Sissy Love free porn video

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I opened the door. She was there, wearing her chocolate-colored long raincoat, pearl choker and earrings with brunette curly wig, made up and right in front of me. I smiled like the cat who had the cream (and I was hoping to have that soon!) and stood back as walked in. I was in my sheer pink nightgown with red bra and panties, stockers and garters, tottering in shiny black heels. "My own sissy!" I said to Regina and we kissed, our lips slithering against each other, smearing our carefully applied gloss. I peeled off her raincoat to reveal her black bra and shiny, sheer pantyhose, complete with erection pressed to her hairless, flat belly, wetly stained at the tip. "Pleased to see me?" I caressed her cock through her hose. Leaning forward, I licked her ear and whispered, "Did you miss me, sissy? Practicing with your toys? I should have locked you up, you naughty girl." I gently pushed her away and led her by the hand into the living room. I bent over the back of the sofa. "Lift my gown up and sniff, Regina." She was on her knees in a flash. Regina loved to be told what to do. Funnily enough, outside of the bedroom in her sissy gear Reggie was an overpowering bore, his braggadocio hiding his real nature. But as Regina, she was compliant, sexy and willing to experiment. Lucky for me... She lifted my gown over my ass and put her nose into my satin panty- covered crack. She sniffed, holding my thighs, and let her hands caress my legs. I spread my legs apart to give her more room. "Good girl. Lick the exposed skin of my ass. Kiss." I let her worship and lick for a few minutes then reached back and pulled aside the thin strip of satin covering my hole. "Tease my ass with your talented tongue, Regina. Lick all around my hole. Ah, yes, like that. Can you taste my lube? Do you want to pull your hose down and fuck me, Regina? No...stick your tongue in instead, good girl. Yes...oh! Yes, that's in, right in..." Mmm, I loved when she rims me, she's so enthusiastic. I stood up and turned around. "Pull down my panties. Now kiss just the head. French kiss, lick, OK suck the head - enough! Lick down the shaft, now lick below. Yes, suck my balls, ooh, nice, yes..." I let her work me over. She's well trained, patient but willing, careful and sexy. I love playing with other sissies. "Let's get comfortable." Regina followed me into the bedroom. I had invested in some kinky furniture including a seat with a dildo. "Strip, keep on your bra, then suck your friend." She quickly stripped then sucked the dildo below the open seat of the upholstered chair. "Stop." She lifted her head and I nodded at the bottle of lube which she applied to the dildo. She sat down and I rotated the wheel to push the dildo up her ass, slowly. Regina was used to it by now but still gasped as it entered her. I quickly stripped off, keeping my bra on with my breast inserts. I loved how they jiggled as I moved. I knelt down on a cushion in front of Regina and covered my hands in the sweet-smelling lube. "How long has it been? Have you been faithful, Regina? Not fucked your sweet wife, saving yourself for me?" I rubbed the lube over her rampant cock, careful not to apply any pressure. "Five days, Shelly. I've been good. Lots of late nights watching the porn you specified, the videos and photos, all the stories. Edging. Fucking myself, sucking my dildos, pretending they were you..." Regina was slowly moving up and down on her seat, fucking herself as I toyed with her cock. "Ah, good girl. Is this nice?" I stroked her a few times and suddenly stopped, pushing hard on her thighs so she was fully impaled on the cock in her ass. "You're such a little sissy, Regina. Cock up your ass. What you need is one in your mouth." I stood up and she practically swallowed me down to my balls. I'm not massive but at least seven inches and quite thick. "Oh, you've been practicing a lot!" I started to fuck her face, holding her head as I pushed in and out. I wanted a more personal service so pulled out completely. "Remember how I taught you? Look at me, suck the tip, use your tongue. Make me feel your excitement, your desperation. A cock in your ass and one in your mouth. Make me come all over your face." She started bouncing on the cock again while sucking and licking me, her hand wrapped around the shaft as she batted her eyes, moaning around my cock. I was close...damn she was good. Definitely desperate. "Stop! Off. Hands and knees." She eased off her seat and put her head down on the carpet, ass held high, remembering her training. Regina had lost a lot of weight and her glut exercises had paid great dividends, her once huge, flabby ass now still large but firm and inviting. Especially as she twerked it, inviting me in. I didn't wait for a better invite and moved behind her. "Do you want this, sissy? Do you want to be fucked by my cock? Do you want a man to fuck your ass, Regina?" She knew by now that she'd have to beg. "Please, Shelly, fuck my ass. Fuck me hard. I need your cock inside me, oh please...fill me with your cock, fuck me, please..." I was too horny to tease her for long as I rubbed myself up and down her crack. I could just finish here I thought but it would be so much better inside. I shoved in quickly, her ass lubed and stretched from the dildo, and held her greasy hips as I pushed in hard and stopped, filling