The 39 Year Old Virgin

Author's Note: I'm thinking of doing more single stories like this one. Every time I post a story I am flooded with comments and emails to continue, but I've noticed that the additional chapters get less and less reads. For example Trophy Wife has 44k, but Trophy Wife 5 only has 8k. I'm thinking people enjoy the solo stories more, so I'm gonna try to do more of those. Anyway, I'm rambling, so please enjoy:

THE 39 YEAR OLD VIRGIN

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!

ONE MONTH EARLIER

I am sitting on my friend's couch watching TV. It's Friday night and I've been coming over every Friday since she got divorced. We would typically order takeout and pop a bottle of wine after her 3 year old son Mikey went to sleep. We have been friends since high school, but never more than that.

"Big day coming up in a month," she said, referencing my 40th birthday.

"Yeah, whatever," I said, not wanting to think about being that old.

"Oh come on, I was a good sport when we celebrated my 40th last month," she said.

"That's true," I said.

"Anything special you want to do?" She asked.

"Not really," I said.

"Why don't I set something up? You can invite the guys and I'll invite some hot girls!" She said.

"Nah, I'm good," I said.

She put her hand on my shoulder and shoved me slightly, "What's the matter with you? Why don't you want to go out and have fun?" She asked.

"Oh, I don't know, I...I'm always tired from work, My...my back always seems to hurt, and I..." I stuttered.

"Excuses, Excuses! All of your friends are either married or out chasing broads. Even my ex was doing that while I was pregnant. You sit here every Friday night with a 40 year old divorced mom of a 3 year old!" She said.

"Gee, if you don't want me here I'll go," I said, pretending to be insulted.

She hit my arm again, "You know what I mean," she said.

"Then why don't we get married," I said, only half kidding.

She laughed a little too loudly and said, "Yeah, right. I'm never getting married again after that last scumbag! You wouldn't want me anyway."

She was wrong, I would marry her in a heartbeat, but she clearly wasn't interested. Being friends was fine by me.

"But in all seriousness, why aren't you out there looking for a girl to settle down with? Or at least have some fun with?" She asked.

I shrugged.

She paused for a second and said, "Wait, are you gay?"

"What!" I screamed. "No way!"

"It's ok if you are, you know my brother is gay. You two would make a cute couple," she said, winking.

Of course I knew her brother Paul was gay. In fact he used to hit on me all the time. He would touch me ever so slightly, but enough for me to know he was doing it. I was always too embarrassed to say anything or tell him to stop. There were times where he wouldn't be as subtle and make comments like: 'You know it's common for a brother to hook up with his sister's friends.'

"Fuck off!" I said, a little upset.

This time she rubbed my shoulder and said, "I'm just messing with you, but there's gotta be a reason you're not out there trying to find a woman."

"I don't know. I get nervous. I mean I've never..." I cut myself off before I revealed my secret. Unfortunately it was too late.

"You've never what?" She asked. "Holy shit are you a virgin?"

"No!" I shouted unconvincingly.

"No freaking way! How does that happen?" She said loudly.

She pushed my arm again in shock, but this time I was holding my wine glass. Red wine spilled all over my shirt. I stood up quickly.

"Tara, what the hell!" I said.

"Don't get any wine on my couch," she said.

"Your couch? My shirt is ruined!" I said.

"Relax, I'll get you a new one, Max left some clothes behind when I kicked him out," she said.

Max was her ex-husband. Towards the tale end of her pregnancy he started to lose interest in her. It got even worse after she gave birth and he ended up sleeping with women all over town. I always thought he was a douchebag and she was too good for him.

She came back with a t-shirt and handed it to me. I took it and started walking towards the bathroom.

"Where are you going?" She asked. "You can change here."

"Um, I was going to go in the bathroom," I said.

"Why?" She asked.

"It's just..." I stammered.

She gave me a funny look and said, "What are you hiding from me?"

I didn't answer and she reached for my wine soaked shirt, grabbing a hold of it.

"Come on, change your shirt," she said.

She had a strong grip on the fabric and the momentum of me trying to get away caused my shirt to rip open, exposing my second secret of the night. My huge man boobs were exposed and Tara was staring right at them.

"Whoa Nick, you have tits!" She screamed.

