I have been in and out jails, and prison until my
Hi, Im Sarah, I’ve been dressing on and off for years, but mostly since my last breakup and becoming single three years ago. While I’ve had fun over the years with other tgirls at clubs, I’d never been brave enough to go all the way and have intercourse until early this year with a tgirl. I started out as a lesbian tgirl, but for the last few months I have found myself becoming attracted to the idea of being with an older dominant man. Now this happened yesterday xxx
I got a message from a man on Fabguys, complimenting my pics. I’d replied with a polite thank you, then read through his profile, read his verifications from mainly other tgirls, and looked at the pics. Mainly of tgirls on all four with a dildo in their pussy. The verifications from those girls were hot, describing him as a genuine, Dominant man that knows how to treat a submissive sissy and I was intrigued.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
I got another message from him saying hi, and asking about me, what I’m into and what I’m looking for. I replied with some details about me, past experiences, and what I’m hoping to do. Well messages back and forth during the day as I was at work, and he asked if I’d like to meet. I told him I’d love to, that I’m free the following afternoon, but cannot accommodate as live in a houseshare. We agreed on a hotel not far from me. I told him I’d be there at 5 but need a bit of time to shower, shave and get ready.
As he was driving down from north London, he said to text him the room number when I check in, and he’ll set off.
Well the next day I worked the morning, finished at 3, grabbed my stuff and made my way to the hotel. Stopped in a Pub for a couple of drinks just to calm my nerves. I was a wreck!!! Had a couple of drinks, then suddenly told myself right, time to go and do this! I am not chickening out! So off I went, checked in, got to the room, and texted him the number. He replied he’ll leave his place in a few minutes, and will take him just over an hour to arrive. Suddenly I felt nervous again. What was I doing!!! Luckily I had a bottle of cider so had a drink, and went to the shower to get ready.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
You girls know the drill. Hot shower, shave, drying up. Once out I had already laid out my outfit on the bed. I was going for a new black bra and panty set, garter with stockings, black heels, red wig android silky blouse that’s so short there’s no way to cover the stocking tops xxxx once made up and dressed I looked in the mirror, and thought I look like a hooker (perfect).
Checked my phone and message saying he’ll be there in 5mins. I messaged him saying knock on the door and I’ll let him in. Knock knock (OMG my heart was pounding). I opened up and let him in. A good looking man, solid build, friendly smile. He said I looked fabulous (blush) and gave me a peck on the cheek, while his hand did pat me on the bum Hmmmm (big hands)
We sat down chatting for a bit, talking about ourselves but the whole time I was waiting for him to make a move. He got up, told me to come over and he embraced me, and thus time kissed me on the lips. That was it, something switched on and my mouth opened and soon we were tongue wrestling with his hands groping me all over. I love the feeling of a man holding me tight and running his hands all over my body. Foreplay is so sensual and sexy it makes me feel so submissive and womanly. We ended up on the bed where I helped him take off his trousers and pants, and saw his cock which was half erect but already looked thick!
sissy crossdresser sucking a nice cock
I got between his legs and took his warm cock in my mouth, and started sucking. It’d been so long since I had a cock in my mouth, I went to town on him. I started gently licking the shaft from top to bottom and teasingly taking into my wet mouth as it started to get fully stiff. From the moans he was making I guess he was enjoying it I easily spent the next 15 mins just sucking, feeling him getting harder and harder in my mouth. He held my hair as he started to gently face fuck me. Pushing that wonderful cock all the way into my willing throat.
He made me stop and told me to get on the bed on all fours. Taking his time he watched me as I got into the submissive position. He pushed my legs apart and started to feel up and down my thighs, touching my cock every now and again. He ran his hands over my silky panties and pressed against the warmth of my sissy pussy and then pushing my shoulders down so that my bottom was high in the air. Displayed for his enjoyment.
My dress was already above my bum, as he started to pull my panties down just below my buttocks. My sissy cock was dripping into the material at the front. He knows I’m a relative virgin and I was relieved to feel him smearing some some lube in my hole and inserting a finger or two stretching me. The dildo had been well lubricated and he started opening me up with it. It felt wonderful as he pushed it in and out of me each stroke going a little deeper than the last.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
My legs nearly gave way when he switched the dildo on and it started to vibrate. My whole body seemed to be electric to his touch as the dildo did its work. Once it was fully inside me he pulled my panties back up to hold it in place. He stepped back to admire his work. There I was, dressed in my sluttiest outfit on a hotel bed with my legs apart and a stranger had filled my sissy hole with a vibrating dildo. I heard the click of a camera as he took photos and this was soon followed by the feel of a paddle rubbing over my cheeks.
He started to spank me, alternating between each cheek. Softly at first, but then the spanks got harder as my punishment progressed. Oh my it felt amazing being spanked in that position with a buzzing toy in my pussy. He spanked me until he decided I had taken enough swats, which is just as well as I was squirming and yelling towards the end of my ordeal. A few minutes while he rubbed my red and well marked cheeks and then he came to the front and offered his cock again to my waiting mouth, keeping him nice and hard.
