Rosies first time. part 1

As a submisive BI crossdresser, l was an anal and oral virgin. I had a FemDomme friend who l saw on a regular basis. She typically would spank me and Dominate me in the usual manner while l was dressed as Rosie. Then one day she told me she had a surprise for me... she left the room and returned wearing a strap on dildo... it was about 7" long and not real thick and she informed me I was going to become a "real" woman and learn to suck cock! She threw a pillow onto the floor and commanded me to my knees. She started to rub the tip of the strap on around my lips and told me to kiss it and lick the tip which l did. Holding the back of my head so l couldn't pull back, she slowly pushed it past my lips and over my teeth into my mouth... at first it was difficult to keep in my mouth comfortably as she was rocking back and forth penetrating my face in ways l never imagined. Soon it was in about half way and l was finding it difficult to breathe around it. She told me to concentrate on breathing through my nose which l did and soon found it much easier. As she slowly fucked my mouth, l began to get used to the texture and taste of the rubber. once my mouth became wet and slobbery with saliva it made it much easier to slide into my face. I could feel my clitty geting hard and excited and shortly cum in my panties. Mistress knew from my noises that l was making that l had cum so she put me down on my hands and knees and paddled me with 50 strokes of her hairbrush. Then pulling my cum soaked panties off and putting them over my head with the cum soaked area over my face, she gave me a dozen with her heavy cane, leaving severe welts on my poor bottom!

"Now", she said, as l heard the snap of a rubber glove around her wrist... "I had really wanted to save this for another session, but since you cannot seem to control your slutty desires l am going to start training your bottom also. Get up and bend over the horse," she odered. "And remove your panties and hand them to me"! As l took them off my heat she wadded them up with the cum side out and stuffed them into my mouth! Using a short leather strap she effectively gagged me wth my own cum soaked panties! "Spread your cheeks", she odered and as l did, l could feel the coolness of the lube being poured on my butt crack. Soon l felt the pressure of her gloved fingertip pressing against my virgin pink rosebud. I winced slightly as it briefly penetrated my anus and then was withdrawn. Again and again it probed my private parts, until she had worked the entire digit into ma as deeply as it would go. Soon a second finger joined the first and she commenced to open up my asspussy as far as it would stretch. Pumping it in and out, she had me moaning and thrusting back against her hand. My clitty was starting to get hard again and l had to really concentrate to not cum again without her permission! Just as l reached the point where l thought l could not stand any more, she slowly and sensually removed her fingers.

She then said, "Rosie, l am so proud of you... I know how close you were to cumming, but managed to keep it under control. I am now going to fuck your ass with this strap on and you may cum as much as you desire". I could feel the head of the dildo pushing it way into my orifice and with a slight POP it entered me...there was a brief flash of pain but then it began to feel incredible as she thrust it deeper into me, going further each tme until l could feel the balls pounding on me. Her nylons were rubbing against mine and making that sexy swishing sound! I was sooooo turned on my legs felt like jelly and l woul have collapsed if l hadn't been supported by the horse. I had been concentrating on not cumming so it would last longer, but my little clitty cock betrayed me and soon I began to cum harder and longer than l had ever done before !!!

As Mistress unbuckled the strap holding my cummy panties in my mouth, she told me that l needed to wear them home and keep them on until the cum was dry before l could take them off... which l happily did...
A true Story by Rosie Dahl




Part 2 to follow soon! More sissie training!