. I grew up on the outskirts of New York City. My childhood home sat across the Hudson river with a brilliant view of lower Manhattan. With that said, I rarely ever went into the city. Instead I would usually just hang out with my friends in Hoboken, drinking wine from the bag and smoking Virginia slim cigarettes.
I love my friends, and as a matter of fact, they’re the reason I became who I am now. Their encouragement and ability to see my true self never waned, and from their loving foundation I was able to blossom.
I grew up an only child in a very loving home. My parents were always very trusting of me and let me roam free as a teenager, but I never went very far. Unfortunately, my dear father had passed away when I was still in middle school and my mom had to raise me by herself. The positive side of this event was my ability to be very resourceful and economic with my decisions. My mom and I would go out to dinner every Friday evening. Always sushi. But besides that we lived a more frugal lifestyle without my father.
I say frugal with a massive grain of salt. My father was the CEO of an international non-profit for over 20 years before he passed away. The thing about non-profits is they have a tendency to accrue a lot of profit. He made well over a million a year, then the Christmas bonuses were passed around to “Clear the books”, as he would always say. He gave his entire bonus to my mother and I every year. A bonus mind you that was much larger than his actual salary. So after he died we had already accrued a lot of money. His life insurance added to it, then the dividend checks came in once a quarter. They still do as a matter of fact.
So my childhood home is still very much in our possession. It is a two story estate with an east and west wing, rolling lawn, and a massive swimming pool. It sits on the large granite boulders that scar the riverbank along the Hudson river. However, after my father passed my mom had a good mind to live more modestly, and rake in the checks as they came, constantly saving and building upon our estate. I discovered much later just how much she was able to save.
It was by the pool at the end of my senior year in high school that this story began. My two girl friends were over and we were floating around on large pool floats, talking and laughing and sipping on skinny bitches. Those were the drink of the summer as we came to learn. My mom was busy in the house reorganizing her wardrobe, so our maid was outside with us, awaiting the next order.
“Hey Chris, have you decided what to do after we graduate?” Rebecca asked.
“I would like to go to university, but I’m not sure what I would study to be honest. I don’t even know where I want to go.” I replied. But there was something timid in my response, something the girls had caught on to. There was more I had wanted to say, but I held it from slipping out.
“I want to go to school as well, somewhere fancy like Harvard or NYU. I don’t care which, as long as I meet a rich stud”, Becky giggled as she finished her drink with a slurp and we both joined her.
“What about you Chloe? What are your plans?” I was truly curious, but I also wanted to push the conversation well away from me.
“School as well, but I want to get into fashion. Parksons is the only place for me, girlies!”
We all giggled.
We’ve been besties since elementary school. I love those girls and would do anything for them. And they would do anything for me as well. I learned just how far they would be willing to help me as the summer went on. We looked after each other and our parents were all in a large friend group. The girls were my family, my sisters.
I was always underdeveloped from a male physique point of view. My puny arms never really developed from adolescence and what little facial and body hair I had was regularly removed on a weekly basis. After I was caught sneaking a skeptical bottle of liquid hair remover from China, my mom gave me a tongue lapping on how important is was to buy high quality beauty products from reputable sources. A two dollar bottle of off brand nair from Amazon didn’t make the cut. Since then she always had a well-stocked supply of hair remover she picked up from her usual salon. She would also buy rose and lavender scented body wash and shampoos in bulk that we would share.
I never liked the boys at school. All kids are mean when they are young, but boys are exceptionally harsh on feminine classmates. I avoided the boys at all costs and would hide amongst the girls in my school for protection. I didn’t know it at the time, but they had their own uses for hanging out with me. All girls like a gay best friend the saying goes. It’s just that I wasn’t gay, at least not that I was aware of. I enjoyed everything feminine from a young age, and that included girls. But whenever I would ask one out, they always thought we were just going out as friends, and the friendzone ran deep. By the time I was about to graduate, I had been on hundreds of dates. But they were the kind of dates friends had at the Fro-Yo shop or the mall. In hindsight, asking a girl out to go shopping isn’t exactly something a masculine boy would offer as a date location. But because of these moments, I was regarded as the cool boy among the girls and they always protected me from the larger football players that roamed the halls.
