Sissy Exploration Pt. 01

I started off the way many sissies do, looking at sissy sites on the internet then I started buying bras and panties online from Victoria's Secret to wear. At first it was just to wear while I was looking at porn and playing with what I now call my clitty. However, soon I started wearing a bra and panties to bed at night because I loved the feeling of waking up in the morning dressed as a sissy. I then started wearing panties under my jeans when I went out of my house and a few times I got really brave and wore a sports bra too. I started camming as a sissy which was a huge turn on to me. I loved stripping and doing whatever someone on cam told me to do, knowing that I was making men hard (and cum)! After a while, I wanted more so I started looking on Craigslist to see who was around. Eventually, I worked up the nerve to post this:

Sissy looking for couple. I want to learn how to suck cock and I am looking for a woman to guide me. I am willing to orally service both partners.

I was shocked when I received a reply within 6 hours of posting. A woman said she and her husband had seen my post and they were interested in discussing further. After exchanging a few emails we agreed I would meet them at their house where I could meet them and she could teach me how to service a cock properly. She said that if things went well fun things could be in store for everyone.

So, that Friday night I shaved myself smooth, painted my toe and fingernails a pretty bright pink color, put on a cute purple matching bra and thong set, a thin light pink spaghetti strap cami top, tight black leggings, and a pair of black flats. I was so nervous that when I walked up to the front door I was shaking. I almost turned back but I hurriedly pushed the doorbell before I could decide to chicken out.

The door opened and a stunning brunette woman in a tight fitting strappy black dress and sliver high heels opened the door and said "Welcome, come inside!"

She brought me into the house and closed the door. "My name is Rachel, and my husband is Mark, he will be home soon. Let's get you all fixed up and ready for this evening."

She took me back to the bedroom and applied makeup and made sure I looked my best to meet her husband. As she worked, she told me what to expect when Mark came home. "He will check you out before he lets you near his cock. Submit to him and let him touch you anywhere he wants. Make sure you work on making his cock hard while he does this and if you do a good job he will let you suck it." I nodded, not trusting myself to speak. She then took off her dress revealing a black bra and matching black thong. "There, I am wearing less than you now, does that help? I will be with you the whole time to guide you in pleasuring cock." She then came close to me and ran her hand along my crotch, feeling my semi-aroused clit. She kissed me slowly then whispered, "Your clitty does not lie, you are loving this sissy. Soon you will be a good cum whore."

I then heard the front door open and Rachel walked out of the room to get him. Moments later she returned with her husband. "Dear, this is the sissy we found, does she meet your approval?" Mark walked around me, looking me up and down. Then then started to fondle my bra through my top. My nipples burned from the stimulation and suddenly he jerked my top down, exposing my bra.

"Nice bra sissy" he said. He walked around behind me and started to caress my ass. Then he suddenly smacked my ass so hard I let out a small gasp. "Cute ass, maybe one day I will fuck it. Would you like that sissy?" As he said it he grabbed my throat from behind and started to gently choke me. As he stood near me I could feel his manhood pushing against my ass and I felt it was growing. I remembered what I was supposed to do and reached behind me and started to stoke his cock through his pants. "Good sissy," he said, "would you like some cock?"

"Yes Sir, please." I whispered.

"First I want to see if you matched you panties to your bra like my wife," he said. With that he quickly hooked his thumbs into my waist band and roughly jerked my leggings to my knees. He smiled and said, "Very good for a first date sissy. You may suck my cock now."

Right before I sank to my knees in front of him, Rachel said, "I want you to suck his cock for me. I want to hear you choke on it and I want to see your face painted with his cum."

"Yes Mistress." I said as I got on my knees and he unzipped his pants and pulled out his semi-hard cock right in front of me.

As I stared at his semi-hard cock Rachel kneeled next to me and said "Give it a kiss, show him you want it." I started kissing his cock, then licked it. All along the shaft, from his smoothly shaven balls to the tip, nice and slow. I felt it grow as I got closer to the tip. Next I gently took the head in my mouth and sucked on it while swirling my tongue along the most sensitive parts of his cock. When I licked the tip again I tasted a little precum. Clearly all the studying I had done on porn sites and reading Cosmo magazine articles was working. Next I started to slowly take more of his cock into my mouth. He was completely hard now and his cock was a little bigger than the largest dildo that I had practiced on. I went down on his shaft as far as I could then stopped there. I went up and down a few times to loosen my throat then I took as much of him in my mouth as I could and held it until I almost gagged.

Rachel noticed because the next time I went down she held my head and pushed me until I took more of his cock in until I choked. "Good sissy," she said as she let me up "Choke on his cock, make it nice and sloppy." Up to this point I had taken all but about of an inch of him in and I knew she was going to make me take him all the way in. Rachel grabbed my hair and pushed me down on his cock until I choked again but this time she did not let up. She slowly pushed harder until I had taken all of Mark in. I choked a couple of times on the way down and I could feel tears starting to run down my face. "Honey, do you want to take over?"

"Sure, I would love to make her choke on my cock." Mark said as he grabbed my head and proceed to shove my head down on his cock as he thrust into my throat.

As he was thrusting Rachel said "Look up at him so he knows you appreciate this sissy." I looked up at Mark and I could tell he was really enjoying it. My gag reflex was a bit more under control now so his thrusting grew faster and harder. Spit was running down my chin and between the cups of my bra.

All of a sudden Mark pulled out of my mouth and started jerking off. "Open your mouth sissy," he said. I did as I was told and soon a rope of cum splashed me in the face. More cum followed, splashing me in the face, in my mouth, and in my hair.

When his cock was done erupting Rachel said "Swallow it sissy then clean his cock off." I closed my mouth and swallowed, feeling the salty, warm cum slide down my throat and into my stomach. I took Mark's cock in my mouth and gently sucked off all the remaining cum that did not make it onto my face. "So how was she honey?" Rachel asked.

"She was great, a bit of work and she will be a really good sissy slut!" Mark replied.

I stood up and tried to pull my leggings up to cover my erect clit but Rachel caught me. "I see you liked it too sissy!" she said as she grabbed my hard clit through my panties. "Head home now with my husband's cum all over your face like the sissy slut you are. Come back tomorrow evening if you are interested in making this an ongoing thing..." She slapped my ass hard as I turned to go. On the ride home, as Mark's cum dried on my face, I smiled knowing I would be back tomorrow.