He told me to go and put my other outfit on (I’d just got a new Japanese schoolgirl style outfit that I’d not tried yet), so I went to the bathroom and got changed. This time black wig, black panties with a heart shape cut out in the back, and the uniform. When ready I came out and he said its looked so cute xxx
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
I got down on my knees and started sucking him again, his hands holding my head as I was getting him hard. He kept saying how good a cock sucker I was, which made suck harder xxxx. He told me to get on the bed on all fours again, and again the dildo was thrust inside me. Deep this time with no build-up. I gasped as my red raw hole opened and took it all in. All accompanied by his firm hands spanking my already burning cheeks this time.
I was loving the mixture of being filled…the pleasure and the pain sending me into a new dimension as he used me as his fuck toy.. Suddenly he pulled the dildo out and I felt something hard and hot at my hole. OMG this was it! I was going to be deflowered!!!
He asked me do I want him to fuck me, I said yes in a low voice. He asked again, so I said yes, much louder! I would have done anything at that stage to keep the pleasure going.the head of his cock pushed at my hole and with a firm puc=sh from his hips the bell end burst into me. The combination of the dildo and lube had been good so that it didn’t hurt much. Just a hot streched stab. He left it there for a minute as my body got used to this new invasion.
Slowly and deliberately he put his hands either side of mu hips and grabbed my flesh making sur I couldn’t move as he started to slide himself into me. While his cock isn’t very long, it is quite thick and it took a few seconds of pushing before he got it in, and OMG it was amazing. I was a woman at last. The feeling of a real cock deep inside me was overwhelming.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
He laid down on top of me flat on the bed and started to fuck me. I was in sissy heavens he started pumping into me. He was relentless his cock poisoning in and out of me as I kept begging him to keep fucking me. Fuck me hard…make me your slut!
I felt him start to grow even bigger as his pace picked up. His cock getting hotter as he used me like a rag doll for his lust. He asked me where do I want him to cum, I said please cum on me. He pulled out of me and I felt my pussy gaping as he rolled meant my back.Lifting my legs, he bent me up so that my ankles were beside my head and he was soon back inside me again. Now he was like a wild a****l fucking my poor stretched pussy harder and faster. this time pumping me deeper, harder and faster.
I could actually feel him getting harder then he pulled out and with a shout of ecstasy his cock sprayed hot cum all over my hole, on my clit and over my chest. He seemed to cum for ages spurt after spurt covering the whole of my body. Calm now, he looked down at me and smiled and noticed my own little cockette which was now hard and standing proud. He covered it in lube and gently wanked it until, after only a few minutes, I too shot my pathetic load into his hand. He fed me my own cum and kissed me as we recovered form our experience.
We sat and chatted a bit more, promised to stay in touch and hope to do it again. Definitely xxx
I got a message from a man on Fabguys, complimenting my pics. I’d replied with a polite thank you, then read through his profile, read his verifications from mainly other tgirls, and looked at the pics. Mainly of tgirls on all four with a dildo in their pussy. The verifications from those girls were hot, describing him as a genuine, Dominant man that knows how to treat a submissive sissy and I was intrigued.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
I got another message from him saying hi, and asking about me, what I’m into and what I’m looking for. I replied with some details about me, past experiences, and what I’m hoping to do. Well messages back and forth during the day as I was at work, and he asked if I’d like to meet. I told him I’d love to, that I’m free the following afternoon, but cannot accommodate as live in a houseshare. We agreed on a hotel not far from me. I told him I’d be there at 5 but need a bit of time to shower, shave and get ready.
As he was driving down from north London, he said to text him the room number when I check in, and he’ll set off.
Well the next day I worked the morning, finished at 3, grabbed my stuff and made my way to the hotel. Stopped in a Pub for a couple of drinks just to calm my nerves. I was a wreck!!! Had a couple of drinks, then suddenly told myself right, time to go and do this! I am not chickening out! So off I went, checked in, got to the room, and texted him the number. He replied he’ll leave his place in a few minutes, and will take him just over an hour to arrive. Suddenly I felt nervous again. What was I doing!!! Luckily I had a bottle of cider so had a drink, and went to the shower to get ready.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
You girls know the drill. Hot shower, shave, drying up. Once out I had already laid out my outfit on the bed. I was going for a new black bra and panty set, garter with stockings, black heels, red wig android silky blouse that’s so short there’s no way to cover the stocking tops xxxx once made up and dressed I looked in the mirror, and thought I look like a hooker (perfect).
Checked my phone and message saying he’ll be there in 5mins. I messaged him saying knock on the door and I’ll let him in. Knock knock (OMG my heart was pounding). I opened up and let him in. A good looking man, solid build, friendly smile. He said I looked fabulous (blush) and gave me a peck on the cheek, while his hand did pat me on the bum Hmmmm (big hands)
We sat down chatting for a bit, talking about ourselves but the whole time I was waiting for him to make a move. He got up, told me to come over and he embraced me, and thus time kissed me on the lips. That was it, something switched on and my mouth opened and soon we were tongue wrestling with his hands groping me all over. I love the feeling of a man holding me tight and running his hands all over my body. Foreplay is so sensual and sexy it makes me feel so submissive and womanly. We ended up on the bed where I helped him take off his trousers and pants, and saw his cock which was half erect but already looked thick!
sissy crossdresser sucking a nice cock
I got between his legs and took his warm cock in my mouth, and started sucking. It’d been so long since I had a cock in my mouth, I went to town on him. I started gently licking the shaft from top to bottom and teasingly taking into my wet mouth as it started to get fully stiff. From the moans he was making I guess he was enjoying it I easily spent the next 15 mins just sucking, feeling him getting harder and harder in my mouth. He held my hair as he started to gently face fuck me. Pushing that wonderful cock all the way into my willing throat.
