My Date with Lorrie

My first job after college was at a small Greek restaurant called Pirro's on the north end of my old hometown. I would have preferred to have been doing something a little more exciting than waiting tables, obviously, but the economy was tough that year and I hadn't been able to find any jobs after graduation. So I was forced to move home, and for about six months I lived in my parents' basement and worked at the restaurant.

It was kind of an interesting working situation in that I was the only guy who worked as a server. All of the others were women. And while that might sound good in theory – it did to me. I'd been kind of a shy guy and had never had a girlfriend at that point – working with all women is a little different in practice. At least for me it was. The girls used to tease me all the time, and talk about sex and boys right in front of me. They used to love making me blush and laughing at me. After a few weeks I pretty much resigned myself to not having a shot with any of them. Oh well, I thought. What else could I expect?

There was one girl, though, with whom I was convinced I had a chance. Her name was Lorrie, and even though she would tease me just as much as some of the other girls – in fact, she was probably one of the worst at times – she also really seemed to be interested in talking to me. We began to take a lot of our meals together between shifts. I talked a little bit, about school or my family or the jobs I was applying to. But mostly I just listened. I think she liked having a confidante, and I liked hanging around a beautiful young woman. I learned that she was a little older than me at twenty-five, and that she had an associate's degree in communications, but what she really wanted to do was go back to school and study marketing. Her family had split up when she was young and she didn't talk to her dad much anymore. She was dating an auto-mechanic who sounded more and more like a jerk the more I heard about him. She constantly complained about the things he did, like missed dates and unreturned phone calls. Some days she seemed on the verge of tears about him and on the verge of a breakup, but then the next day she'd be talking about how in love they were. It was confusing to me.

It seems a little foolish in retrospect, but the more time we spent together the more I thought Lorrie and I could be together. She had to break up with her boyfriend eventually, right? The guy seemed like a total asshole. And she seemed to like flirting with me, telling me I had pretty hair or nice blue eyes sometimes. Her long legs and platinum blond hair began to haunt my dreams. She surprised me once by hugging me tightly after one of our meals together. I could feel her large breasts pushing into my chest and her bra strap on her back.

"Thank you for being such a good friend," she said, and then actually kissed me on the cheek! I felt lightheaded and aroused for the whole rest of my shift, and completely forgot to put in a dinner order. The manager gave me hell, but I didn't care. Lorrie liked me! She had actually kissed me! It was one of the first times that had ever happened.

Later that same week Lorrie asked me if I would go shopping with her the following morning. She needed some help picking something out. I said yes so fast she looked a little taken aback.

"Wow," she said, "That's great. I mean most guys— Well, I'm glad you're coming. I think it will be good to have a guy's perspective. Can I pick you up at ten?"

"Definitely!" I said.

The other waitresses learned about our shopping excursion somehow and teased me throughout the night. I think they knew what a crush I had on Lorrie. "Ready for your date, Aidan?" they'd ask and giggle. I ignored them. Honestly I was thrilled that they were calling it a date – maybe that meant Lorrie had, too?

I could hardly sleep after work that night I was so excited, and the next morning I was up early to shower and shave and put on one of my nicest outfits. My parents asked what the occasion was and I told them about the "date." My dad said something about it being a little early for that, but they didn't say anything else. I was out on the curb waiting at 9:55. And I waited. And waited. Thirty minutes later I got a text from Lorrie. 'sry. running late. b there in 15.'

I stayed outside in case she showed up sooner. My mom poked her head out the door and asked if everything was all right.

"Yeah, Lorrie's just running a little late," I said.

Mom gave me a funny look and went back inside. Another thirty minutes passed and Lorrie pulled up in her green Corolla. She looked tired and was dressed in sweats and Ugg boots. Her hair was tied back in a ponytail and her eyes were covered with oversized sunglasses. She made no mention of being late but just said, "Man, I am SO hung over right now!" and laughed.

