Toni Begins to Come Out

Story Info
This is my second part of my dressing and changing.
2.7k words
4.42
19.7k
11
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
CutieToni
CutieToni
19 Followers

After getting my cherry broke by a ten-inch cock all I could think of was how good it would have felt to feel him cum inside me and seeing his face as pleasure took over. Knowing my little pussy was good enough to make a man cum made me excited. Having a man cum inside sounded so kinky and would make me so lady like. I wanted this more than anything even though I wanted to suck a man to completion and swallow him, I was torn which I wanted most. Again all these thoughts only happened after I was dressed and ready to be Toni for the night. I still couldn't stand the thought of a man touching me when I wasn't dressed.

The next weekend I was ready and a man contacted me that was dying to be with me, but it turned out he couldn't get hard enough to fuck me but I learned something about myself I didn't know. Because of this experience I realized I had to say yes to everything because I was going to learn something new about myself every time. And this was when my list took on a whole new approach.

I told him as long as he would fuck me I'd let him come. He said he would and about an hour later he arrived, this was on a Saturday morning which to be honest felt strange to be doing all this in the day light. When he came in he was carrying this bag, I had no idea what was in it. He sat down next to me on the couch and made me blush with all the things he was saying, I still wasn't used to hearing these kinds of things from another man. Telling me how hot I was, and how much my big tits turned him on. He was rubbing them as he'd say these things. His other hand went up my skirt and began playing with me, he was very good with that! He knew just how to tickle my balls and lightly brush the underside of my cock, I got hot and ready quick.

I said "fuck me" and he reach down and took his bag and head off to the kitchen. I didn't know what was going on. The kitchen and living room were only separated by a bar so I walked over to the bar and watched as he pulled out a penis pump, I'd never seen one before and didn't know what it was for until he started using. I watched has he used it and I have to be honest, watching him was hot. When he got finished he told me to get in the floor on my hands and knees. I have a very tight pussy so a man had to be really hard to get in me and he was at first but with his effort of trying to get in me he lost his hard-on. He went back and pumped up again and tried another time. After several tries I was so horny I'd fucked anything.

He was over pumping up again so I went to my bedroom and brought my dildo back. The only one I had at the time. It had a suction cup and I liked sticking it to the coffee table and fucking myself and I did just that. I sat back on it and when it slid in me I practically yelled OH MY GOOD THAT FEELS GOOD! This caught his attention. He walked over and stood next to me as I rode it up and down. I then laid back and began fucking it and stroking my cock. I looked up and his eyes were fixed on me and I got really excited this was the first time ANYBODY had ever seen fucking myself and jacking off I really got excited about him watching and I went wild fucking myself. I watched his face as I started cuming and when I seen he liked it I think I came more. This is when I realized I really liked being watched. Knowing he was watching made me cum very hard. I knew then I'd found another kinky thing I liked, I loved being watched. Immediately after he left I changed my ad to read, if you just want to watch me masturbate you can, but I also added if you have any fantasy you'd like to try no matter how bad it seems I'll help, I thought this would be a good way to try new and wild things and boy did it ever, but it also led to some very bad things. It caused me to do things I'd never done in a million years and it also started some crazy fetishes I had. Some of the things I did I liked and did many more times, even when I masturbated.

That very afternoon I was horny again which wasn't entirely unusual for me but it was the first time I redressed. I was wanting someone to fuck me and cum in me so I could see if it felt as good as I thought. So I began answering emails hoping that someone would come and give me what I wanted. And the first one that said he could come that day was a man that I think changed me as much as anyone. He'd emailed twice before but we couldn't get our timing wright. I told him only if he could come and fuck me and cum inside me. He said he'd try but he had trouble getting hard enough. He said he'd only been with one other man and that was years ago when he was much younger. He said they only jacked each other off but he'd always wanted to do more. He also told me he wants to bring his wife's sexy nighty and us play together while he wore it. This sounded kinky enough for me, besides, I thought if he couldn't get hard enough to fuck me I give him a blow job and experience the first man cuming in mouth. That was high on the list as well.

He came in and went to straight to the bathroom to get ready. I went to the couch and waited. When he came into the Livingroom he looked SO sexy! He had on this little blue nighty with a pair of small panties. I could see his cock and it was already semi hard. When he sat down on the couch he sat as close to the opposite end as he could. He was shy, but so was I. Even though I was demanding in my emails I still couldn't take charge and seduce "a man".

We sat there and talked some. I surprised myself by opening up to him a little and telling how the man with the 10" cock busted my cherry. And he told a little about what he'd done with his first man on man encounter. As he talked I played a little game with him and I turned and spread my legs so he could have full view of my already rock hard cock. I was dripping with pre-cum as well, I could feel it between my legs and running down to my ass. After a few minutes I could tell he was not going to make the first move. So I summoned up my gurl courage and slid over next to him, I felt so weird doing this and as I began rubbing his body I thought to myself I can't believe I'm doing this! Me of all people dressed like a woman and playing with another a man... But feeling another man's body under this sexy nighty sent me over the edge, I think I understood why these men liked me so much.

I leaned in closer and began nibbling on his ear and kissing his neck. Then I felt him put his hand on my thigh and he squeeze it and rub it. I let him know I liked that by whispering to him how nice that felt, I told him to feel up higher which he did. He would only let the back of his hand touch my cock and balls while he rubbed the inside if my thigh. My hand made its way down his body and onto his panty covered cock which was now hard and I could feel a large wet spot on his panties. I told him how hard he it was because I was so sexy and I was making him feel something he didn't know he had. I thought for second he was about to kiss me but he didn't, I really didn't know if wanted another man kissing me or not anyway but I'd let him if he'd done it.

