The 39 Year Old Virgin

I hated when she called me Nicky. She rarely even used my name, it was always, Sweetie or Buddy.

"Well yeah, I thought we wore sexy bras around each other," I said.

"Which one did you bring?" She asked.

"I didn't think to bring one," I said.

"Good thing your buddy is always prepared. Why don't you clear the table and I'll go get ready. Meet me in the bedroom when you're done," she said.

I scraped the plates and put the dishes in the dishwasher. I walked back to her bedroom and she was wearing yellow lingerie, a cute bra and a thong. On the bed was more yellow lace, which I assumed was a bra for me. I looked her up and down.

"Are you just gonna stare or are you gonna get dressed?" she asked.

I reached for the lingerie and realized it was a matching bra and thong.

"Um, you bought me panties too?" I asked, confused.

"Yeah, a bra and boxers doesn't really go," she said.

"But the deal was for me to wear a bra, not panties," I said.

"How about I sweeten the pot," she said as she flipped her hair.

"Okay?" I questioned.

"You complete the set, wear the panties that match your pretty bra, and not only will you lose your virginity on your birthday...I'll pay for your breast reduction," she said.

"What? Really? I'd feel bad taking your money," I said.

"Don't worry, it's not my money, it's called alimony and it's glorious," she said, laughing, "I'd love to use that asshole's money to help my buddy."

"And what if I don't want the surgery?" I asked.

"Aww, is my Nicky starting to enjoy her boobies?" She said with a smile.

There's that nickname again. "No, it's...just..." I didn't know what to say.

"Ok, here's my final offer. You wear your bra and panties for me all the time, with the exception of work, up until your birthday. In exchange, you'll get to lose your virginity on the night of your birthday and I'll give you the money equal to the cost of the breast reduction surgery. You can use it however you want," she said.

"Are you sure?" I asked.

This deal was getting better by the minute. So what if I had to wear panties for a week. I was going to finally get to have sex and if I wanted to I could get rid of my boobs. On the other hand I could keep my boobs and buy myself something I need with the money.

"Final offer," she said.

"Deal!" I said, as I reached for the panties.

We spent the rest of the night like we usually did, talking and watching TV. The only difference was we were sitting on the couch wearing bras and panties. That night I wore the yellow lingerie home under my clothes and slept in them. Tara had bought panties to match my bras and sent them home with me.

I spent the entire weekend in bras and panties. Multiple times a day Tara texted me for pictures of my lingerie and asked me to change and send a new picture. I gladly complied and was looking forward to my 40th birthday coming up on Friday.

Surprisingly my week flew. I continued to wear the sports bras to work and changed into my bra and panties when I got home. Each night I sent Tara a picture before she even asked.

On Thursday night she texted me that I should try to get there early on Friday for my birthday surprise. She was going to cook me dinner and then my assumption was she would make good on her promise. I was finally going to get to have sex and I couldn't be more excited.

My workday ended up being great. They had a cake for me at lunch and when my boss asked me about my plans, he volunteered to let me leave early. I didn't even have to ask. I rushed to Tara's house and she opened the door in a bathrobe again. She gave me a big kiss on the mouth.

"Happy Birthday!" She said loudly.

She let me inside and the house smelled wonderful. She didn't cook often, but when she did it was always great.

"Are you ready for your big night?" She said.

"I can't wait!" I said.

"Wonderful, I'm gonna make sure you have the time of your life," she said. "Do you trust me?"

"With my life," I said.

"Wonderful!" She said, "I thought we should have a little more fun before the main event."

"You're the boss," I said.

I would just about agree to anything right now. I was so close to having sex for the first time in my life.

She took my hand and led me to her bedroom and into the bathroom. She turned on the water in the shower.

"Strip," she said.

I quickly disrobed and stood naked in front of her. She had seen me in bra and panties and would be seeing me naked later anyway, so I wasn't embarrassed. She handed me a bottle.

"Lather up with this lotion and don't rinse off until I say so," she said.

I didn't have to read the bottle to know what it was. If she wanted me hairless, that was fine with me. If she wanted me to shave my head, I would've done it.

I covered my body and waited for what seemed like forever. When I got the ok, I rinsed off and watched all the hair beneath my eyebrows go down the drain. I finished my shower and got out to dry off. All my clothes were gone and I knew something was up.