He made me stop and told me to get on the bed on all fours. Taking his time he watched me as I got into the submissive position. He pushed my legs apart and started to feel up and down my thighs, touching my cock every now and again. He ran his hands over my silky panties and pressed against the warmth of my sissy pussy and then pushing my shoulders down so that my bottom was high in the air. Displayed for his enjoyment.
My dress was already above my bum, as he started to pull my panties down just below my buttocks. My sissy cock was dripping into the material at the front. He knows I’m a relative virgin and I was relieved to feel him smearing some some lube in my hole and inserting a finger or two stretching me. The dildo had been well lubricated and he started opening me up with it. It felt wonderful as he pushed it in and out of me each stroke going a little deeper than the last.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
My legs nearly gave way when he switched the dildo on and it started to vibrate. My whole body seemed to be electric to his touch as the dildo did its work. Once it was fully inside me he pulled my panties back up to hold it in place. He stepped back to admire his work. There I was, dressed in my sluttiest outfit on a hotel bed with my legs apart and a stranger had filled my sissy hole with a vibrating dildo. I heard the click of a camera as he took photos and this was soon followed by the feel of a paddle rubbing over my cheeks.
He started to spank me, alternating between each cheek. Softly at first, but then the spanks got harder as my punishment progressed. Oh my it felt amazing being spanked in that position with a buzzing toy in my pussy. He spanked me until he decided I had taken enough swats, which is just as well as I was squirming and yelling towards the end of my ordeal. A few minutes while he rubbed my red and well marked cheeks and then he came to the front and offered his cock again to my waiting mouth, keeping him nice and hard.
He told me to go and put my other outfit on (I’d just got a new Japanese schoolgirl style outfit that I’d not tried yet), so I went to the bathroom and got changed. This time black wig, black panties with a heart shape cut out in the back, and the uniform. When ready I came out and he said its looked so cute xxx
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
I got down on my knees and started sucking him again, his hands holding my head as I was getting him hard. He kept saying how good a cock sucker I was, which made suck harder xxxx. He told me to get on the bed on all fours again, and again the dildo was thrust inside me. Deep this time with no build-up. I gasped as my red raw hole opened and took it all in. All accompanied by his firm hands spanking my already burning cheeks this time.
I was loving the mixture of being filled…the pleasure and the pain sending me into a new dimension as he used me as his fuck toy.. Suddenly he pulled the dildo out and I felt something hard and hot at my hole. OMG this was it! I was going to be deflowered!!!
He asked me do I want him to fuck me, I said yes in a low voice. He asked again, so I said yes, much louder! I would have done anything at that stage to keep the pleasure going.the head of his cock pushed at my hole and with a firm puc=sh from his hips the bell end burst into me. The combination of the dildo and lube had been good so that it didn’t hurt much. Just a hot streched stab. He left it there for a minute as my body got used to this new invasion.
Slowly and deliberately he put his hands either side of mu hips and grabbed my flesh making sur I couldn’t move as he started to slide himself into me. While his cock isn’t very long, it is quite thick and it took a few seconds of pushing before he got it in, and OMG it was amazing. I was a woman at last. The feeling of a real cock deep inside me was overwhelming.
Sarah Meets Her First Master In A Hotel, Sissy Photo Stories
He laid down on top of me flat on the bed and started to fuck me. I was in sissy heavens he started pumping into me. He was relentless his cock poisoning in and out of me as I kept begging him to keep fucking me. Fuck me hard…make me your slut!
I felt him start to grow even bigger as his pace picked up. His cock getting hotter as he used me like a rag doll for his lust. He asked me where do I want him to cum, I said please cum on me. He pulled out of me and I felt my pussy gaping as he rolled meant my back.Lifting my legs, he bent me up so that my ankles were beside my head and he was soon back inside me again. Now he was like a wild a****l fucking my poor stretched pussy harder and faster. this time pumping me deeper, harder and faster.
I could actually feel him getting harder then he pulled out and with a shout of ecstasy his cock sprayed hot cum all over my hole, on my clit and over my chest. He seemed to cum for ages spurt after spurt covering the whole of my body. Calm now, he looked down at me and smiled and noticed my own little cockette which was now hard and standing proud. He covered it in lube and gently wanked it until, after only a few minutes, I too shot my pathetic load into his hand. He fed me my own cum and kissed me as we recovered form our experience.
We sat and chatted a bit more, promised to stay in touch and hope to do it again. Definitely xxx
3 years ago