I kissed his neck and ears a little more then I started working my way down his body. When I got to his cock I left the panties over it and kissed it. I started sucking his cock through his panties, that was really hot for me, I could taste the pre-cum on the panties. Kissing and sucking a cock through panties was one of the hottest things I'd ever done, it made my cock jump. I finally pulled it out and in one gulp I took the whole cock in mouth. He wasn't near as big as my first one but it was nice, big enough to feel and now hard enough to fuck me I started getting really excited. I made the suggestion we head to the bed and off we went.

We laid side by side for a few minutes me playing with his body and him still playing with my leg. I was dying for him to take the lead and suddenly he turned over and laid on top of me, he began playing with big fake tits like they were real, he squeezed and sucked them and even wiggled them up and down and side to side. This drove me absolutely nuts, it almost felt like my tits were real and I could feel it and now this man was playing with them like they were real. And having him lay on top of me I could feel his cock down around my thighs and the wetness was still pouring out of him as it was me. I could literally feel it soaking my hose and running between my legs. I didn't let him finish, I moved him over and I began playing with his body. I kissed his neck, ears and chest, I sucked his tits through the lace of the nighty, I got so hot doing this I was out of control and he loved as much. I worked my way down where I found his cock again and began sucking him again. I was torn between making him cum in mouth or letting him fuck me. I wanted both badly. But after I'd made myself so horny I raised up licking his cock as I did and asked him if he'd fuck me with this.

He said yes! He asked how I wanted it so I just turned over on my back and raised my legs and said like this. He got on his knee between my legs and held them. He tried to get in but I'm tight and even though I had my own lube running into this spot I needed more. Then he started trying to get in again and all of a sudden I felt the most wonderful thing, the head of cock slid in me! He stopped making sure not to hurt me. To me, there is nothing like feeling a cock slid in you for the first time. I was waiting for the pain like my first time but because he wasn't as big as the first one I felt very little pain if any and I said give it to me baby! And he did shoving it all in, I let out this long loud moan followed by oh my god that feels good! It seemed I had no control of my body or what I said. I'm normally very quiet not much moaning or anything but now I was moaning and talking saying crazy stuff, not like me at all but dressing had changed me into something I didn't know I could be. He started fucking me and I looked into his eyes and seen he loved the way I felt also. I'd made him hard enough to fuck me and that meant I was a hot sexy gurl and he liked me.

I felt so many different emotions as he fucked me. I remember thinking now I have my second cock in me and it feels so good. I also thought if I'd knew this would feel this good I'd done this a long time ago. I kept watching his face and seeing the pleasure my body was giving him and he was looking at my face then my tits. I loved it. Then without any warning I felt like I was going to cum, I could believe it my cock had barely been touched. I didn't think this was even possible but I could feel it, it felt so good. My whole body was trembling, I just knew I was going to cum, I kept thinking my god what is this doing to me, but then he started breathing really fast, his fucking got faster and short and he started cuming and I mean hard, he started ramming his cock in me as hard and deep as it would go grunting and saying shit over and over, I said oh yes baby give to me. I could feel his cock jerking and I could even feel his cum inside me.

And now I'd made a man cum inside me and it was better than I'd hoped it would be. I felt so much like a woman, it'd changed me that much. When he finished cuming his body was shaking from weakness and he fell down on top and laid there not moving and trying to catch his breath. I kept my legs high so his cock would stay in me. I rubbed and scratched his back with my long nails. As he laid there his cock got soft and little and it came out. I could feel his cum start running out me as well. I was so horny and hard; he could still feel it. He raised up and said I want to make you cum like that and he sat between my legs and began stroking my cock. I felt so good knowing he wanted me to cum as well but he wasn't doing it right. I took my cock and told him to watch and I began to masturbated for him putting on a really good show. He was playing with balls as I jacked off with one hand and the other on my big tit, with all that had happened it wasn't long before I was cuming very hard, my body shook and jerked all over. It was amazing! He came back a few times after this, he actually became the first man I fucked which was something I never thought I'd do. I'll tell you about that later as well.

After he had gone all I could think of was how I nearly came while being fucked and my cock not being touched. I had so many emotions over this. I began to worry about how much this all was changing me. But the one thing I kept thinking about was how good that felt and the higher state of excitement it had put me into. I'd never been like that before it was like I was a different person. So I decided I didn't care how much this changed me or what I had to do, I wanted to cum by being fucked only. This is the one thing that I believe may have changed me nearly as much as dressing if not more. I think It along with saying yes to everything made me do things I'd never done otherwise. It made me say yes to everything and anybody. It made me such a freak but I didn't care. I'll tell you now, I was finally able to cum like this but it wasn't for a while, I done a lot of things to get there. It made me find new things to try.

CutieToni
CutieToni
19 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousover 7 years ago
wonderful story

This is an excellent 2nd chapter to your first story. I hope it was true like the first one was. I too am a CD and like in your story I love being with another CD. I've also progressed to being totally naked with other men -- no women's clothes at all. It may seem to you that being fully naked with another man is "gay" but you should really try it. Since you've already sucked a cock and gotten fucked (at least twice) being in bed with another man and having hot gay sex is actually wonderful. I look forward to reading your 3rd story and how you have progressed in your sexual desires.

AnonymousAnonymousabout 8 years ago
Thank you!

That was lovely sweetie! I wish I was there!

AnonymousAnonymousabout 8 years ago
Loved it

Your stories and the way you told them was amazing which also got me so turned on I couldn't help but play with myself

Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
How Crossdressing Changed My Life 4 years ago I would have never guessed I'd be the woman I am.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
The Sweet Taste of Honey A young man's fantasies transform into reality.in Transgender & Crossdressers
The Seduction of Peter Young man is seduced by an older woman who shares his fetish.in Transgender & Crossdressers
More Stories