I felt a little disappointed. She didn't seem particularly dressed-up or "date-like," but she still looked good to me and she seemed willing to talk. I held out hope. "You went out last night?" I asked.

"Yeah, just with some of the girls from work. Ashley says hi. You should have come!"

For some reason I was embarrassed to say that I hadn't been invited. "Oh, I was a little tired last night,' I said.

Lorrie shrugged. "And then Travis and I were up late having a big argument... Anyway, we're going to head over the big mall in Preston, is that all right?"

I nodded, secretly thrilled at the first part of what she had said. There must have been a reason she was telling me she had had a big argument with her boyfriend.

"This is going to be so much fun," she said. "Some of the girls and I were talking and we think you'll be great for this."

We made small talk the rest of the way over to the mall. Once we were at the mall I realized that she had never told me what it was we would be shopping for, so I asked her.

"Didn't I tell you?" she said. She started to laugh a little bit. "Sorry, I guess I didn't. I need to buy some new underwear. I thought it would be good to have you there to help me pick them out. Is that Ok? Aidan?"

I hardly heard the last part of what she said. In one car ride she had said she'd had a fight with her boyfriend and that she was taking me lingerie shopping. This had to be my big shot.

"And plus," Lorrie said, continuing with a playful smile, "if you play your cards right, you just might get to see me try some of it on. How does that sound?"

I felt like the floor had tipped sideways. I think my jaw fell down to about my navel. Lorrie laughed.

"I thought you might like that," she said. "But I'm not making any promises...yet. Like I said, you'll have to play your cards right. Think you're up for it?"

As we walked through the mall I began to get really nervous. What if I messed this up? How was a guy supposed to act when he went underwear shopping with a girl? Cool, right? Or excited and into it? I wished I had more experience with girls. I just kept telling myself to stay calm.

Lorrie led me through the crowds and past the big department stores. Lorrie looked great from behind, even in rumpled sweat pants. We walked towards the big pink-lit sign of the Victoria's Secret in the corner of the mall and I froze up a little bit outside the entrance. Inside I could see a crowd of women milling around scantily-clad mannequin and racks and racks of colorful lingerie. None of them seemed to realize what a momentous occasion it was. This was a store I usually hesitated to even walk by, much less enter, and now I would be shopping in it with the most beautiful girl I knew. Lorrie noticed that I had stopped and laughed. "Come on, Silly," she said, and grabbed my hand and pulled me inside.

It was just one step from outside the store to inside the store, but I felt like I had entered another world. My head filled with the smells of perfumes and body lotions. There was so much pink everywhere – pink banners, pinks signs, pink bras and panties. Artistic photos of nearly naked women adorned the walls. I turned and almost collided with an armless mannequin dressed in a see-through babydoll. It was hard to focus and follow Lorrie amidst all that sexy stimulii, but she held on to my hand and led me like a little child all the way to the back of the store. I was in a complete daze the whole way. There she met a pretty dark-haired salesgirl that she knew.

"Sarah!' Lorrie said, and hugged her. They spent a few moments greeting each other while I hovered a few steps behind. I've never really been sure what to do in those kinds of awkward social situations. Eventually Sarah looked up an noticed me.

"Is that--?" she asked, looking at Lorrie.

"Oh, no," Lorrie said, looking briefly back at me. "That's Aidan, from work. I've told you about him, remember?"

Sarah seemed to smirk. "Ha-ha, Aidan. That's right. Nice to finally meet you. I'm Sarah, Lorrie's roommate. I've heard all about you."

I wasn't sure what to make of that exchange. So Lorrie had been talking about me with her friends. That had to be a good thing, right?. But why had Sarah made that strange face?

"So what can we do for you today, miss? The usual?" Sarah asked in a sarcastically professional voice.

Lorrie laughed. "Something like that. I need something really awesome for tonight."

"What's the occasion?"

