out of town about 20 minutes to the middle of nowhere when Mac pulled down a dirt road. About 10 minutes down the dirt road Mac stopped the truck and said we where here, I said nothing and got out.

Mac rummaged around his truck slung kind of a back pack over his shoulder and looked at me and said ready? I just nodded my head yes and followed him as he walked away down a sort of dirt path way. I kept thinking as i walked behind him for about five minutes of how scared i was and how i was going to make the first move.

Finally in a cracked voice barely above a whisper I asked if Mac had brought the stuff we had emailed about in the pack. He stopped walking and said yes while smiling at me. I didn’t even think as i said can I see your handcuffs.
Mac unslung his pack saying a very jolly okay and got on one knee and was going through his pack. Again without thinking i took my shoes off let my sweat pants fall off me and then took off my sweat shirt top. As i was putting my shoes back on Mac look up and said wow i was sexy all dressed up. I said a small thank you and as i was positioning my back to him Mac reached out to me holding the handcuffs. I kinda smiled at him as I took them from him.
I hesitated for a second than tightly handcuffed both my wrists in front of me. A second later Mac was behind putting a soft super white blindfold over my eyes as my body shuttered. Oh my God i can’t do this I thought to myself.

Mac had me by the chain of my handcuffs and lightly tugged me along. We walked awhile I was scared while every now and then a slight breeze made me violently shake as it hit my sweaty skin. We walked on and on and on it seemed I couldn’t but help to think what this must look like to someone else. With every step i felt so submissive every now and then a plant hit one of my legs god I couldn’t believe I was letting him do this to me. I kept opening my mouth and kept trying to keep it closed. I didn’t want Mac to know I really wanted to try sucking dick and my mouth kept telling on me.

Mac said for me to stop and I did. He told me to get on my knee’s and I just stood there kind of stuck in fear wanting to run away when Mac said for me to get on my knee’s a little louder and I felt his hand on my shoulder. I got on my knees for him and felt something silk like also around my wrists. Then a hand was kind of lifting up one of my ankles then my shoe was off. Then my other shoe.

I just stayed there ever so still my body shaking and my heart pounding on my knee’s when i felt just the tip of Mac’s dick on my bottom lip. I quickly snapped my head from his dick to the side Mac said nothing while my mouth seemed to be filling with a huge amount of spit. Mac’s hand was on my cheek and I smiled and again I felt him on my lip.

This time I thought to myself he is going to force me to do this so I might as well control how much dick I suck if I didn’t like it then I could stop and I leaned my head a little forward and took maybe just the very tip of Mac’s dick in my mouth and sucked it a little.

I remember thinking this wouldn’t satisfy him for long so i flicked my tongue back and fourth every now and then.
At some point I took Mac’s whole head in my wet mouth and just a little of his shaft and Mac moaned.
I like him in my mouth and decided to maybe choke on him a little as I was sliding my mouth up and down on his dick I decided to see how much of him i could swallow.
I wanted to please him and show off how much of him I could take in my mouth and as my head bobbed up and down on him I thought here goes and slowly slid him more and more and more in my mouth and he hit the back of my throat and i gagged, my stomach heaved and Mac was out of my mouth.
I was struggling for air and spit drooled from my bottom lip down my chin and I remember thinking how sexy I felt in my thigh highs kneeling in the warm sand when my spittle landed on my chest. Just as I got my breathing back Mac asked if I was okay. I responded by lifting my head up opening my mouth and licked my lips.

( Below is a real picture Mac took while in my mouth.)

My First Time ( Mac & I. ) 2

Mac was then back in my mouth with just his tip and I wanted to thank him thinking what a nice man for letting me do this at my pace. I took some of his shaft in my mouth again sliding back and fourth. At some point Mac was facefucking me and I tried to take him in my throat more than one time. One time while Mac was in my throat I began to gag hard and he just held it there. Then he slid out of my mouth and saliva was all over me. When Mac entered my mouth again he did the same thing over and over again I was getting so weak. God I liked this so much. Everytime I gagged he held it awhile and then would let me catch my breath. More than once I tried to moan no and I tried to lean back away from him but he held me in place.

Mac was facefucking me gagging me harder and harder I lost control of him I struggled even trying to get up. I felt spit oozing out of me, my eyes where full of tears but i knew he wasn’t going to stop. No matter what I did he continued to facefuck me until i felt like the shaft of his dick swell like a fucked up marshmallow and he exploded in my mouth and throat. He thrusted like 4 or 6 times my mouth full of cum. I was choking on his dick and didn’t like his salty hot cum when Mac finally pulled out of me i hung my head in shame wondering if he noticed that I spit out slowly some of the left over cum that was in my mouth down my chin. Mac then asked me when it sounded like he caught his breath how I liked it and what surprised me most in almost a soft woman’s voice before I could think of what I had even said i blurted out “I love you.” Mac chuckled a little and said stand up as he kind of roughly pulled me up with his hands underneath both of my shaved arm pits.

I didn’t know what Mac had planned next and he walked me somewhere just a few feet and I just stood there thinking what a whore I was when my hands seemed to be being pulled by something above. The next thing i knew my hands where pulled up above my head and I was standing on my tippy toes.
I just stood there. Mac then asked if i was comfortable and i said a soft Mhmmm. He then told me he was setting up his camcorder before he whipped me so my ass was loose. I said nothing. Every now and then while Mac was doing what he was setting up he would grab me by the chin and sometimes lightly kiss me other times he would kiss me really rough while squeezing my ass cheeks really hard. Finally Mac asked if I was ready and as he was pulling my black panties off and I said nothing until the first time his paddle hit my oiled bare ass and I screamed……………..

( Below is just one of the many pictures Mac took of me before he broke me. )

My First Time ( Mac & I. ) 3

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