My irritation subsided when I saw the insistent look in my mom’s eyes. Recalling how she asked me to put myself in her hands while we were here, and how I agreed to do that, I nodded my head and let her continue.
“Bobby,” she continued, “your Aunt Brenda knows everything now. About us, all about your panty fetish, and the strap on….. everything. I was completely honest with her. So there’s no reason for you to feel uncomfortable. As you can see, she doesn’t think any less of you for any of it.” I glanced at Aunt Brenda as she sat there quietly.
“Anyway,” she added, “we thought the two of us could help you understand and become more knowledgeable and comfortable with ‘girl things’. We came up with some ideas and that’s why we’re here. So, like I asked you in the car, can you trust me and put yourself in my hands for a while?”
I looked at my aunt again. She smiled softly and nodded her head up and down, assuring me it was the right thing to do to say ‘yes’. I also noticed she was holding my mom’s hand now as if this was a pivotal moment in history, and they were giving each other emotional support.
“Sure, mom,” I answered, “of course I will.”
The look of relief on my mom’s face was evident. Her smile came back and I felt the anxiety around us melt away. She squeezed my hand and then let go of it. “Good, sweetheart, you won’t regret it.”
With that, she raised her hands and began to unbutton my shirt while I stood in front of them. As she went from one button to another, she explained. “Sweetheart, before we start, I want to help you live out one of your fantasies.” When she got to the last button, she opened up my shirt and lowered her hands. I looked at my aunt, and her eyes were glued to my chest, taking in the sight of her nephew in a bra.
I felt the sharp sting of embarrassment flow all over my body, practically blistering my face. It was like a hundred sun lamps were focused on my cheeks and I found myself taking short choppy breaths to keep up with my racing heart.
My mother noticed my condition. “Relax, sweetheart.” Mom urged, sitting next to my aunt. “Take a deep breath and settle down. We still have a lot more to show her and I don’t want you hyperventilating on me.”
My aunt’s eyes were staring at my bra and I could tell she now had a hundred questions in her head about me. For example, if I was wearing a bra, what was I wearing under my pants? But, the tingly excitement in my crotch was overpowering and I relished the way her gaze made me feel on display. I don’t know if I was more excited for her to see me in my sister’s bra, or the fact that I was becoming desperately eager for her to see me in my sister’s panties, too.
Aunt Brenda stood up and laid her hands on my chest, cupping my tiny man boobs in her hands and running her fingers lightly over the material. “This is a good look for you, Bobby.” She said.
“You know, what a girl wears under her clothes tells a lot about her.” She added, as she toyed with the plain fabric of the bra. “I’m thinking you might like the feel of silk or nylon against your skin; something soft and slinky sliding across your body to give you that ‘grown-up’ girl feeling. Maybe some nice, soft camisoles? What do you think Sherri?”
My mom agreed. “I promised I would buy him his own lingerie. I think some silky camisoles would be a good addition to our shopping list.”
“Do you like dressing like this?” My aunt asked me, running her hands over my chest and stopping to cover my bra cups with her hands. “It’s not that uncommon, Bobby.” She added. “Many men and boys are drawn to female clothing, you know. And, it’s not because they’re gay or anything like that, it’s because they admire the femininity of a female and want to have that for them selves. Many boys grow up with a loving mom, like you did, and it’s completely normal for them to want to feel feminine at times.”
My aunt’s words struck a chord with me. Mom could see I was thinking about what Aunt Brenda said.
“I told him he could dress as a girl at home, if he wanted to.” Mom added, reaching for my hand and holding it lightly. “I’m sure his sister’s not going to mind, and I know his dad is going to be fine with it.”
“That’s a wonderful start,” my aunt replied, “being able to be yourself at home is the first step in understanding all your feelings, both male and female. I’ll tell you what, Bobby,” my aunt continued, “if you ever decide you want to experience full femininity, I hope you’ll let me help. We can do your nails here, your hair and eyebrows….. show you some things about make up. Your mom and I can teach you about things like hosiery and so many things girl’s need to know. There’s no pressure,” she added, “I’m just offering.”
My mother’s thumb was gently caressing my hand as she held it. “That sounds like a nice offer, sweetheart. I hope you’ll think about accepting it.” Mom said, then followed with, “Why don’t you help him off with his shirt?”
As my aunt nodded, she reached up and slipped the shirt from my shoulders and down my arms. As it came off, she folded it carefully and set it on the side of the bed and then sat down next to my mom. After my aunt was seated, mom’s hands reached up to my waist and unbuckled my belt. She smiled smugly and turned to my aunt as her fingers moved to the snap of my pants and said, “You should have seen the look on his sister’s face this morning when I stood him up and undressed him in front of her. It was priceless.”
