My Terrific Sister

My sister and I were always close. She knew I was effeminate by nature. So she wasn’t surprised when I asked her to help me crossdress. She was happy to help. She taught me to apply makeup and choose women’s clothing that aided me in my feminine appearance.

When I undressed in front of her to try on the panties. My sister saw my penis. She said I had a nice size penis. My penis is 7 inches and I have rather large balls.

She took my penis in her hand feeling it almost like an examination. My penis got hard at her touch.

“Oh., this will not do.” She said. “Men are insecure about their cocks. You cannot get hard when you’re with a man.”

She began a stroking motion as she continued talking holding my cock.
“You have a nice cock. It’s thick and long. It’s too bad you’re into men. There is a lot of pussies out there that would have liked this cock.”

My cock was so hard from her gentle strokes it almost hurt. My sister continued. “We will need to get this to go down so we can tuck it away.”

Her stroking felt so good. I was feeling a rush of horny excitement. So much so that when I tried to speak the words were caught in my throat unable to come out.

My sister released my cock. She took off her pants and panties. I stood there watching her admittedly excited as I had never saw a pussy before.

She took my hand and led me to the couch. She laid back with her legs spread and pulled me on top of her. I felt her hand as she worked the head of my cock into her pussy.

Once I entered her. I automatically began stroking in and out. I felt her back up against me as she was trying to gobble every inch in her pussy.

She let out moans as she continued to thrust upward against me. I had never felt my cock inside a pussy. It felt good.
She continued grinding and thrusting I felt her hands on my ass as she pulled me in close. I could feel her pussy spasm around my cock. This sensation instantly made me cum. She held my ass so tightly grinding against me. I could not of pulled out if I wanted to.

She continue grinding against me, holding my ass as if she was trying to drain every drop of my cum from me.

We lay there together for a few more seconds. And then she signal me to get off of her. I stood up next to the couch looking at her is she lay there with her legs spread. She motion for me to hand her the panties from the floor. I gave them to her but instead of putting them on, she used them to wipe up my cum that was draining from her pussy.

She got up and went into the bathroom.
A few seconds later, she returned.
“Wow little brother that was good.”
Now let’s get back to getting you ready to find yourself a cock.”

I just stood there speechless over what had just happened. She knelt down in front of me and began examining my cock again. It was still semi hard. She fondled it and told me it would still be difficult to tuck it away.

She felt my balls. “I think little brother, if we keep these balls empty and then restrict the circulation to them and that will shrink your cock. We can also bind it, restricting its blood flow and tuck it away. We are definitely wanting to keep this limp when you are being a man’s woman.”

“Well , that’s enough for today. We can feminize you some more tomorrow.”

The next morning right after breakfast my sister said she wanted to work on my conversion again . I followed her into the living room. She told me to take off all of my clothes, so I did.

As I stood there, naked, in front of her, my cock again started getting hard. My sister took a hold of it and again giving it a gentle, stroking motion.

“I was afraid this might happen.” She said. We will have to drain your balls again. She led me to the couch. She took off her pants and panties, and laid on the couch as she did the day before.
I got between her legs and inserted my cock. We fucked much as we did the previous day.

After we had finished, my sister returned to feminizing me. She applied my makeup and lipstick. She was only wearing a T-shirt as she never put her pants or panties back on. Likewise, she also left me naked from the waist down. Every so often, she would gently run her hand over my cock.

She put out a bra. She said it was a padded push-up bra that would be perfect for me. She put it on me.

She had me look in the mirror from the waist up I was looking very feminine.
Then she said. “Oh little brother I just realized you have never seen my titties.”

My sister, then pulled off her T-shirt, revealing her breast to me. As I looked on her naked form standing in front of me, I could not help but get another erection.

She saw that right away. “Oh I see we have another problem.” She said “well we better take care of it.”

She took my hand and led me to the couch again, and as before she laid down and spread her legs. As before we vigorously fucked until my balls were empty.

After that, my sister continued to walk around, totally naked. She kept talking about binding my penis, so it could not get hard and tucking it away, so I could be with men. But never made any attempt to do so.

It wasn’t long before my cock was hard again. Again, she took me to the couch and we fucked until she drained my balls, and my cock went limp.

She asked me if seeing her nakedness was getting me excited? I admitted to her that it was. She told me that would not do if I intended to be in the female role with a man. She dressed me completely from head to toe as a woman. But then she herself remains naked. She said it was best I get used to seeing a naked woman, so it would not be so arousing to me.

By that evening, I found myself with another erection, and as always my sister saw it right away. This time she led me back to the couch, and as we started fucking. She told me to think about cock.

Instead of thrusting against me, as she done the previous times, we fucked. This time she laid still. As I went in and out of her pussy, she talked about cocks.
She talked about different shapes of cocks, different colors. She told me too think about how wonderful it would be to suck a cock. To be a woman for a man.

As she felt my cock swell. She had me say out loud I love cock I want to be a woman for a man.
She continued this until I again emptied my balls in her pussy.

I didn’t know it then, but that was beginning of my training. For the next several months I fucked my sister as she talked about cock.

One day my sister got me looking rather pretty. She had a surprise for me. That night a man came to our door she let him inside then she told me I was to suck his cock.

The man pulled his cock out, and as instructed, I began sucking him. My sister was giving me instruction and encouraging me as I performed the task after he finally came in I swallowed his load he left.

My sister said she was proud of me as she watched my cock and it stayed limp during the process. I think it probably had more to do with her constantly draining of my balls.

She eventually taught me how to tuck everything away. And keep my cock shrinking and my balls small. I started seeing more and more men. My sister eventually found a steady boyfriend.

So now I am just her gay brother. We don’t have sex anymore. But I will have to admit for a while there I wanted to go straight. But my sister put me back on the correct path as she always said being a sissy bottom was natural for me.