Lorrie looked back at me again before answering Sarah. "I told you before, remember? Let's just say I want to go all out."

Sarah smiled again, mischeivously. I started to feel like they were putting on show for me for some reason. "Hmmm, I think we can probably find something that will work. Come on, let's take a look."

The girls began to make their way around the store, stopping to talk at just about every large display. Apparently, different set-ups featured different "lines" of lingerie with their own names and selling points, but I couldn't really tell the difference, other than the fact that the underwear kept getting lacier and skimpier, and that I kept getting more excited. Lorrie made me carry her purse to free her hands up as she walked and picked things up, as well as a large mesh bag that Victoria's Secret gives to its customers to hold lingerie in while they shop. As we walked around, the bag began to fill up quickly. I felt a little silly carrying a purse and a bag of underwear, but I was also glad to be carrying something that I could hold in front of me for, well, the obvious reasons.

Lorrie and Sarah seemed to be having a lot of fun shopping together. They laughed and giggled in their high-pitched, feminine voices and the sound was like candy to my ears. As time passed they loosened up even more, and at each display they would hold up bras and panties to themselves and each other to see "how they looked." They'd grab each other's arms and touch each other, flirtily playing around. At one point Sarah smacked Lorrie's behind, and even from a few yards back I could see it jiggle with her sweatpants. It was making for a great show, and once again I couldn't help but think that they were putting some of it on for me.

After that, the two of them stopped at a table covered in brightly-colored bras and began to whisper to each other, giggling. After a moment, Lorrie lifted her head and called me over. I assumed she wanted to put something else in the bag as she'd been doing all morning, but instead she held a lacy bra right up to my chest. "Doesn't look too bad," she said. She and Sarah giggled.

Sarah picked up a pair of panties and held them against my butt. "These could work, too. Or should we get the matching pair?"

"Cut it out," I said meekly, embarrassed that they were doing this in front of everyone in store. A few curious glances had come our way, and the girls were making a lot of noise.

"Shhh," Sarah said, and smacked my butt. "You're making a scene." I started to blush.

"I bet you'd look pretty good in lingerie," Lorrie said.

Sarah sized me up and down. "You know, Lorrie," she said, "I think he might me about your size."

"You think so? No way." Lorrie asked, laughing.

"Yeah, actually. Here, let's measure him."

Sarah grabbed my arm and began to pull me towards the back of the store while she pulled a tape measure out of her pocket. It wasn't too difficult for her to drag me. She was noticeable taller than me in the high heels she was wearing, and I was pretty slender back then. I suddenly felt a little panicked.

"Come on, guys," I said. "Stop."

"Don't be such a spoilsport," Sarah said, still laughing. She had a firm grip on my arm.

"I really don't want to," I said, disappointed at how whiny my voice sounded. More customers were looking at us, as well as some of the other salesgirls. It was all very embarrassing. But Lorrie rubbed my shoulder and my already feeble resistance melted away.

"Please, Aidan. It'll be so funny. You just have to do it."

I was helpless. I nodded. Sarah cheered and lifted my arms up and measured around my chest.

"Thirty-four," she said. "Skinny boy. Same size as you, Lorrie. Not quite as much up here, though." She squeezed my chest.

"Hey!" I said.

"Sorry," she said, and pinched my nipple hard. It hurt.

I was worried about what else they were going to do to me in their plauful mood, but fortunately the girls seemed to have had their fun – for the moment. They left me alone for a moment as they went through the bag of lingerie. They talked and took things out as Lorrie seemed to narrow her choices down. Eventually she said, "Well, I've got it down to three different sets. Can I try these on here, Sarah?"

"The bras, yes. The rest of it, no. Sorry, but it's store policy."

"Well, damn," Lorrie said with a big theatrical sigh. "Now what?"

They both seemed to think for a moment. Again, for whatever reason, I got the strange feeling I was watching a kind of performance.

