Erica's First Experience

ERICA'S FIRST EXPERIENCE

I have been chatting with a member of Literotica. He has been asking me questions, and I am only too happy to answer. He asked what was my first experience and how was it? I thought that, that would be a great story. Everyone who reads my stories will now know how it all began.

My penis and testicles never developed and I developed breast. My penis is about three quarters of an inch and never gets erect, and I do have to sit to piss, and my testicles are very small. I refer to my testicles as my little raisins. I can get hit or slapped on my raisins and I feel no pain. My breasts are a robust 36C.

When I got out on my own, I separated myself from childhood friends and started to dress girly all the time. I made new friends. The one thing that was lacking was the sexual experience with a man.

I was shopping one day, and on my way out of the grocery I picked up a local newspaper, Gambit. There was an ad for an adult dating site. I went through everything and got myself set up on the site.

I had several responses to my ad. I read through all the responses and I wanted to be careful with my first selection. I was very reluctant to respond, but I did. I needed to feel what a woman felt sexually with a man.

The first ad I responded to was to someone who did not live very far from me. He wanted me to meet him at his apartment. He explained that he did not drive and he lived alone. His reason for not driving was that he was diabetic and he had the left leg below the knee amputated.

I dressed in my usual attire, short skirt, button down blouse, garter belt and stockings, bra and panties. I wore a modest pair of 3-inch heels. I am tall as it is, and the heels make me taller.

I got to his apartment and parked a couple doors away. My heart was pounding and my throat was getting dry. I told myself this is what you wanted, now go get it.

I turned off the car engine, grabbed my purse and walked to his door. One of his neighbors was sitting out, smiled at me and said hi, I smiled back and said hi to him. I reached for the doorbell, and the neighbor said, "Chuck is a lucky guy!"

I rang the doorbell, the door opened, and there was a middle-aged man on crutches. He actually was an amputee. He lived in this little studio apartment the only privacy was a door for the bathroom. I walked in and he motioned to the couch for me to sit.

He hobbled over and sat next to me. We had about a foot distance between us. He said, "I'm Chuck" and I replied, "I'm Erica."

He said, "it is a real pleasure to meet you, Erica."

We talked, and the more we talked, the more I felt sorry for the guy.

As I stated previously, he was in this tiny studio apartment. He said that his brother picks he up once a week for grocery shopping. He also said that he walks to a little pond on the property and sits on a bench and watches the ducks. He also watches a lot of television. Other than that, that's his whole life.

We talked for a few minutes and Chuck asked, "would you like a beer?" I said, "that would be nice." He got on his crutches and hobbled to the refrigerator for the beers. I got up and said, "let me help you with that." He opened the door to the refrigerator and grabbed two beers.

I took the beers from him and we got back to the sofa and Chuck awkwardly fell backwards onto the sofa. I sat beside him and I opened the beers and gave one to Chuck.

We talked for at least two hours. I was not interested in doing anything too fast. With this being my first time. I was feeling more and more comfortable the more we talked.

Chuck was wearing a T-shirt and very lose fitting pants. I could tell he had no under ware. That made me feel a bit uncomfortable, my first time experience. I never saw a cock in real life, now I think I will experience my first real cock.

Chuck moved closer to me, very little separation. My heart pounding again. He put his hand on my leg, looked into my eyes and asked, "do you mind?" Nervously, I said, "no". He rubbed up and down my leg and got his hand under my skirt. He had a smile a mile long.

With the other hand, he pulled down those lose fitting shorts. Wow, his cock was long and thick. I said to him, "I am glad the diabetes did not affect your cock.

He got his hand up to my panties and was rubbing my little clitty. He moved closer and started to kiss me. Another new experience, I never French kissed a man before. Chuck was really making me feel like the female I wanted to be.

I reached down and grabbed his cock. It took seconds for him to get hard. I thought to myself, it's time to give my first blow job.

I worked my way out of his embrace, bent over, and I just licked the head of his cock. I licked and licked like a lollypop. I was quite surprised, Chuck's cock tasted very pleasant. There was a hint of pee, but that was to be expected.

Now it is time to dive into the deep end. I put all of Chuck's cock in my mouth and I gave my very first blow job. I was cock sucking and ball licking and sucking. What an experience to have. I felt euphoric, I felt like the woman that I always wanted to be.