So there I was, in the pool with my girlies. A puny body floating on a pool noodle, no hair below my eyebrows, and smelling like freshly cut roses. I had never lost my virginity, and I was becoming less interested in losing it. In my mind, when it was the right time, it would happen. But I gave up on asking girls out and just went with the group as a good friend. Their heels would click on the dance floor while my converse sneakers squeaked. But we loved to dance, and most of the time I was envious of their high heels and the sound they produced. I wore my mothers heels when I was a little kid and loved how they propped me up and the sound of the clicks on the marble floor. But I haven’t done that for many years now. Now that I think of it, I haven’t done a lot of things like that in many years, and I really did miss it.
“You know Chris, maybe this summer could be an opportunity for you”, Chloe said with a bit hesitation. She looked at Rebecca and they both smiled toward each other.
“How do you mean? I’ve already started applying to the schools, and I’ve even heard back from a few. What more could I be doing this summer other than this?” my reply was earnest. What more could I possibly accomplish during the summer between high school and university?
Becky spoke up this time, but with more confidence. “Well, how do you plan on living the rest of your life Chris? Just hanging out with the girls, waiting for an opportunity to get with one?” She bit her lip. “Honey, if you were to get with a girl, it would have happened by now. And no offence, we love you, but most women are more interested in a more masculine man. You’re cute, but… well are you sure this is how you want to live your life?”
“What’s wrong with how I am? I’m comfortable with my body most of the time, and eventually I’ll meet a girl that likes me for me.”
“Okay, okay, fair enough. Maybe it’s time we have another round.” Chloe raised her hand toward Martha the maid and had her bring out another round of drinks. The sun was on it’s way down and the lights around the house and pool lit up. When the drinks came out, we got out of the pool and sat in the teak layout chairs on the pool deck. We clinked glasses to a perfect summer and squealed with joy. But I couldn’t get it out of my head what my friends had said to me. They were beating around a bush and I wasn’t sure why.
That night, after a few more drinks, my girlfriends called their parents to tell them they would be sleeping at my place that night. The estate had plenty of space for guests and they came over so often my mom had given each of them a room for when they wanted to sleep over. They made it their own and even kept a few pieces of clothes in the closets and bras and panties in drawers. After a shower and tidying up, we all met up in the lounge in our pajamas. We made it a habit to always wear matching pajamas when they stayed over and tonight was no exception. We wore white cotton t shirts with a broad boat cut, and linen trousers with baby blue pinstripes. It was like our uniform and we wore them proudly.
We were in the process of drinking evening tea to push off the potential hangover that was sure to creep up the next day when my mom came home. We hadn’t even noticed she left the house we were having so much fun. But she must have been out for hours.
“Come out her girls and help me with these bags, I have some things for you”, she called to us.
We looked inquisitively at each other, but I could see Chloe and Becky were holding back grins. In the foyer my mom stood in a flowy pink dress with her hair up in a large ponytail. Her strappy platform heels gave her an imposing posture and I couldn’t help but feel envious of her in that moment. She began handing us matching bags of various sizes, first to Chloe, then to Becky, then to me. But when she got to me, she came in close to my ear and whispered “These are special for you. I hope you enjoy them.” She kissed me on the cheek.
“But mom, we never go shopping. What is all this? It’s a bit much don’t you think?”
“No no honey, we save our money so we can have opportunities like these. Summer is here and it is a beautiful time of your life, you’ll never have another one like it. Just go with it and enjoy.”
She clicked off towards the kitchen to make a martini after a long day of shopping but turned around just as she was about to disappear behind the threshold. “Go upstairs and put these on…Maybe one of you two should help Chrissy slip into hers.” She held a grin as she clicked out of sight.
We were obviously drunk and found the remark amusing. My mom always called me Chrissy since I was young, but never referred to me as “she” before. But she was right, the summer after graduating high school is a unique opportunity. For most people this is the last time they will hang out with their high school friends. It’s the last time we’ll still be young. After this summer, adulthood abruptly approaches and pushes everything else to the side.