her up. She gasped and squealed. "Suck, you fag." I pushed three fingers into her mouth and she sucked them. I pulled them out and pinched her nipple hard, then pulled out until only the head was in, and pushed back in slowly. I established a slow, deep rhythm, pulling on her balls every few strokes but ignoring her dripping cock. After a few minutes I pushed in deep then stopped moving, leaning over and hugging her to me, biting her back and running my hands up and down her flanks and her legs. I knew we were both close. I wanted to show my affection; this wasn't just about sex, I loved spending time with Regina and wanted to show her that it was more than just the purely physical act. I had learned long ago that affectionless sex was not satisfying, at least for me. The act of love needed a bit of loving. But spice is always nice as well. "You ready for me, girl?" Regina whimpered so I straightened up and started pushing in and out again, deep strokes, speeding up until I was slamming into her, our balls hitting on each stroke, 'slap slap slap' as I pushed in. I let myself go, pushing hard as I could, raking my nails down her back until I was there and pummeled her over and over, slapping her back and ass as I growled and yelled, Regina letting a constant stream of, "Uh, uh, uh, uh..." escape from her lips as I emptied myself deep inside her lovely ass. I caught my breath and fell on top of Regina, then rolled her over so we were facing each other and we kissed. She hadn't come yet and I could feel her hardness poking into me but I ignored it and traced her ears and lips with my fingertips. My sissy lover, all mine. It was glorious. "You're so good, Regina. I'm yours. It's been a long time. Fuck me. I want you inside." I knew she wouldn't last long but that was OK, we had all night and the next day as well. She'd done well - when we first got together she came in her pants as we kissed. I take it as a compliment, especially when I fed her all of her creamy leavings off my fingers. I decided I wanted to ride her so I simply moved down and guided her inside me. Oh, it had been a while and it was splendid, so satisfying as I pushed down and felt her fill me up. Regina wasn't terribly big but fine for me, I'm no size queen. I pulled her head up while leaning over and we shared a fierce kiss, then I straightened up and slowly moved side to side and up and down, enjoying Regina below me. She was close so I leaned down again and pinched both her nipples hard and started to bounce up and down, hard. It only took a few seconds until she was screaming and grabbing my arms as she spurted over and over as I kept moving up and down. I kept it up until finally she slipped out. I laid down next to Regina and we cuddled and kissed and stroked each other. I was a little sore but it was a wonderful feeling as we enjoyed our post-coital time with little kisses and touches. "So, darling, was it nice coming inside my ass? I loved gripping you tight as I rode you. Watching your face as I pinched your nipples and you exploded deep inside my ass. Was it worth it, edging for nearly a week, no release?" "Shelly, it was bliss. Feeling you on top of me, riding me, controlling me even as I was buried deep inside you. Oh and when you made me come, I never felt so complete. Both times...with you pounding me from behind, it hurt so good, sweat flying off each time you slammed into me, over and over..." Suddenly Regina was crying. I held her tight and whispered that it's OK. Finally she stopped and said, "I'm sorry, it's just so perfect, and I know I have to go back, why can't I stay, I, I'll..." "You know it can't be my love. But we can improve your life. You know we discussed this. Gloria isn't old and hasn't dried up. Go down on her, worship her body, her curves. Spend time down there. Lick her ass like you do mine. Tell her that you've been watching porn and you've discovered another side to your sexuality, that you want to pleasure her instead of yourself. Don't finish yourself, just concentrate on her. It'll be a step up from porn and edging solo. Don't refuse her if she wants to fuck, but your only priority is her. Not necessarily every night but as much as she'll allow - she'll be begging for it after a week. Get a Magic Wand and use it on her as you go down on her. No, I mean it - otherwise this won't work. I'm not breaking up another couple." We had a fantastic time the rest of her stay, used more toys and fucked and sucked ourselves until we could barely move. And my plan worked, but only because Regina/Reggie was so good at following my orders. Gloria cancelled a series of get-togethers and her girlfriends thought she was sick, but she just wanted to stay in bed with Reggie. There was very little edging involved as Gloria grew to love being on top, same as I did, especially afterwards when Reggie would go down on her again and suck out all his own come. A happy ending? Definitely for my lover who had the best of both worlds. Me, well, I had Regina occasionally and made up for lost time with my friends Dee, Clair and a few others. Who said getting old wasn't for sissies?

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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

2 years 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
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

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