I just kept sucking and licking, and suddenly Chuck lets out a loud grown and I feel this hot load of cum shooting in my mouth. My dilemma, do I swallow or not. I pulled away from Chuck, and looked at him in the eyes, I opened my mouth to show him the cum.

Chuck asked, "do you need to spit?" Without hesitation, seconds later, I opened my mouth to show Chuck that his cum was devoured. We sat back and started talking about how wonderful our experience was.

Quiet settled in for about a half hour. I was debating with myself. Should I leave, or wait until I am asked to leave?

No need for the unilateral debate, Chuck reached over and unbuttoned my blouse and pulled it open. He was rubbing and squeezing my titties in my bra. He pushed my blouse off of my shoulders and unfastened my bra. He pulled it down and started to suck on my titties like a newborn child. He really gave my titties a good work out

He sucked so hard, my nipples were beginning to hurt, but hurt in a good way.

He turned me so that my back was up against the arm rest. He pulled my skirt up to my waist and positioned one leg on the back of the sofa and the other leg on the coffee table. I am in the most vulnerable position that I can be in.

He wiggled my little thong panties down to my knees. I took my leg from the coffee table and removed my panties completely. Chuck saw how moist my little clitty was. He said, "you sure are wet!" I replied, "you were not the only one to cum!"

He buried his head between my legs and started licking all the cum off. Then he gently took my little clitty and raisons into his mouth and he was licking them thoroughly. He wanted to stick his finger into my sissy-pussy, but he found my butt plug.

He never missed a beat and, he kept licking and playing with my butt plug. Chuck eventually pulled out my butt plug and got a finger inside of me, then two fingers and then three. Chuck had my entire body trembling.

He repositioned himself, hard as a rock again, and said, "I want to fuck that sweet ass!"

I was now in a position, that I wanted that cock inside my sissy-pussy more than anything in the world.

I pulled my legs back and gave Chuck easy access, I said, "please go slow."

He got to the point where I could feel the head of his cock up against my sissy-pussy. I reached down and pulled myself open. Chuck slowly slid his cock inside of me.

It was such a great feeling knowing that I had a man's cock buried in my sissy-pussy.

He leaned forward and was on top of me. His arms were under me and holding tight. He started out with a slow motion and he gradually got a good rhythm going. I could feel his every stroke inside of me. I asked if he wanted to change positions. He said, "no, I am going too good to stop."

Chuck just kept humping me and humping me. I could feel his cock grow a bit, and with an even louder sound, I felt a load of hot cum shoot into my sissy- pussy.

Chuck just laid on top of me. He lifted his head and gave me a long deep kiss. Chuck said, "it has been so long since I have had actual sex and it felt great. He asked if I would come back again?"

I told Chuck that it was very enjoyable for me too and that I would be back again. Chuck just laid on top of me for a few more minutes. He eventually got off of me and sat up. I was still on my back.

I was still laying in a spread-eagle position. Chuck reached for my leg on the back of the sofa and rested it on his leg. He began to rub my leg again.

I could now feel Chuck's cum dripping out. I asked Chuck to hand me my butt plug and he did. I told Chuck I did not want to ruin his sofa, and I wanted to keep his man juice inside of me for a little longer.

I told Chuck that I had a confession to make.

Chuck said, "what kind of a confession do you have to make?"

I said, "Chuckie, this was my very first time with a man, I have never experienced any kind of sex with a man before. I have to say, the entire experience was beyond my wildest dreams."

Chuck said, "You could have fooled me. You seemed to be quite experienced. I was only too glad to help you with your first encounter with a man. I hope that we can make this happen often."

I said to Chuck, "I think that this will be at least a weekly thing. You made me feel like the woman I always dreamed of being."

I finally sat up straight and decided to get dresses. I put my panties back on, pulled down my skirt to the correct fit, put my bra back on and buttoned my blouse. I asked Chuck if I could use the bathroom to piss and brush my hair.

Chuck said, "sure you can use the bathroom, but promise that you keep the door open."

Chuck's line of sight was right on the toilet.

Wow, Chuck wanted to see me piss. I got up and walked to the bathroom, turned so that I could sit. I pulled up my skirt and lowered my panties, sat, and began pissing. I finished pissing, wiped off and pulled my panties up and lowered my skirt. I got my brush from my purse and brushed my hair. I went back to sit with Chuck.