I walked into the bedroom in my towel and Tara was wearing a short black cocktail dress. It was strapless and showed a ton on cleavage. It ended just above her knee and her legs were clad in black nylon stockings. She was wearing 5" heels and for the moment towered above me.

All I could say was, "Damn!"

"You like?" She said, in a cute voice.

"Yeah, but I thought we were staying in," I said.

"We are. I thought it would be fun to dress up," she said.

"But I didn't bring any fancy clothes," I said.

She pointed to the bed. There was a bra, thong, garter belt, stockings, black dress, and a blonde wig.

"We're gonna be twins for your birthday! Except I figured you would want to be a blonde," she said.

I hesitated and then agreed. After all we've been through the last few weeks, if this is what would get me to the promised land, I wasn't going to argue.

"Um, ok," I said, reluctantly.

"Nicky you're gonna make such a hot girl!" She said.

This time that nickname didn't bother me.

"Start with the bra and garter first. You'll want to put your panties on last so you can take them off easier," she said.

My dick throbbed at the notion that I would be taking my panties off for her later.

I picked up the bra and found it to be strapless. I had never worn a strapless bra before, but it was pretty easy to put on. It pushed my breasts together and gave me tons of cleavage like Tara had. I fidgeted with the garter belt and hooked it around my waist. As I pulled the stockings up my legs I got goosebumps up and down my body. The feeling of nylon going up my newly hairless leg was amazing. I gasped.

"Doing ok there Sweetie?" She asked, noticing my delight.

"I can't believe how good these feel! Why wouldn't girls want to wear stockings all the time?" I asked.

"Maybe we need to add them to your wardrobe," she said.

It didn't dawn on me that tonight was supposed to be my last night dressing up and I softly whispered, "Definitely!"

I put on the other stocking and Tara helped me attach the tabs. I slid my thong up my legs and tried to tuck my dick as best I could. She had me check myself in the mirror, and from the neck down I looked hot!

She handed me my wig and said, "Makeup time!"

"Makeup? Really?" I asked.

"You just looked at yourself in the mirror, and your face doesn't match your body. You have to look complete for your big night, don't you?" She asked.

"I guess so," I said.

I put my blonde wig on and sat at her makeup table. I had no idea what she was using on me, but 5 minutes later I had long false eyelashes, black eyelids, light rosy cheeks, and pink lipstick. She also put on false fingernails that were already painted to match my lips. Other than the dick twitching in my panties, you would never know I was not a girl.

Last was my dress. It had a zipper in the back and she told me to step into it. She zipped me up and I was wearing a dress for the first time. It was tight and I liked the way it felt snug against my body. My breasts looked beautiful sticking out of the top of the strapless gown. Tara gave me my heels that matched hers and we were the same height again. She had me do a couple laps around the room to get used to them. She stood next to me as we looked in the full length mirror. We looked like two hot babes, one blonde, one brunette.

"You look amazing Sweetie! I can't believe we're both 40. We could totally pass for 29!" She said.

"Thanks. These last few weeks have been fun doing this with you," I said.

She kissed me lightly on the lips and said, "Ok, let's go eat and then you can have your present!"

Finally! I thought to myself. Losing my virginity wearing a dress and lingerie wasn't exactly how I dreamed this would happen, but losing it to a girl like Tara is the dream!

I walked slowly behind her, still not completely used to my heels. She went into the kitchen to get the food and told me to sit down at the dining room table. I sat down slowly in my tight dress. I looked at the table and noticed there were three place settings.

"Hey Tara, are we expecting someone else?" I asked, nervously.

Just then the doorbell rang. "Surprise!" She said.

What the hell was going on? This was supposed to be our night. My birthday dinner and then my birthday present. Who did she invite? This is crazy!

I stared at the door as she opened it. In walked her brother, Paul. He was wearing a collared shirt and slacks. He kissed her hello on the cheek and she led him to the table.

"Paul, this is my friend Nicky. I believe you two have met, just under different circumstances," she said with a big grin on her face.

Paul took my hand and kissed it, "Nice to see you again, Nicky. Happy Birthday!"

"Thanks," I replied softly.

He sat down and I gave Tara a look like I was mad at her.

"Let me help you in the kitchen," I said to her.

I stood up slowly, but as I did so, my dress rode up and exposed the tops of my stockings and garter clips.

