The Sissy Trainer Part 2 – Taking A Virgin free porn video

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Ken raising my dress higher to have a better view of “loosening me up” and told me to rest my heels over the other end of the couch. As he fingered my butthole, his hard cock continued to slap against the side of my body as he wiggled and shook his finger. The more I thought about Ken finally ramming his cock in my tight butthole the harder I clinched. “Lisa, I need you to relax some, take a deep breath” “Ken” I asked “Is it going to hurt much?” “You are super tight, but I brought lots of lube…I think you’ll be fine.” “Thank you” I whispered. Ken pulled out his finger. “You know this is not going to be pain-free, but you wanted this, remember that.” I nodded my head and quietly said okay. With that Ken spanked my butt and said let’s go to the bedroom.

I stood up, adjusted my dress again and ran my hand through my hair. Ken looked down at my rock hard clitty, I blushed twirled my hair behind my ear. “I hope you don’t mind me saying that you look like a beautiful slutty fat whore” I smiled and folded my hands behind my back. “Does that mean that you will be extra gentle?” I said coyly, “No, it just means that I will enjoy it more.” I took his hand and walked him to the bedroom while peeking back at the purple head of his cock bobbing up and down as he walked. Just the thought of it invading me made me again brush my hair behind my ears again. The closer we were getting to the event the more feminine I was becoming. I thought about how I looked to him as he was about to take another virgin butthole. I walked slowly so he could take in the full picture of me from the back. Chubby brown gurl, smooth chocolate skin, black tight tube dress just covering my butt, shoulder length black hair with red highlights, black mules with pink heels, thigh-high nylons with little bows in back. I dressed slutty for him and by the look of his hard cock, he liked it, he was looking forward to busting my cherry and hearing my squeals. Once we got to my room Ken scanned the little 5- inch vibrators and lotions on my dresser. “I think when we are done you are going to need bigger toys” he chuckled, oh boy I thought.

Ken kissed the back of my neck and whispered in my ear if I ever had my ass licked before? “Yeah, years ago when I was younger at summer camp, an older counselor gave me a couple pf beers, I got sleepy I laid on the bed in his office. He pulled down my shorts and felt him licking me back there.” “Did you like it?” I smiled and said yes. He told me to get on the bed on all fours. I climbed up, faced the headboard, hung my feet over the side. His hands forcefully spread my meaty ass-cheeks; then I felt the gentle kiss of his lips touching my hole and he began licking my ass. His licking was strong and lusty. He then pushed my back down further and raised my hips more to fully expose my virgin butthole to his tongue. All the time he was stroking my hard dicky. I stiffened, but he pushed his tongue deeper in me, and the slickness of his spit pool in my wet ass helped it in. It was delightful to feel is hot breath on my asshole and balls. The feeling of Ken making out with my butthole and stroking my hard little dicky yet me moaning. “Oh God, oh God, oh God, please...” “Please what?” he asked “Please let me cum” I moaned. Ken grabbed my waist and power lifted my back-half off the bed, I had to quickly balance my remaining weight on my elbows. Ken held half my body in the air as he tongue-fucked me. I had no idea how he easily bench-pressed my fat ass like it weighted nothing, I just know I never wanted him to stop. My heels twirled and rolled and once he started licking my balls my eyes rolled to the back of my head. “Please, please, please let me cum” I begged.

To be continued…

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Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

2 years ago
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Andrew The Unsuspecting Sissy Part VII

ANDREW THE UNSUSPECTING SISSY PART VII [email protected] *** A NOTE TO ANDREWS' FANS: I DON'T GET VERY MUCH FEEDBACK, PERHAPS 4 OR 5 PEOPLE WITH EACH CHAPTER. WHILE I APPRECIATE THE SUPPORT FROM THOSE THAT ENJOY THE STORY, I CAN'T SEE CONTINUING THE TALE IF SEEMINGLY VERY FEW PEOPLE ARE INTERESTED. SO, IF YOU ENJOY THE STORY, OR DON'T, PLEASE LET ME KNOW! MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN...

3 years ago
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Maid to Measure or Sissy Slave by Deesign Part 3

With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...

1 year ago
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Britney loses her Sissy Virginity

We had chatted online and I agreed to meet him at his place, I was ready to take the step to live action and he was very hot and hung. I arrived and he led me to the bathroom to get dressed and made up, "See you in a few,Sweety" he said, I was already feeling gurly just by the sweety remark. I put on my cutest pnk plaid school gurl skirt, white stockings and pink satin panties, made up my face with some very hot red cocksucker lipstick, eyeliner and blush. I was so nervous, yet so horny. I took...

1 year ago
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A sissy called Jezebel Part XX

A sissy called Jezebel Part XX - Jezebel and hir entire family next attend a family wedding, where the bride is a sissy (of course.) What sexy, submissive traditions prepare the beautiful blushing bride for hir big day? Will our bride vow to love, cherish and (especially) obey, all orders, whims, without any hesitation, from hir goddess/wife/mistress and to her complete and utter satisfaction? There is non-stop teasing in the car about the bridesmaid dress. Everyone knows I adore...

1 year ago
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My Sissy Life Part 17

My Sissy Life Part 17 I fixed my make up and went back to cleaning, I didn't want to get into trouble because my chores weren't done. I don't know how I would explain that, 'I'm sorry mother I couldn't finish dusting because I was too busy sucking Jake's cock.'. That is not a conversation I wanted to have. I wasn't sure what was going to happen when Jake babysat me for the weekend. I had an idea that there would be a repeat of what just happened. The rest of the night. I served...

3 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Mein erstes Mal als Sissy Part 10

Fortsetzung von:https://de.xhamster.com/stories/mein-erstes-mal-als-sissy-part-9-708712„Hallo meine kleine Schlampe“, begrüßt er mich nachdem er mich ein Zeit lang mehr oder weniger ignorierte. „Nun kommen wir zu meinem persönlichen Höhepunkt des Wochenendes“, er führt mich nochmal ins Bad und legt mir Dessous in Rot bereit, dazu ein rotes Negligees, die blonde Perücke lasse ich auf und er bittet mich, dass ich mich ganz nuttig für ihn zu Recht mache. Ich freue mich darauf endlich wieder von...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
3 years ago
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Rubber Sissy Panties Part 2

Rubber Sissy Panties Part II Clark woke up at work. He was dressed in the same clothes as in the previous day, shaven and the clothes were clean and ironed to perfection. He looked at the clock on his computer, and it was 7am, way earlier than anyone else would be hanging around. He raised himself off his chair and walked to the W/C, ready to relieve his full bladder. Not noticing his own behavior, he lowers his pants and sits down on the toilet, and points his sissy clitty...

4 years ago
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Blackmailed Sissy Whore Part Three

Blackmailed Sissy Whore Part 3 I did manage to get a little sleep. After Tiffany finally zonked out, and the continual grinding on my thigh and the relentless playing with my nipple rings stopped, I couldn't keep my eyes open any longer. Friday night was the last full night's sleep I had gotten since Marcus took over my computer, and my life. I woke up before my alarm went off, which was a good thing. I was tangled up in limbs so securely, it took me several minutes to snake my way...

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