I sat down, Chuck immediately put his hand on my leg and asked, "when will I see you again?"

I said, "maybe next week we can work out something."

We exchanged telephone numbers. We had one more deep, wet kiss.

I said, "I will be going now. Please, let's stay in touch." I told Chuck there was no need for him to get up, I could find my way to the door. I got up, grabbed my purse, leaned in and gave Chuck another kiss. As we kissed, Chuck's hand went up my skirt and grabbed my little raisins and gave them a nice squeeze.

Chuck said, "they feel so nice and soft."

I thanked Chuck.

I dreamed often about sucking cocks and being fucked. For some reason the thought of kissing a man was repulsive. Kissing Chuck, I realized that kissing a man was as great as the sucking and fucking.

I got to the door, stopped, and looked back at Chuck, and said, "I will see you soon." Then I blew him a kiss. I opened the door, walked out and closed the door behind me. I walked toward my car, and Chuck's neighbor, who I saw when I got there was sitting out. I walked toward him.

The neighbor said, "did you take care of my boy?"

I said, "why does that concern you?"

He said, "Chuck is a good guy and got dealt a bad hand with the diabetes, he really deserved better."

I asked, "do you know Chuck well?"

He said, "well enough, on several occasions we have pizza and beer together and watch ball games. Chuck loves sports."

I said, I am glad to see that someone checks in on him."

He said, "that horrible brother of his don't give a damn. I am surprised that he even takes him to the grocery." I must say, "Chuck has got real good taste inviting you over."

He said, "how about joining me for a drink? I could use a little company."

I thought to myself, you took care of one, now you can do another and turn slutty in one afternoon. I agreed.

He got up from his chair, opened the door for me, and I walked into his apartment. He followed right behind me. He motioned to a chair for me to sit. I sat down, crossed my legs and he sat beside me in an adjoining chair.

He said "beer is the only alcohol to offer."

I said, "a beer would be fine."

He got up and walked into the kitchen, grabbed two beers from the fridge, opened them, gave me one and sat back down.

I said, "my name is Erica. What's yours?"

He said, my name is James, but everyone calls me Jimmy."

I said, "Jimmy, your apartment is bigger than Chucks. How big is it?"

Jimmy said, you are talking about the apartment?"

I said, "yes, the apartment."

He said, it's two bedrooms, my son on occasion comes over and spends the night."

I asked, "how old is your son?"

Jimmy said, "he is 20, and going to college."

I asked, "how often does he come over?"

Jimmy said, "once, maybe twice a week."

We talked, drank our beer. The television had a basketball game on at the time. We occasionally glanced at the game and commented on it. We finished our beer and Jimmy said, "let me show you the rest of the apartment."

He really kept a clean apartment, and he had really nice furniture.

We got up, proceeded to the kitchen, I stuck my head into the bathroom. The bathroom was roomy and modern. From there he showed me the bedroom his son used. Once again, very nice, decorated and with nice furniture.

Jimmy said, "I saved the master bedroom for last."

We walked in, and I was amazed to see how nice it was, beautiful furniture and on the walls was artwork.

Jimmy said, "what do you think of my bedroom?"

I said, "this is really nice, I like it."

Jimmy moved quickly behind me and pushed me onto the bed. I was not expecting this. I thought that we would eventually end up here, but not this way.

Jimmy closed the bedroom door, pulled his pants and shirt off and stood in front of me completely nude.

He said, "I need relief now! Sit up and come close and put my dick in your mouth and take care of it!"

I was feeling a little scared, so I did as I was told. I moved in as close to Jimmy as I could. I had to pull my skirt up and open my legs so that Jimmy could move in close. I took Jimmy's cock in my mouth and began to lick and suck. Jimmy's cock was longer than Chuck's cock, but not as thick.

I could feel Jimmy harden in my mouth. He put his hands behind my head and pulled me in real close. He held my head and started to fuck my mouth. His grip was so tight, I could not pull away. Every time he went in, I could feel the tip of his cock hit the back of my throat.

As scared as I was, I was becoming more and more relaxed. Relaxed to the point, that I put my hand on my clitty and began to jill-off as my mouth was being fucked. Jimmy must have gone at it for about 10 or 15 minutes. I could feel his cock harden even more and suddenly his cum hit the back of my mouth.

