My buddies and I, Brian Miller, turned eighteen this year and we chose to go across the bridge to celebrate New Year’s Eve where we could drink. The drinking age in our state was 21, over in Staten Island it was 18. I went over to James’s house. James would drive, but when he went out to start his car he called back in, “Why is your Dad in the car across the street?”

“There’s no good reason unless he’s suspecting I planned to go out drinking. You’re probably going to need to go without me,” I told him.

James said, “I will around drive to the block behind us; go out back and cut through the Edward’s yard behind us and I’ll pick you up there.” He drove around the block, but my Father soon followed him. James called back and said he was sorry, but he and Randy weren’t waiting.

I returned from Edward’s home and asked his sister, Vivian, “Could you give me a ride home? I knew she was soon to be going out with a group of friends. Vivian laughed, “Follow me upstairs so we can quickly get you changed. We’re taking you to NYC with us; you might not be drinking much but we’re going to Times Square.” She continues, “First call Derek to thank him so he can take his father’s car and hat back home.”

“Shush about upstairs,” I said, “or your Mom will know why you’re taking me upstairs.”

Vivian had a mischievous smile, “To be dressed as a girl is what I’d say. Don’t worry she already knows. It wouldn’t work to keep it a secret from her.”

I said, “What did you do that for? What did she say when you told her?”

She said, “If it wasn’t me it hopefully would have been someone else who was helpful.” Vivian said, “My Mom hopes it either gets it out of your system or gives you a realistic idea about being a girl.”

Vivian said, “If you are not game to try it say so now, or let me take you upstairs and help the changeover. But we need to make it quick; Eydie, Sandy, and I want to leave in forty to sixty minutes.”

“But will your parents say if I’m dressed as a girl to leaving the house?”

“My Mom, that you are a girly boy planning to go with us. If you don’t think you make a believable girl, you can stay behind, change, and start walking home. I’m sure your dad will give you a ride home if you call him.”

I walked upstairs with Vivian and went into her bedroom. She gave me a pair of panties, a bra, and a pair of pink tights. “The pink tights are because you probably didn’t shave your legs.”

I went into the walk-in closet to change; it was almost as big as my bedroom. I kicked my pile of clothes to a corner and pulled up the panty, enjoying the feel of it, shimmed up the pantyhose after I rolled up the legs. Again the sensation made me feel wonderful, and finally, I put on a satin and lace bra. I was proud that I was able to reach back and hook it behind me.

“I’m coming out.”

She said, “You’re lucky not to have hair on your chest or arms.” She shaved under my arms, put some padding in the bra cups, and gave me a marine blue, medium-weight sweater. They handed me an off-red skirt that went just over my knees. Vivian said, “I’d like to see you do your makeup; because it's crunch time, I’ll do it and your hair. She used a concealer, foundation, and then with my eyes. She put on an eyeliner extended longer at the corner than I would. I commented, but she said, “You’re supposed to be a college student, not a teenager. The eyeshadow was a close match to my sweater in color with silver over it. Then she did my eyelashes, then my eyebrows, having trimmed to style them. “We can modify them before you go home.” She brushed and combed out my hair; I thought I heard her cut someplace; she said, “You won’t notice it.”

Vivian was being nice to me, but I don’t think she knew how much this meant to me, no matter about my thanks or compliments.

She acts to pierce my ears. “We agreed not…” The first poke was made and a loop was put in.” I looked at the loop as I felt the next poke and earring. “You’ll need to move the loop and dab it with a cotton ball of alcohol.”

“They’re pretty, but we agreed no earrings.”

“I told you they were needed! And you now agree they’re good.” Vivian said, “Use the toilet; while I finish getting ready.”

Once done, Vivian went quickly down the stairs and to the car, while I was slower and more cautious. June Bisset asked me to look up and smile; she took my picture. “You make a very attractive young woman. Smile, be confident, and enjoy your evening. “Vivian said your name is Brie or Brianna. If you need someone to speak for you call my number and address me as Mom.”