I tried to cover them up, but it was no use.

"Wow, I thought I knew you. That's two secrets I've learned about you tonight!" She said.

I reached for the clean t-shirt and asked, "Can I please have the new shirt now?"

"Not until you tell me the story of those spectacular breasts. What are they, a C-cup like mine?" She said giggling

"I don't know. I've never measured. Whatever, can we sit down? I'll tell you whatever you want. Just let me have that shirt," I pleaded.

She threw the shirt across the room and took my hand.

"First you tell me everything, then you can have a shirt. I want to check you out first!" She said.

"Fine," I said.

I sat back down on the couch, shirtless. Tara's eyes went right to my chest and she was staring. This is the first time any woman had seen me without my shirt on. In fact the only person who has ever seen me with my shirt off was my doctor.

"So how did you end up with boobs? She asked.

"It started when I was a teenager. I went for a physical and the doctor said I had something called gynecomastia. They were small looking breasts and they just seemed to grow as I got older," I said.

"So that's why you always wore a shirt in the pool?" She asked.

"Yep," I said.

"And that's why you're not trying to pick up women?" She asked.

"Uh huh. I'm scared about what the girl would think when I took my shirt off. What happens if she laughed? If she tells other people? What if mine are bigger than hers?" I said.

"Oh sweetie, I'm sorry. Why didn't you just have them removed?" She asked.

"I looked into it, insurance wouldn't cover it and it's expensive to pay out of pocket," I said.

"It would be a shame to lose them, though, they are a beautiful set of breasts!" She said.

"But I'm a guy, I'm not supposed to have beautiful breasts!" I said.

"How do they feel?" She asked.

"I don't know," I said.

"How can you not know? Don't you wash them in the shower?" She asked.

"Well yeah. I guess it feels kinda nice when I touch my nipples," I said, revealing too much.

"Like this?" She asked.

She reached over and started to rub my right nipple. It hardened instantly and I moaned.

"I think somebody likes this!" she said.

I didn't respond. She scooted closer and grabbed my left nipple. She was rubbing both of my breasts and nipples and it felt amazing. I threw my head back and closed my eyes. My dick sprung into an erection in my pants. She looked down and saw it.

"Now, I know you love this! She said.

She stopped massaging me and sat back. I whimpered in disappointment.

"Hey, I wonder if these are why you're back hurts. Girls with boobs like us need support," she said.

I wondered if she was right, and didn't even notice the fact that she referred to me as a girl. She stood up and I reached for her like I wanted her to stay and play with me some more.

"Hold on, I'll be right back," she said.

She came back with one of her bras, a black lacy one. I had a surprised look on my face.

"And what do you plan on doing with that?" I asked, nervously.

"I just want to see something. Stand up," she said.

"You don't think you're gonna..." I said.

"Let's test my theory. Turn around," she said.

"Fine, but just for a second and this stays between us," I said.

She put her hand to her head like she was about to salute and said, "Scout's honor!"

She put my arms through the loops and the straps over my shoulders. She clasped it in the back and spun me around. Then she adjusted my breasts in the cups and took a step back.

"How's that?" She asked.

"Feels weird, but kinda nice," I said.

"And your back?" She asked.

"It's like a weight has been lifted off me," I said.

"Aha, see, all this time you just needed a bra!" She said.

"Very funny," I said, reaching behind me to take it off.

"What are you doing?" She asked.

"You had your fun, now I'm taking it off," I said.

"Come on, you admitted that it makes you feel better. It's just you and me, wear it for the rest of the night," she said.

"Seriously?" I asked.

She pulled her shirt over her head, exposing a similar black bra. Her tits were amazing. Sure I had seen them in a bikini, but this was the first time I had seen her in her underwear.

"Here, now we're even!" She said. "Sit down and I'll get us some more wine."

I was tired of arguing so I sat down on the couch. She joined me with the bottle of wine and we sat there, me in my bra and her in hers.

"My bra really looks great on you," she said. "You should think about wearing one all the time."

"Yeah right, that would really help my social life," I said, sarcastically.

"It doesn't have to be a sexy one like you have on now. You could wear a sports bra under your shirts. No one would know and it would relieve so much pressure on your back," she said.

"I don't know about that." I said.

