Dealing with It

Story Info
A tough 2 questions, life changing.
2.1k words
3.92
13.3k
1
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

This is a real story that happened to me. I know that some of you would have taken different decisions but this is what I decided to do. Excuse the poor writing since I don't have too much experience in this.

*****

I was alone once at my dads house, mom and dad were split up and I remember that one of the times that I was staying with my dad, he had a friend over. My dad had lots a friends but this particular one was going to stay a part of me for the rest of my life but I didn't know it yet.

My dad had a trip and decided to leave me and his friend at home for a few days. Nothing really out of the ordinary. My dad had remarried and lived with his new wife which left with him also.

Almost as soon as they left David, (that was his name), started by asking if I wanted to see some porn. I said hell yes.

He began putting on all kinds of porn with these great looking women and then he started to search for rougher more hardcore porn. All of a sudden he started putting these transsexual porn videos that I had never seen such a thing.

It definitely caught my attention since I was seeing this beautiful curvy woman with a stiff cock getting pumped in the ass. I have to say it really got me a bit horny but I was worried that David would notice and think I was gay.

He mentioned that it's natural for anyone to like cock, since everyone who tastes it gets addicted to it. He left it at that and we both probably went to bed horny and for myself I just went to sleep thinking about that transsexual.

The following day he came back home after he had gone out, I was in bed listening to music and he laid next to me. He said that he had gone to a strip club and came back really horny. He started saying that the women were so hot and that he wanted to fuck them so much.

I was so into what he was saying, and I thought that he was so cool for sharing and putting on porn that I really thought we were real good friends. That's when he said that a long time ago he had a friend and that they had been alone in this mountain top for several months and that to satisfy their sexual desires they jerked themselves off.

I did not know where he was going with this but then he asked "Would you jerk me off and then I will do you just to feel like we are with some girls? I mean that is what real friends do."

My heart started pounding. I didn't know what to answer and all that I did was nod a yes. He didn't wait a single second when he grabbed my hand and placed it over his bulge over his pants and underwear. He pulled his pants down and stayed in just his white underwear. He asked me softly if I could pull them so that I could touch it.

I did it like if I was possessed and did what ever he asked me to. When I pulled them down with just that hand and reached in and I was surprised at how hot and thick another persons penis could be. I had never even thought about being with a man before this.

I started to wrap my hands around his huge yet not completely erect penis and played around with it and touched his head and so, he grabbed that same hand with his big hands and made me start jerking him off.

This went on until the monster of a dick came to its full length and was so stiff it was intimidating since I was not even three times smaller than him. He started to hum in pleasure when he asked me this life changing question number one:

"Do you want to suck it and kiss it?" I was shocked! I didn't think this was going to go any further than two guys jerking themselves off.

I at first didn't say a thing. The next time he didn't ask he just told me, "Come here and suck it you bitch you know you want to right?"

I said yes. Thats when he pulled me down by pushing my shoulders and head in between his legs and thats when I got a look for the first time of the cock of this man. It was at least 8 inches cut and super thick.

He grabbed my head and positioned his head on my lips, thats when I smelled his cock and felt some pre cum on my lips, I opened my mouth to take in this mans cock and forever be a cocksucker.

I opened my mouth wide enough to take in his head and thats what he pushed into me. He explained that I should lick his head and caress it with my lips feeling every part of his head.

I followed instruction and I found my self being aroused and super nervous at what I was doing or who could come in and see me. My older brother or aunts and uncles could easily come in to the house and see what I was doing to this man.

As I was giving this man my mouth for the first time he grabbed the back of my head with his two manly hands and interlocked his fingers At that moment he pushed me down on his cock and it made me gag automatically and he didn't stop he kept ramming it in my mouth hitting the back of my thought and making me tear up. At that moment he stopped because I just started to make too much noise and he knew I started to get overwhelmed.

So he took his penis out of my mouth and just slapped me with it a bit and just rubbed it all over my face. He held and there and asked me the second most life changing question.

Do you want me to put it in your ass like the transsexuals we saw yesterday? I promise I will be gentle and I won't stick it all the way in?

My heart raced and wanted to come out of my chest. What could I say. I was already sucking this guys cock like a porn and I was horny yesterday thinking about how they stuck it to a transsexual. I said yes.

At that moment he stood up and got me on all fours and took of my shorts and underwear to my knees. He positioned himself behind me and I will never forget what he did. Before this moment he had not touched my cock and I was pretty hard now, I remember he had me bent over offering my ass and he reached down and grabbed my balls and cock for a second, that was all I needed to resist what was to come.

