Little did I know what was coming on my 16th birthday…
Cheryl, my 19 year old sister, my 37 year old mother and I were eating supper like any normal Thursday night. It was the one night each week when Mom insisted we all eat together. She and Dad had divorced when I was 4. I never did know what the split was about, but Mom had sworn off men. “Dates” she went on were always with women. Cheryl dated a guy for a while, but now was openly gay, and Mom did not seem to have a problem with it. Friday night, Mom was going out with a girlfriend of hers. Cheryl was going to have a friend over. They had been talking about it through most of the dinner.
“Happy Birthday Son” Mom commented when I had finished devouring my food. “What are your plans for tomorrow after school?”
“Oh I don’t know. I’ll probably just stay in my room and read a book or something. I wouldn’t want to be a pain to Cheryl and Sandy.”
That elicited a giggle out of Cheryl. She and I didn’t really get along that well. We tolerated each other, but generally considered each other as a pain.
After a long pause, Mom asked, “Why don’t you go out on a date? You are old enough now…” Another long pause then “Are you gay like your sister and I?”
Cheryl choked, spraying the water she was drinking all over the table.
“Oh Mom! You mean guy on guy? That’s gross!” I exclaimed. “I don’t mind lesbians, I would be one too if I was born with a vagina. But the idea of… yuck! Cocks are just gross! That is just wrong! Ewwww!”
“Okay, okay. I get the idea. The envelope on the coffee table has your birthday present in it.”
When Cheryl had quit laughing, she informed me that even she had got had got a present for me. It was still in her bedroom, and was not wrapped yet. I was welcome to come and get it if I wanted so that she wouldn’t have to wrap it. Not really knowing what to expect, I followed her upstairs to her room. Surely I wouldn’t be interested in anything SHE got for me…
“There it is,” Cheryl declared with a flourish toward her bed. My cock jumped at the sight of her blue satin nightgown. Fear soon took over when she said “It is yours now. I know you have worn it before. It has stains from you cumming on it.”
I was busted now and I knew it. Surely I was going to be in big trouble.
“Go ahead put it on” she whispered in my ear. I want to see what it looks like on you.
“You mean you’re not mad at me? How long have you known?”
“No silly. I’m not mad. I’ve known for a while. Go ahead and put on your nightie. I will turn my back if you want, but you have to take everything else off before you put it on.”
Still unsure of how this was all going to turn out, I did as she asked. I was pretty nervous, but exited at the same time. Cheryl added to my excitement when she removed her top and bra with her back to me. When she turned to face me, all I could do was stare at my sister wearing only a mini skirt, nylon stockings, and 4 inch heels. Her 34B’s were just perfect as far as I was concerned.
“Have you ever seen a live girl naked?” she asked. The answer was no, but she did not wait for it. “Oh look! Your cock is hard sticking up in your nightie. Let me fix that for you.”
She pulled up the bottom of the nightgown that hung just below my knees and exposed my now throbbing member. She wrapped her fingers around it and slowly started pumping it, then kissed the pre-cum oozing tip. She took the head into her mouth and I came almost immediately, pulling away from her face in surprise and embarrassment. In the process, I managed to squirt cum in her mouth and all over her face.
“You cum quick.” Cheryl remarked. “I’ll be back with a towel to clean up with.”
“I’m so sorry,” I mumbled when she returned. I had taken the nightgown off and was sitting on her bed in my briefs. As was usually the case when I came while crossdressing, the first thing I wanted to do was to get out of the clothing I had dressed in.
“It’s okay,” she soothed. “But if you are going to be my sister you cannot wear those,” indicating my shorts. “You can wear panties or whatever else you like as long as you ask first and do not cum in them.” Rubbing my leg, she said “Go ahead and get dressed as my brother for now, but we will do more later. I’m sure you don’t want Mom finding out about this.”
She was right. I couldn’t even imagine what would happen if Mom found out what we had just done. Cheryl kissed my cheek as I stood up to leave, saying “Tomorrow I will teach you how to return the favor.”
I left with my mind going in circles. My relationship with my sister whom I did not get along with very well, had changed forever.
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