Paul saw and said, "Nice!"

I walked into the kitchen and grabbed Tara's arm.

"What the fuck?!" I said loud enough for her to hear, but not Paul.

"After all the fun you had dressing up, I wanted to test my theory," she said.

"Tonight was supposed to be about me and you for my 40th birthday," I said.

"Technically I didn't say that. All I said was that I promised you would lose your virginity," she said.

"Yeah, to you! Not your brother!" I said, knowing what she was hinting at.

"Maybe there was some intentional misleading on my part, but I just had to know," she said.

"Know what?" I asked.

"The real reason you aren't trying to hook up with girls. The real reason you're now a 40 year old virgin," she said.

"And what do you think that reason is?" I asked, already knowing the answer.

"With the way you took to the bras, then the panties, and now the dress and full makeup, I was thinking that you don't want to be 'WITH' girls, because you want to 'BE' a girl," she said, stressing those two words.

"You're crazy," I said, "I was prepared to fuck you tonight."

"You say that, but would you really have gone through with it? Did you really think I got you all dolled up so you could hook up with me?" She asked.

"I don't know what I thought," I said.

"Here's an addendum to the deal. Play along with me tonight, do your best to act like a girl for Paul and see what happens," she said.

"But he's gay," I said, "Why would he want a girl?"

"He knows who you are and you know he's always had a crush on you. When I sent him the pictures you've been sending me all week, he said he just had to meet you. He said a guy with tits is the best of both worlds," she said.

"Wait, you sent him my pictures?" I said.

"Yeah, sorry I did that, but he thought they were really hot!" She said.

"Really? He thought I was hot?" I asked.

"See you're getting into it already," she said, "Now just play the game one last time. One way or another you'll lose your virginity tonight, plus I'm still gonna give you that money I promised. Let's see what happens, I'm dying to know if I'm right."

"Just so I'm clear, you want me to act like a girl for your gay brother, flirt with him, etcetera, and if I decide I'm not into it, you'll sleep with me, right?" I asked.

"If I'm wrong and you're not into him, then yes, I'll fuck your brains out!" She said. "And cut you a check. I know you need the money."

"Fine. Deal!" I said, knowing I would be fucking her later and going home with some desperately needed cash.

There was no way I would be into Paul. I didn't like guys. I wanted to be with Tara, not her brother. I put on this dress and sexy lingerie to seduce her, not him. I decided I would play along a bit, make it convincing, and then blow him off so I could be with Tara.

She told me to sit down at the table and she would bring the food, because she didn't trust me carrying dishes in my heels. I sat down at the table next to Paul. He had already poured the wine and tilted his glass towards mine.

"Cheers! Happy Birthday!" He said.

I clinked his glass and said, "Cheers! Thanks!"

"Everything ok in there?" He asked. "You two were in there a while."

"Just girl talk," I said, getting into character.

Tara served the food and sat down. The three of us started to eat.

"Who knew my sister had such a beautiful friend," he said, "You know it's common for a brother to date his sister's friends."

I can't believe he used the same line from years ago. He was really going for it. He must've assumed I remembered. It was actually kinda cute.

"Yeah, I don't know why it took me so long to introduce you to Nicky. I think it's because she just found herself," Tara said.

"Well, I'm just happy to be here on her birthday. You look great to sis, but I've gotta say Nicky is gorgeous!"

I blushed and said, "Gee thanks."

We continued to eat and Paul kept making comments about my looks. Tara was piling on too and I was really enjoying my birthday dinner. About halfway through the meal Paul slipped off his shoe and started rubbing my foot with his. The feel of his cotton sock on my nylons gave me the same goosebumps I had earlier. My brain wanted me to tell him to stop, but my dick told me otherwise. I could feel it start to tremble and I was really enjoying the attention.

We had finished our meal and Tara was clearing the dishes. That's when Paul's hand touched my thigh. When we were younger he would always try to rub my leg or lightly slap my ass. That always made me uncomfortable. This was different now, I was completely comfortable, which terrified me.

"Having a good time?" He asked me.

"I'm having a great time! Thanks for making my birthday special," I said, not knowing where those words were coming from.

"It doesn't have to end yet," he said.

"Oh really," I said, totally on autopilot now.