"I'm just trying to help. You can wear the sexy ones all the time if you want," she said, winking.

"You know what I meant!" I said.

"Ok, let's make a deal. I'll go out and buy you some bras. When you come over next Friday we can have a fashion show and you can decide what you like. If you don't like them, I'll return them and we can forget about it," she said.

"And what do I get out of this deal?" I asked.

"Besides comfort for your back?" She asked.

"Yes," I said.

"Ok, let's make it a birthday present. If you agree to let me play dress up with you, I guarantee you'll lose your virginity the night of your 40th birthday.

"And I can decide on this next Friday night?" I asked.

"Yes, take a week to think about it," she said.

"Ok, but don't get your hopes up," I said.

"One more thing, I want you to wear your bra home tonight," she said.

I noticed she referred to it as 'My Bra' and said "Come on!"

"What's the big deal? You've had it on for an hour already and I bet you don't even notice it anymore," she said.

"Well, yeah," I said.

"So, then wear it home and keep it for the week. Maybe you'll enjoy it wearing it at home," she said winking.

"Fine, but again, don't get your hopes up. Can I at least have that t-shirt now?" I asked.

"Ok, you'll be wearing something of mine and something of my ex's. That's kinda hot!" She said.

"Yeah, whatever," I said, putting the shirt on.

I kissed her goodbye and drove home. I'm embarrassed to say that the second I got home I stripped down to just the bra and jerked off while looking in the bathroom mirror, staring at my lace covered breasts.

I got through the weekend and Monday without thinking about the bra I had put in one of my drawers. It was Tuesday when I caved. My back was killing me and I needed some relief. I stripped down to my boxers and put on the bra. I made dinner and sat on the couch to watch TV. I barely noticed it was on and my back felt so much better.

On Wednesday I raced home from work to put my bra on. I was too scared to wear it to work. It was such a pleasure to have it on again. The same thing happened on Thursday. I was sitting on my couch in my black lace bra and boxers again when Tara texted.

"Hey Sweetie, just making sure you're coming over tomorrow night," she asked.

"I'll be there as usual. Should I bring pizza?" I asked.

"Sure. Mikey is staying at my Mom's so we have the house to ourselves," she texted.

That was an interesting way to put it. The next text was a picture. It was a rainbow of colors of sports bras and bras similar to the one I was wearing.

"Just giving you a preview," she said. "I'm so excited. Now don't lie, how many times have you worn your bra this week?"

I was already thinking of it as 'My Bra' and now she used the words 'Your Bra'. I was starting to think this was getting a little exciting, but then I got shy about it.

I started to type 'I'm wearing it right now', but then I reconsidered. I erased the text and lied.

"None. I hope you saved the receipt for that stuff," I wrote.

"I'm not worried. After our fashion show tomorrow night, you'll be putty in my hands!" She texted.

"We'll see about that! See you tomorrow night!" I replied.

I put down my phone, because I had something more pressing to take care of. Actually it was my dick that was pressing. It was rock hard against the waistband of my boxers. I quickly pulled them off and walked into the bathroom. I jerked off again while looking at myself in the mirror. This time I rubbed my one breast through my bra with my free hand. I lasted less than a minute and blew a huge load into the sink. I guess wearing bras was exciting. I didn't know what was going to happen tomorrow night, but it was certainly going to be interesting.

My workday on Friday seemed to take forever. I kept looking at my watch and time was just crawling. Finally when the day was over I sped home and changed into some casual clothes. I ordered the pizza and picked it up on the way.

Tara surprised me by answering the door in her robe. She had a pink lacy object in her hand which I noticed as she kissed me hello on the cheek. I put the pizza down in the kitchen and she handed me a pink bra.

"Here, put this on and we'll have dinner," she said.

The fabric of the bra felt nice. It was similar to the one that I had been wearing all week, but it seemed a little thicker.

"I thought we were going to talk first over dinner," I said.

Tara dropped her bathrobe and she was wearing a pink bra and thong. Her boobs looked tremendous.

"Come on, don't you want to be twins?!" She said as she batted her eyelids.

"Whoa," I said.

"Just put it on, it will be fun!" She said.