I didn’t feel it until now, maybe because I was numb by then, but, my cock was throbbing, and as mom’s fingers searched for the zipper, I felt her pressing against it. My mind screamed “Oh fuck! She’s really going to do it! She’s going to pull my pants down and let my aunt see me wearing my sister’s panties!”
Mom continued her narration to my aunt, telling her in lurid detail how she exposed me to Linda in the kitchen; taking her time to explain every facet of what happened. With every word, the level of my excitement and desire grew. When she described to Aunt Brenda how the outline of my cock looked as it pushed against my sister’s pink bikini panties and how obvious it was that I was erect, I couldn’t stop myself from shuttering. “Easy, sweetheart.” Mom said. “Calm down. I don’t want you shooting off in your pants. We don’t want you getting messy down here, now do we?”
Once mother got my pants unzipped, she put her hands on my hips and pulled me a few inched closer to them. Then, without warning, she pushed my pants down and let them fall around my ankles.
Not a word was spoken as my aunt studied me. I could see her eyes looking closely, taking in the way my panties bulged out and straining to see my cock and balls through the almost transparent material. Every second I stood there in the silence felt like an hour. My heart thumped in my chest as I endured the rapture of this glorious torture.
While my aunt inspected me with her eyes, I felt my mom’s hand on my bottom. She was gently caressing me, her fingers lightly tracing along the crease of my cheeks, down to where my balls were safely nestled in the girly panties my sister dressed me in.
“We’re almost there, Bobby.” Mom said softly as she caressed my bottom. “Let her look at you for a few minutes and then we’ll go all the way and let her see the rest.”
I knew the view my aunt and mom had must have been lewd and graphic, to say the least. I waited patiently while my mother continued to recount the story of how she undressed me and pulled my panties down in front of my sister. As she spoke, her free hand found its way to the front of my panties where she started to feel me up, idly rubbing and fondling my cock as it throbbed in response. Through all of this, it seemed like every other sentence out of my mom’s mouth contained the words “his panties”. And every time I heard it, it was like someone sucked the breath out of my lungs and I got closer and closer to a point where I knew a spontaneous ejaculation was imminent.
I stood mutely in front of them while mom told her how I thanked my sister for letting me wear her lingerie, and how I told my sister it was okay if she touched my cock while I stood naked in front of her. Each and every minute my mom drew this out, my heart beat harder and my need to be fully exposed to my aunt churned inside me. I silently prayed for her to get on with it. She knew damn well what she was doing to me — and I think she was enjoying it.
Finally, mom finished the story. “And you didn’t even let him cum?” My aunt asked. Both she and my mom laughed back and forth as my mom shook her head and answered “No, he hasn’t cum all day!”
After their laughter died down, mom asked Aunt Brenda if she was ready to see me naked.
“Sherri, would you mind if I touched him for a few minutes, first?” Aunt Brenda asked.
“Of course,” mom answered, “help yourself, but, be careful and don’t jiggle him around too much. He’s already been complaining that he needs to cum.”
“Well, we should really let the boy have his cum, Sherri.” My aunt replied, as her hand moved extra cautiously toward the front of my panties. Mom reached for her hand and guided it directly to my bulge. “You don’t have to be that careful, Brenda,” mom said, emphasizing the word ‘that’. “I don’t think he’s going to explode just by being touched. Besides, he’s probably so numb by now, he’ll never even feel it.”
Mom gave a little snicker and glanced up at me. “Aaahhh.” I moaned as my aunt’s hand pressed against my panty encased rod. I needed to cum so bad. My mom knew exactly how I would react when she told my aunt she could touch me. “Please don’t get carried away now, Bobby. You’ll spoil one of our little surprises if you do.” Mom warned me.
It was curious how my aunt asked my mom if she could touch me, rather than directly asking me. And it was just as curious that my mom answered her, not even giving me a say in the matter. Not that I would have said ‘no’, mind you.
My aunt’s hands were magical. She did a very thorough job of feeling me through my panties by applying a mixture of soft and firm pressure. She squeezed and felt me thoroughly, including my full nuts. Finally drawing her hands back, Aunt Brenda turned to my mom. “You’re so lucky, Sherri.” She said jealously. “And you have him trained so well already.”
“Sweetheart,” mom said to me, “I think your aunt would like to see your penis now. Do you want to slip your panties down and expose yourself, or, would you like it more if I did it for you?”
I didn’t answer her, but it wasn’t because I couldn’t speak. Honestly, I was meticulously considering mom’s question.