What the hell was I doing? Did I actually want this? Did I want to hook up with Paul? Did I want to be a girl instead of be with a girl like Tara though? Was she right? The whole time he had his hand on my leg and I hadn't stopped him. Maybe that was my brain giving me the hint.

My concentration was broken when the lights went out. Tara came in with a cake with a big '40' candle on it and started singing. Paul joined her in a chorus of 'Happy Birthday'. As they were singing his hand kept creeping up my leg. He reached under my skirt and as they hit the 'To You', he brushed up against my crotch.

My dick had become untucked and a drop of precum had made my panties wet. He must have noticed and rubbed his finger, squishing the liquid around. He gave me a suggestive look and I nodded. I wasn't sure what I had agreed to though. Tara served the cake.

"Hey Sis, were you still planning on meeting those friends later? Because it's fine, Nicky and I can just stay here and continue the celebration," he said.

Apparently that's what I agreed to. Tara had plans to go out and leave me with her gay brother all dolled up. Was this really about to happen? Is this what I wanted, to lose my virginity to Paul? The guy who had been crushing on me for years?

Tara being a good friend wanted to make sure she wasn't forcing me into something I didn't want to do.

"Is that ok with you Nicky? I'll leave you two alone for a bit while I meet up with some friends?" She asked me.

I hesitated for a minute, still not completely sure and said, "Sure, go have fun. We'll be fine."

I had no idea what was going to happen next, but I sure was curious. I had never even thought about what sex with a guy entailed. In the back of my mind I still knew I could back out if I wanted to.

We ate our cake and Tara got a text that her friend was outside. She kissed Paul goodbye and asked me to walk her to the door.

"Nervous?" She asked.

"Totally," I said.

"Don't be. You know deep down my brother is a really nice guy. You saw the way he was treating you all night. Just relax and enjoy your first time," she said.

"I'll try," I said, "I still don't know if I can go through with this."

"Trust me, getting fucked feels amazing. And I'll tell you what, whether you let him fuck you or not, I'll still let you fuck me tonight," she said.

"Let me deal with one sibling at a time," I said.

"That's my girl!" Have the best time!" She said.

I walked back towards the dining room and Paul was already sitting on the living room sofa with the TV on. I grabbed our half full wine glasses and brought them with me. I sat down next to him and smiled. We started to watch TV together and my mind started to go a mile a minute. Am I going to go through with this or am I reconsidering?

My brain began to recap the events that led me to this point. Here I am sitting on my friend's couch on my 40th birthday. She had promised me I would lose my virginity as my present. As I'm thinking, my thigh is being rubbed gently and I have chills going up and down my spine. I feel my dick throb and I'm really nervous. Am I ready to finally have sex? What if I'm no good at it? I'm running out of time as the hand is working its way closer to my crotch. Screw it, I have to know what it feels like, I'm ready!

"Is everything ok, Baby?" Paul asked.

I disregarded his use of a pet name and said, "I'm just a little nervous, I've never done this before."

"Don't worry about. Tara told me everything. Just relax and I'll make it pleasurable for both of us," he said.

I was wondering what he meant when he said she told him everything, but my concentration was broken when he kissed me. Holy crap! My first real kiss and it's with a guy! I felt his tongue touch my lips and I knew enough to open my mouth. His tongue slipped inside and touched mine. Clearly I have no experience French Kissing, so I just relaxed and let him do his thing.

He broke the kiss and asked, "Was that ok?"

"Yeah, it was nice," I said, not wanting to let on it was my first kiss.

"Would you like to do it some more?" He asked.

"Sure," I said.

He put his hand on my chin and pulled me into another kiss. As we kissed his hands got busy. They went right to my breasts and he pulled down the top of my dress. My boobs were quickly hanging out of my bra. He started to rub my nipples as I swallowed his tongue. For a supposed gay guy, he certainly knew how to work a pair of tits. My nipples were hard and my dick got so hard that it popped out of my panties. I couldn't look down just now, but I'm sure it was tenting my dress.

Paul broke the kiss and asked, "Feeling good?"

"Definitely," I said.

"I'd like to go down on you now, if that's ok?" He asked.

He wanted to go down on me? No one had ever sucked my dick before. I had to make sure I knew what he was offering.

"Oh, ok, I thought you would want..." I said nervously.

"You thought that since you're the girl that you would be the one going down on me?" He asked.