He spat in-between my virgin ass and slid his penis en between my cheeks to give me a clue of what was to come. That just got me even more horny. He put that big head on my asshole grabbed me tight from my hips and started pushing in.

Ahhhh that was painful. I thought I was not going to be able to take it a second more. He would just stop and hush me. Then he said, just a bit more, thats when his head went in. Awww I was so much in pain.

He said that I had taken the hardest now here came the rest of the good stuff. At that moment he grabbed me from my shoulder and hips and started pushing in the rest of his shaft. He said that he wouldn't put it all in and he kept his word. But the pulling in and out was so painful I don't know why I went on with it, maybe the thought of it being my turn at the end, or maybe because I had started to enjoy being Davids bitch.

David kept going only pushing it half way in when the main reseeded and I started to feel all filled up but the touch of his hands and the fact that I was being someones girl started to turn me on and I started to want more, and I began to push back every time he pumped and he really liked that and in turn that got me wanting more, I kept like that until I felt his pubes on my ass cheeks and his balls hitting mine. I was in heaven.

Davids squeezes my ass cheeks hard and pumps me a few times harder and that made me scream in pleasure, he was summing in my ass. Oh it felt so good to have been bred by him.

He pulled out and tossed me to the bed. I could feel his cum dripping down my ass and going to my legs. I quickly went to the bathroom a bit hurt and limping and let them out.

I jumped in the shower expecting it to be my turn and when I came out he just handed me some nylons and panties he had stolen from my mother in law and demanded that I wear them the next night when he came home. After that he just took off. I felt used and unsatisfied I was never going to be a real man after that. He turned me into a sissy for his pleasure, I could do nothing but think of his cock.

The next night came around and I don't know why but I started to put on what he asked me to. I started to put the panties and nylons on and a indescribable feeling came over my body. I ran to see if I could find some heels and a dress and I found what I was looking for. I put on makeup and lipstick, perfume and went to bed. I covered myself incase someone else came in.

I fell asleep. David woke me as he opened the door. I remember he gained and smiled and said how much like a girl I looked like. That I was beautiful. But I was not in the mood so I just turned around to go back to sleep. David was not going to have it.

He crawled in bed and grabbed me from the inside of my shoulder and pulled me back towards him ass first. He was already undressed and rubbing his hard cock between my ass and the panties it felt good but I still was not in the mood. With his hand he reached over and touched my cock in panties. He seemed not to be pleased and he reached in and tucked it in between my legs and pulled up even higher the panties to keep it in its place.

He then moved the panties away from my crack enough to slide his cock in, but I was still hurt from yesterday and I was still not in the mood, I figured that as long as I apply pressure in my ass he won't go in.

Well he grabbed his cock in one hand played me face down still in heels spread my cheeks and moved the panties. He was just bigger than me and could over power my movements to get set free. I pressed to not let it in. It popped in and made me scream

He held my mouth and pumped it into me violently. I understood that I was going to be his again. He started saying what a beautiful girl I was, that this was my present for turning myself in such a sissy and look so cute for him. That just started to make me get hard after all the struggling I wanted this.

He pumped me like that for a god 20 minutes and then flipped me around and used my ankles as earring while he plowed into me. My cock was free and flopping around.

He went on but since he was drunk by now he was more manageable so I got him on his back and I straddled him. The most incredible thing happened. He started to cum and from all that cock he gave me and my dick hitting his abdomen I came at the same time.

I left a small pool of cum while my ass was spewing in it. He grabbed me by my hps and gave me a couple more pushes and I unplugged from his cock. I felt empty inside except for his cum.

That day I became a sissy that enjoyed dressing up. He changed me from those nights on.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AlemuchomasAlemuchomasover 5 years agoAuthor
Thanks

It stays with me in memories.

AnonymousAnonymousover 6 years ago
wow

What a great story would have loved to be taken like that &have a big guy take me on regular nights tell use more

Share this Story

Similar Stories

An Unnecessary Argument I haven’t cum yet so I’m not gay.in Transgender & Crossdressers
Trained by a Succubus Ch. 01 Summoning a succubus who has a big surprise for him.in Fetish
Perfect Fit 01 A box of varied condom size, by magic are always a good fit.in Fetish
Shown Up A strong woman brings out a young man's femininity.in Transgender & Crossdressers
The Big F Surprise Ch. 01 A Virus strikes the world and leaves a young couple shocked.in Transgender & Crossdressers
More Stories