We ran upstairs and gathered in my room to go through the bags. We were giddy with excitement to see what awaited us. But what I noticed was all of these bags had come from boutique women’s stores and cosmetic shops, even mine. What were in these bags? A part of me thought the girls knew because they were overly excited and kept looking towards each other with curious grins that didn’t go unnoticed. Something was up, that was for sure.
On the handle of the largest bag hung a note that read, “Open this first. Save the small bags for later. Don’t open the Sephora bags until she’s ready.”
What the fuck did “until she’s ready” mean anyway? Was Chloe or Rebecca the “She”? and why was the order so important?
We dug into our largest bags. Rebecca was the first the reveal the contents. A silk bubblegum pink pajama set. Pants, blouse, hair scrunchy and eye cover. All fine Egyptian silk. We stopped and marveled at the texture of the blouse, it was beautiful. Then Chloe pulled out her contents. The exact same set. And finally it was my turn. I reached into the bag and felt the same silk texture as Chloe and Rebecca’s set. I pulled out the pajamas, and just like theirs mine was bubblegum pink with a scrunchy and all. My heart skipped. Something deep down in my gut fluttered with excitement. But I didn’t act on the arousal.
“What is this? This can’t be for me right?” I asked, but I already knew the answer.
“Of course it is silly! We have to match otherwise it’s no fun”, Chloe said.
“But what would I do with the scrunchy? My hair is kind of long, but not like yours.”
Becky responded, “that’s no problem girl, we’ll show you how to wear it.” They giggled together.
I held a blank expression. This couldn’t be real. My mom went out and bought us matching pajamas for women. I’ve been called “she” and “girl”. This night was shifting into something else it seemed. Then there were the other bags. What could possibly be in those I wondered.
The girls put the pajamas back in the bag and began diving into the medium sized one. Chloe was the first to remove the pink shoe box and opened it wide for us all to see. Inside were beautiful 3″ kitty heel night slippers. The same bubblegum pink as the pajamas with a large bow on top of the foot. She screamed with excitement, then we all dug in and pulled out our boxes. But when I opened mine, my jaw dropped. In my hands were the exact same heels as my girlfriends. Same pink color, same large bow. This was too much now. “I’m not wearing these” I though to myself. But the only thing that came out was, “…What?”
“Chrissy, it’s okay. We have to match and these are so cute, don’t you think?” Becky slurred a bit when she said this.
“She’s right Chris, it may be new to you, but I think you’ll learn to like how they feel when you stand in them.” Chloe had no idea I already knew how heels felt and loved wearing them. But I had pushed that side of me deep down many years ago.
“I don’t know about this”, I said. “I know I’m not very masculine, hell I’m even pretty feminine. But I don’t think this is something I’m okay with.”
They both starred at me, clearly looking for the words to say when Rebecca spoke up.
“Babe…we’ve talked with your mom. We’ve talked with her quite a few times over the past couple months actually.” She hesitated, not sure how to come out with it. “We know you like to dress up in women’s clothes, your mom told us all about it. We know that you think you like girls, but the three of us all agreed, maybe your confusing liking girls with envying them.” She sipped her tea.
“Honey, let us help you understand yourself. You cant keep this down forever. Be free girly, embrace who you are.” Chloe said this with an air of older sister explaining that two plus two must make four.
I was taken aback by this. I had dug that part of me deep down, but I suppose regardless of how deep my femineity was, it was still there all the same. My chest swelled up as I began to feel the burdened emotions that Ive suppressed for so long and a tear came to my eye.
“I just…I don’t know what to say. When did you speak with my mother? Why did you keep these conversations from me all this time?” I began to openly weep into my palms.
Chloe lifted my chin up so I had to look her in the eye. “Chrissy, we love you. You’re mom loves you. And we are your best friends. We’ve always known you were one of us. We just didn’t know what to say or when to say it. And your mom, well she knows you, girl. She wants you to be your best self and as of now this is not it.” She ran her finger up and down my chest. “This summer, let us help you embrace who you are babe. You owe it to yourself to enter University as the girly you want to be.”