Viv beeps her horn, and I’m out the door. Viv drove to Eydie’s; Sandy was already there. Sandy and Eydie tease me. Sandy, “I think Tom will be happy to see her.”

I said, “There was no talk of guys.”

Eydie reiterates, “Sorry but guys will keep us warm, our costs down, and they secured where were to be. In the front of the place on Times Square and we’ll have drinks while we wait for midnight, and the luxury of a women’s room nearby.”

We go through the tunnel from Jersey to NYC; it's slow but moving. We were told of parking near Hell’s Kitchen where the guys located us. They take us down and to the back door of where we are going. Once inside I was introduced to the guys; Will Warren was the one I was matched with. He knew of our school but goes to Fordham University with Matt who is part of our group. Trey and Gil round out the group

Will talks, “Hey, Brie is it, relax. I’m taking a double major in business administration and environmental science.”

Vivian interrupted, “He has good hands from playing basketball; watch them.”

“Brie, I know about you; I hope you can take a good poke,” he said.

“I can give and take a good poke.” I turn to Eydie and ask, “I thought it was Tom I was meeting?”

Will spoke, “That was my name in high school. Away from my Dad, I go by Will. And regarding the ‘poke’, you’re the girl. We go out to the front of the place and are caught up in the noise of the crowd. Will’s behind me with his hands on my waist we cuddle. He nibbled on my ear and kissed my neck. He sniffs at my perfume and whispers sweet things. Soon I feel his body pressing against my butt. It's a turn-on. A guy thinks I’m cute enough as a girl he’s turned on.

It's 11:00 and we’re getting cold. Vivian turns to her guy and smiles as he presses against her; they kiss and snuggle, maybe more. Eydie and Sandy are enjoying their guys.

Will said, “If you’re game I can help warm us up. It just takes a little poke.” He was already joking with me, so I’m not sure what ‘the poke’ is. He then pulls down my panty and puts a gel on my butt; when I finally understand,

“Are you okay?” Embarrassed I was so naïve, I’m speechless. It dawns on me, that he’s Tom Warren.

“Tom, I didn’t know.” His rod is pressing against me; he poked me hard enough that it hurt; now he pressed his way into me. “Woe!’ He’s big and it stretched me. I’m relieved as he starts to pull out, but stops and pushes back in. There’s a rhythm with feelings welling up inside.

I didn’t mean to moan, but it felt wonderful and it was building. Tom’s sucking my neck. “Don’t leave a mark!” I heard a laugh. My own body is turned on and I like others am overwhelmed with feelings. I feel his cream inside of me, as my body shakes. He pulls out, turns me around and he forcefully kisses and I’m hugging and kissing him. He wipes me; my butt oozed a bit. I pull my stretched panties back up.

“Is everyone warm?” Sandy asks. “Was that you, Brie?” The other two affirm hearing me.

There’s a countdown of 9, 8, 7, and “Happy New Year.” Will says. I knew he was surprised I didn’t say anything.

“I was ready to stop; I didn’t expect you to want me.”

We talked; I explained I was speechless, but didn’t want to be a little kid. That I feel like a girl.

He said, “I hear you’re very smart, but haven’t applied for college.” A gleam eventually returns to Will’s eyes. We talk more until he is moaning.

I ask, “You’re wanting in again. I guess in for a penny, in for a pound. I’m in a corner, cut off from view, he pushed my panty aside and presses. Enough gel he slips in.

More relaxed, I enjoy everything more, the mounting joy gives way to an orgasm that Will did not let up on. I swooned as he stepped away. Vivian helps me up, “I hope I didn’t force this upon you?”

I asked, “Do you think your Mom will know?”

Will said, “I’m sorry but my sister Joann knew that I was seeing you tonight,”

We stopped at an all-night restaurant close to home. I put on new panties and, like the others, refreshed my makeup. Others, seeing Viv, Eydie, and Sandy, wondered who I was. They finally accepted that I was Brie.

Once we get back to the Bissets, I see my Mom. She hugs me and whispers, “I see you did it. I have mixed feelings, but June said, ‘Your time came.’ We’ll talk later. I knew you had feelings; I just thought they’d pass in time.”