A sissy's first time
I was nervous. I wanted it so much and was afraid I would chicken out. I just moved from Seattle to Oakland and found an ad here for a cd/trans sex party and figured it would be perfect because I'd be able to blend in or disappear. I called the host and lied a little - told him I was a little more experienced than I really was. Up to this point I had given many blowjobs and been softly penetrated once by another sissy but never really fucked.
The hostel I was staying in didn't really give me a place to change so the host was was nice and offered to let me come early and use his bathroom. He greeted me at the door, roughly handsome with a very rocker look. I got pretty excited and determined in my mind that at least I'm going to blow him tonight.
No one had arrived but I tried to quickly get ready in the little bathroom as best as a first time sissy on a mission could. When I came out there were a few guys sipping drinks and socializing. In a cheap pink Cleopatra wig, leopard body suit, press-on nails and hastily applied makeup, I looked every bit a trashy sissy compared to the two other beautiful trans women there. I was introduced and we passed around a blunt.
The weed and a little bit of drink loosened up the nerves a bit and after a while the host opened his robe for me and I caught a glimpse of His wonderful thick cock. I couldn't help be mesmerized by it and had to feel it. Soft and heavy in my hands, it got harder and rose up - I was drawn to it and licked it up and down. It tasted better than any of the men I had met in any hotel room before as I sucked him into my mouth. My jaw stretched and I could feel his head pushing into my throat while holding back the tears that inevitably leak out because your head doesn't have room anymore.
The other mean started watching and standing near me, while the ladies began encouraging this new girl. More cocks came out and were pushed towards me and I obliged. My mouth was now a hole for everyone and I was so happy to be pleasing them!
The host pulled me to the mattress on the floor and helped me into position on my knees and hands. He pulled my panties to the side, rubbing my ass and I could feel the cold lube being massaged into it and around my now hard dick. His big fingers pushed into my tight hole and he told everyone just how fucking tight I was. "I thought you said you've done this before" he said as he pushed two fingers in and I could only winch and sorta scream a little no in reply.
Lubed fingers hurt, but not like a horrible pain. No this was a pain that I was wanting - needing - and had to endure. The others taunted me more, telling me that the host was going to tear me up and I won't be the same. They of course were right, but as he removed his fingers and put his cock head to my ass, he asked me if I was ready - I answered by pushing back and feeling a real cock fully enter me for the first time.
This was what I needed. I needed to know my purpose and that it was to be fucked. He was wonderful and gave me time to adjust. Yes, oh it was so uncomfortable. My ass burned even though there was plenty of lube, but as he felt me relaxing and the girls held and comforted me, he started to slowly pull back. Then pushed in...
Someone held a bottle to my nose and I inhaled, the popper quickly had it's affect and my mind started wirring and I loosened enough for him to pull out. He paused for a moment before steadily pushing all the way back in - the pop this time was so wonderful, then feeling his thick veiny head pushing deeper and deeper until I could feel his balls hit mine and at this point the wannabe sissy was transformed into a a real sissy.
His pace picked up and someone's cock was suddenly in my mouth again. I wasn't hard anymore - just a floppy little dicklet. Next to me a guy was fucking one of the girls who was sucking the others big cock but that cock sometimes moved over to me too and I was being fucked from both ends. The hosts pace was unrelenting and I was in ecstasy until he pulled fully out.
They helped my over unto the bed on my back with my legs up. Then another man put on a rubber and pushed in. He commented on how tight I was still and how good I felt. His cock was smaller, but i didn't care. This new position let me see their face and - oh fuck he reached down and put his hand over my throat squeezing ever so slightly. I couldn't breathe for the next few strokes as his eyes rolled back. I wasn't sure what happened as he howled before quickly pulling out. The drink and smoke, plus another sniff of that popper put the world in a spin as I heard something about #2 cumming so hard and one of the girls rolling a condom on #3 then I felt him punch into my fuck hole. He was so much smaller but as he spit in my face and told me what a worthless slag whore I was now, I squeezed every stroke I could determined with whatever I had to give him a good fuck. He couldn't last long anyways and after he pulled out, the host wiped my face off and asked if I wanted to feel him cum inside me.
"Yes Daddy I wanna feel your baby juice" escaped my lips and he smiled. One more hit and he laid me to the side, snuggled up behind me and I felt him slowly enter me.
To this point, everyone wore a condom and it felt great. But feeling skin and the difference in friction... It felt wo wonderful and intimate. He was so good at fucking me and I felt such different feelings inside as he did in this position. He was rubbing this spot and as he increased his pace every twitch in his thick cock was more noticeable. The contact of his skin make his cock feel even thicker, or maybe it was not being constrained by that trojan. Things started accelerating and I could feel somehow my own stirring inside - like an orgasm but much deeper. I couldn't help moaning and he asked if I liked that as he somehow pumped even deeper. This wasn't //like// an orgasm, it was an orgasm, "FUUUUCk yes Oh fuck!" I couldn't stop saying and then iit suddenly got much warmer inside as my host grunted.
Feeling his cum flooding my ass was incredible. Hot, pulsing, silky cum now was lubricating our joining as he fucked me for a few moments, then just held inside me as he softened. "I wanna keep that inside you baby girl," he said and I cooed back, "mmm think you might get me pregnant?" I didn't realize I might have had a breeding kink till then but he certainly had one and now had a little sissy to breed for the next couple years.