He pulled out and shot more cum on my face. Wow, another first for me. He took his cock and rubbed it all over my face then he put his cock back into my mouth and I cleaned what cum was left off of his cock. I was licking the head and playing with the pee-hole. I was still jilling-off.

Jimmy stepped back and said, "I want to see you cum." He pulled up a chair, sat down and got as close as he could. He said, "pull your panties aside."

I was reluctant to do so. Jimmy did not know who I was or what was in my panties.

Jimmy said again with more emphases, pull those panties aside!!"

I was feeling really good. I felt the blow job all the way down in my clitty and I did not want to stop.

Jimmy reached in and with a bit of force pulled my panties as far over as they could go. He smiled and said, "Whoa!"

I asked if he was upset.

He replied, "no, no not at all. Please keep going."

I rubbed and rubbed, I pushed my clitty inside of me and was rubbing my little clitty head, and it was sending waves of excitement throughout my entire body. I jilled-off and finally I had a massive orgasm. So massive that I fell back on the bed and continued. I squirmed all over the bed and moaning loudly. Finaly, my juice oozed out and even a little spurt shot out.

I just laid there.

Jimmy said, "that was amazing, I never saw anyone like you. He got up and laid on top of me. My panties were still pulled to the side and I could feel him rubbing his cock on me. He looked me in the eyes, smiled and kissed me on the lips.

He said, "that was terrific. I think I enjoyed that as much as you did."

He stayed on top of me and I could feel his cock get hard. He pulled my blouse up and pulled down my bra straps and began to fondle and suck on my titties. The more he sucked and fondled the harder he got.

I said, "it seems as if you want some more."

I told Jimmy that I needed my purse, he got off of me, grabbed my purse and put my purse beside me on the bed. I opened it up and got out a bottle of lube. I pulled out my butt plug and lubed my sissy-pussy. I still had lube and Chuck's cum inside of me. I just wanted to be more accepting of Jimmy's cock.

Jimmy got back on top of me. He started to lose his erection. The second he got back on top of me and started to play with my titties, I could feel him grow. He grew to a strong and hard erection. I moved a bit, and Jimmy took my legs and put one on one shoulder and the other on another shoulder.

Jimmy moved in closer and I could feel the head of his cock at the opening of sissy-pussy. He was able to rub his cock on my gooey sissy-pussy until I could feel the head of his cock penetrate me. Jimmy started kissing my neck and complimented me on how good I smelled.

Then, he started to push his cock into my sissy-pussy slowly until he was completely inside of me. I could feel his nut sack against my ass. Jimmy just grinded himself against me for a while, he slowly pulled out and pushed back in. His motion was slowly increasing and driving me wild.

He picked up his speed and was thrusting harder and faster inside of me. Every time he thrusted in me; I could feel it all throughout my sissy-pussy. Every time he went completely inside, I would let out a loud sissy moan. The harder the thrust, the louder the moaning.

I think my moaning was getting Jimmy hotter and hotter and more turned on.

Jimmy, kept saying over and over, "do you like the feel of my big dick inside of you, do you want it harder?"

All I could do was moan, louder and louder. I think I was so loud the neighbors could hear me.

Suddenly, my entire body started to quiver, I was having my very first sissygasm. My body was quivering and shaking. As I was quivering, Jimmy lets out a loud masculine growl and I could feel his cum shoot inside by sissy-pussy.

Jimmy was slowing his thrusting down until he came to a complete stop. Jimmy just kept his relaxed body on top of me and left his cock in me. He stayed on top until his cock got soft and he pulled out. He straddled me and positioned himself so that his cock was touching my lips.

Jimmy said, open your mouth and swallow Jimmy's dick. His cock went into my mouth and I was licking him clean. Jimmy reached over and grabbed his cell phone to take a picture of me with his cock in my mouth.

I tried to break away, but Jimmy had me pinned down. He took the picture and said, "something to remember you by."

I was laying there at Jimmy's mercy, still pinned down under Jimmy with his flaccid cock still in my mouth, half way down my throat.

Jimmy got up and assured me that no one would see the picture of me with a cock in my mouth.

I am very gullible, and I believed him.

We both laid there for a while to collect ourselves. Jimmy reached down with his finger and got some of my juice off of my clitty. He put his finger to my lips and told me to lick it off.

I licked Jimmy's finger cleaned.