My dick was stiffening in my pants and I couldn't say no to her. She had an amazing body. She had worked hard to lose the pregnancy weight, and she looked gorgeous. I ripped off my shirt and put the bra on. I adjusted my man boobs in the cups and they seemed bigger than usual.

"You liar!" She said. "You put that bra on like a pro! You said you didn't wear the black one all week. There's no way you're that good at putting one on without practice!"

Damn, I was caught. I didn't confirm or deny anything though and asked, "Is this bra different? It seems to be making my breasts bigger."

"Enjoying your first push up bra, huh," she asked, giggling.

"I thought this was supposed to be a comfort thing," I said.

"Yeah, I got you some things for comfort, but I decided that when we are alone together that we would dress sexy. I can go change if you want me to." She said.

I did not want her to change. I was enjoying the view and if I had to wear a push up bra to keep looking, so be it. We sat down and ate our pizza.

"Explain to me again what our deal is?" I asked.

"Simple. I bought you some sports bras in black, white, and grey for you to wear all the time, and then a nice selection of colors in sexy ones for us to enjoy together," she said.

"So I would have to wear the sports bras to work?" I asked.

"Well yeah, isn't the point to ease your back pain? Your back must hurt at work too, right?" She asked. "That's why I bought basic colors. I wouldn't expect you to wear red or pink at work.

"And the 'sexy' ones?" I asked, using air quotes.

"They're for all other times. Like when we're together or when you're alone at home. Are you ready to admit you enjoyed your black bra yet?" She asked.

"Ok, yeah, it was nice," I answered modestly.

"How many times did you put it on?" She asked.

"Three," I said, still shyly.

"Anything else you want to come clean about?" She asked.

"Last night I masturbated while wearing the bra and rubbing my nipple," I said, embarrassed.

"Holy crap! That's hot! I knew you'd be into this!" She said.

"I haven't said yes, yet," I said.

"Are you kidding, your body is answering for you. I can see the impression of your hardon in your pants and while we were talking your left nipple slipped out of your bra and that's hard too!" She said.

My face turned bright red.

"Tell me what I get again?" I asked.

"On the night of your birthday I promise you will lose your virginity," she said.

That promise made it all worth it. Don't get me wrong, the bra did feel nice and it helped with my back pain. It also made me kinda horny, but in the end I was doing this so I could finally lose my virginity to Tara. I was secretly hoping that finally sleeping with a woman would give me the confidence to go out and find a woman for myself.

"So I play this game with you and on the night of my birthday I get to have sex? You're not gonna back out, right?" I asked.

"I swear. You keep playing dress-up with me and I guarantee you will finally lose your virginity," she said.

"Ok, deal," I said.

She led me into her bedroom and the fashion show began. We started with the sports bras, which were boring compared to what I had been wearing. They were perfect for work though. They seemed easy to cover up and most importantly they helped keep my breasts hidden. The support was great too.

The sexy bras were next and those were my favorite. It was weird thinking that I had a favorite type of bra, but it was fun trying on all different styles and colors. The best part was Tara bought two of everything. Every time I changed, she changed. I finally got a peek of her naked boobs each time we put on a new bra. She commented: 'Don't worry, girls change in front of each other all the time.' Again I disregarded her referring to me as a girl.

I wore a black sports bra home and to bed. I spent all weekend in various sexy bras to try to figure out what style I liked best. Of course it was the push up bra was my favorite. On Sunday afternoon, Tara texted to ask if I was wearing one of my bras. This time I didn't lie and sent her a picture of my bra encased boobs. She replied with a heart emoji and a fire emoji.

I wore the sports bras to work all week and nobody noticed. The second I got home each day I changed into one of the sexy ones. I started sleeping in them too. Tara continued to ask for pictures and I was always happy to send them back. This would all be worth it when my birthday came in two weeks.

Friday night came and I picked up Chinese to bring over. Mikey was at his grandparents again, so Tara could give me her undivided attention. This time she gave me a peck on the lips when I walked in. She was wearing a t-shirt and jeans this time. We sat down to eat, fully clothed this time, which was a little disappointing. When we finished eating she finally asked to see my sports bra. I quickly took my shirt off to show her.

"You look great!" She said.

"Aren't you a little overdressed?" I asked, prodding her.

"Oh, does Nicky want to see my titties again?" She teased me.