The hostel I was staying in didn't really give me a place to change so the host was was nice and offered to let me come early and use his bathroom. He greeted me at the door, roughly handsome with a very rocker look. I got pretty excited and determined in my mind that at least I'm going to blow him tonight.
No one had arrived but I tried to quickly get ready in the little bathroom as best as a first time sissy on a mission could. When I came out there were a few guys sipping drinks and socializing. In a cheap pink Cleopatra wig, leopard body suit, press-on nails and hastily applied makeup, I looked every bit a trashy sissy compared to the two other beautiful trans women there. I was introduced and we passed around a blunt.
The weed and a little bit of drink loosened up the nerves a bit and after a while the host opened his robe for me and I caught a glimpse of His wonderful thick cock. I couldn't help be mesmerized by it and had to feel it. Soft and heavy in my hands, it got harder and rose up - I was drawn to it and licked it up and down. It tasted better than any of the men I had met in any hotel room before as I sucked him into my mouth. My jaw stretched and I could feel his head pushing into my throat while holding back the tears that inevitably leak out because your head doesn't have room anymore.
The other mean started watching and standing near me, while the ladies began encouraging this new girl. More cocks came out and were pushed towards me and I obliged. My mouth was now a hole for everyone and I was so happy to be pleasing them!
The host pulled me to the mattress on the floor and helped me into position on my knees and hands. He pulled my panties to the side, rubbing my ass and I could feel the cold lube being massaged into it and around my now hard dick. His big fingers pushed into my tight hole and he told everyone just how fucking tight I was. "I thought you said you've done this before" he said as he pushed two fingers in and I could only winch and sorta scream a little no in reply.
Lubed fingers hurt, but not like a horrible pain. No this was a pain that I was wanting - needing - and had to endure. The others taunted me more, telling me that the host was going to tear me up and I won't be the same. They of course were right, but as he removed his fingers and put his cock head to my ass, he asked me if I was ready - I answered by pushing back and feeling a real cock fully enter me for the first time.
This was what I needed. I needed to know my purpose and that it was to be fucked. He was wonderful and gave me time to adjust. Yes, oh it was so uncomfortable. My ass burned even though there was plenty of lube, but as he felt me relaxing and the girls held and comforted me, he started to slowly pull back. Then pushed in...
Someone held a bottle to my nose and I inhaled, the popper quickly had it's affect and my mind started wirring and I loosened enough for him to pull out. He paused for a moment before steadily pushing all the way back in - the pop this time was so wonderful, then feeling his thick veiny head pushing deeper and deeper until I could feel his balls hit mine and at this point the wannabe sissy was transformed into a a real sissy.
His pace picked up and someone's cock was suddenly in my mouth again. I wasn't hard anymore - just a floppy little dicklet. Next to me a guy was fucking one of the girls who was sucking the others big cock but that cock sometimes moved over to me too and I was being fucked from both ends. The hosts pace was unrelenting and I was in ecstasy until he pulled fully out.
They helped my over unto the bed on my back with my legs up. Then another man put on a rubber and pushed in. He commented on how tight I was still and how good I felt. His cock was smaller, but i didn't care. This new position let me see their face and - oh fuck he reached down and put his hand over my throat squeezing ever so slightly. I couldn't breathe for the next few strokes as his eyes rolled back. I wasn't sure what happened as he howled before quickly pulling out. The drink and smoke, plus another sniff of that popper put the world in a spin as I heard something about #2 cumming so hard and one of the girls rolling a condom on #3 then I felt him punch into my fuck hole. He was so much smaller but as he spit in my face and told me what a worthless slag whore I was now, I squeezed every stroke I could determined with whatever I had to give him a good fuck. He couldn't last long anyways and after he pulled out, the host wiped my face off and asked if I wanted to feel him cum inside me.
"Yes Daddy I wanna feel your baby juice" escaped my lips and he smiled. One more hit and he laid me to the side, snuggled up behind me and I felt him slowly enter me.
To this point, everyone wore a condom and it felt great. But feeling skin and the difference in friction... It felt wo wonderful and intimate. He was so good at fucking me and I felt such different feelings inside as he did in this position. He was rubbing this spot and as he increased his pace every twitch in his thick cock was more noticeable. The contact of his skin make his cock feel even thicker, or maybe it was not being constrained by that trojan. Things started accelerating and I could feel somehow my own stirring inside - like an orgasm but much deeper. I couldn't help moaning and he asked if I liked that as he somehow pumped even deeper. This wasn't //like// an orgasm, it was an orgasm, "FUUUUCk yes Oh fuck!" I couldn't stop saying and then iit suddenly got much warmer inside as my host grunted.
Feeling his cum flooding my ass was incredible. Hot, pulsing, silky cum now was lubricating our joining as he fucked me for a few moments, then just held inside me as he softened. "I wanna keep that inside you baby girl," he said and I cooed back, "mmm think you might get me pregnant?" I didn't realize I might have had a breeding kink till then but he certainly had one and now had a little sissy to breed for the next couple years.
3年前