I wept harder now, tears streaming from my face. But the burden in my chest had relaxed and I was more at ease. I reached into the pajama bag again and held the silk delicately in my hands as I pondered.
“Okay. We’ll see how it goes… But if it’s too much for me and I don’t want to take it further, please respect that.” I wiped my eyes with a tissue Becky had given me. Unbeknownst to me, not wanting to take it further was never going to be an issue. I was feminine at heart and the closest people in my life knew it. They knew what they were doing, even if I didn’t.
With the burden removed, Chloe began tapping her finger on the smallest box, gesturing for me to open it. She clearly already knew what was in the box. They knew all along.
I opened the small box. It was stripped pink, with gold lettering embossed on the front that read, “Victoria’s secret”. I swallowed as my heart beat heavily in excitement. I opened it to find three sets of panties, a thong, and g string. The panties were pink with white polka dots, but the thong and g string were black.
“We knew you would like the panties, but we weren’t sure if you were a thong girl or a g string girl.” Becky giggled.
“I…I’m not sure. Ive only ever worn a thong from my mom’s closet. I liked it I suppose, I like how my butt cheeks sort of swallow it. You know?”
“Oh, we know girl. Personally I love a nice lacey thong, but Becky here prefers the g strings.”
Becky added, “They basically feel invisible when you put them on. Like nothing is there. It’s amazing!”
I built up the courage to go for it. “I guess we’ll just have to see!” I giggled with them. Chloe put her hand over the box again, indicating something else was in there.
“Keep digging”, She said.
I removed a cardboard insert at the bottom and found a beautiful bralette in the same bubblegum pink as the pajamas and panties. I felt another wave of butterflies overcome me as I held it up to see in the light. I was giddy. My very own set of panties and a bralette. I smiled with satisfaction.
“See girl, that is what I’m talking about. Embrace it honey, you’re one of us from now on.” Chloe said this and pushed my shoulder in a friendly gest. I love the both of them, and my mother too. They understood me.
“Let’s try them on! Come on, what are we waiting for?” Becky exclaimed.
In shear excitement I was about to drop my pants and put on the panties when I realized my two friends were still standing there.
“Aren’t you going to go change in your rooms?” I asked.
“Your kidding me. We’ve been doing this our entire lives. Chloe and I have seen each other naked a thousand times already. You’re our sister babe. Just be cool and put the damn panties on.”
“But I have a penis Becky, I don’t know. Wouldn’t it be weird?” They stared at me perplexed.
“That’s a good joke. You think we haven’t seen a dick before? Come on.” Chloe said
“Yeah, what difference does it make? We’re all girls here, so what if one of them has a bigger clit than us.” Becky laughed and lovingly pinched my cheek.
I was apprehensive, but I obliged them. I felt as though I didn’t really have a choice. If I were to be one of them truly, I shouldn’t have to worry about being naked in front of them. It wasn’t in a sexual way, just girls having fun at a slumber party.
The girls sensed their point had been made and began taking off their pajamas. First the shirt, then the pants. Both of their bodies had developed well and their B cup breasts flopped as they took off their bras. Their breasts were full and their nipples were wide and puffy. They looked at Chrissy as they began lowering their pants.
“Come on girly, just do it”, Chloe said.
I finally got over the butterflies and began striping it all off like them. First my shirt, which revealed a bare flat chest and little nipples which were beginning to harden from the cool air. Not having hair on my body from the eyebrows down made me look like a girl however. Before she went through puberty of course. I felt a little ashamed, caught between two worlds. I was neither a man, nor a woman. I had no sense of who I was. I couldn’t keep living my life as a man, that much was clear. But taking the full step into becoming a woman seemed daunting to me.
My girlfriends had taken off their panties and revealed two beautiful pussies. Becky had shaved a landing strip over hers, but Chloe was completely hairless down there. On her hip was a little heart shaded into her tan. I asked about how she got it, since it didn’t look like a tattoo. She laughed and explained when a woman goes into a tanning bed, they offer stickers to put on so the tan creates an image when removed. jessicamariebennett924@gmail.com 👅🍆🍆🍆🍆
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