"The store does have a very generous return policy, though. You could take things home and try them on there, then I could return them for you next time I have to work."

Lorrie decided that that was a great idea. There was one snag, however. The three sets of lingerie she'd picked out were very expensive – the total cost was almost $400!

"I just don't have that much cash on me," Lorrie said. She paused to think. "Aidan, do you think you could put it on your credit card for me? I promise I'll pay you back after I return the stuff I don't want."

"I don't know," I said. "That's a lot of money." I wasn't exactly rich in those days.

"Please, Aidan. And remember what I told you earlier?" She put her hand lightly on my chest when she asked. That was it. I was done.. The possibility of seeing Lorrie in that skimpy lingerie would have been enough to make any man spend that kind of money.

"Promise to pay me back?" I asked.

"Oh, Aidan!" she said and hugged me. "Thank you."

The hug almost made up for the pang I felt as the cashier, another pretty salesgirl, slid my credit card through the machine. I just hoped my parents wouldn't get a chance to see that credit card statement.

After I paid and the salesgirls bagged everything up, we waited a little bit for Sarah to get off work. I was disappointed that it wouldn't be just me and Lorrie going to her house, as I thought it made it less likely I would get any. But the disappointment was relative. I was still very excited to be going to Lorrie's house at all, and I thought that if I got the chance I would tell Lorrie how I felt about her.

Once Sarah was finished we all piled into Lorrie's car, the two girls in the front and me in the back with the pink Victoria's Secret bag on my lap. You can imagine how excited I was during the ride to Lorrie and Sarah's house. Dreams of what might happen were playing on constant loop in my head. Never in a million years, though, could I have imagined what actually ended up happening.

Once we got to the house we all walked into Lorrie's bedroom and Lorrie asked me to put the shopping bag on the bed. I was so excited that it slipped off the edge and onto the floor. Lorrie and Sarah laughed. They took the lingerie out of the bag and arranged the it all across the bedspread. Three lacy, frilly, sequined bra and panty sets; one in turquoise, one in hot pink, and one in dark black. Each set also include a matching garter belt and pair of sheer stockings. Just seeing the lingerie laid out on the bed like that was enough to make my heart rate rise.

"It's so hard to decide!" Lorrie said, surveying her (my) recent purchases. "We're just going to have to try all three sets on. Sarah, which one you want to start with?"

Oh my God, I thought. Not only would I see Lorrie in lingerie, I'd see her friend, too. I could not believe my luck.

"Hmmm, I'm liking the turquoise."

"I thought you might," Lorrie said. "I think I'll go black for starters. Very sexy. Which means Aidan here gets to try on the pink!"

At first, I wasn't sure I'd heard her right. "What?" I said, dumbly.

"Sarah's going to the wear the turquoise set. I'm wearing the black. Which means you get to try on the pink one. That way I can see what all three look like at once. It will make my decision easier."

"Don't look so surprised," Sarah said. "Three sets of lingerie and three of us. How else would we do it?"

What I had been expecting was to see one or two beautiful girls wearing skimpy lingerie. I did not expect to be wearing it myself! I didn't say that though. Instead I said, "Yeah, but it's girl stuff, and I'm—"

"What? A man?!" Sarah said with a shriek of laughter that really hurt my feelings. I suddenly felt ready to cry or leave or both. This was not what I had hoped for. This was humiliating.

Lorrie was gentler. "Aidan, it really wouldn't be fair for just us to put on little tiny bras and panties while you stayed in your regular clothes, would it?"

I had to shake my head. "No, but—"

"Come on, Aidan," Lorrie continued. "It won't be so bad. It's just us. You know we won't tell anyone else.. And you'll get to see two very sexy girls wearing nothing but lingerie. Don't you want to see that?"

I was being persuaded. And at the back of my mind there was a faint hope. Maybe this was all just a strange way for her to seduce me. It might be worth it.

"And all you have to do is put on some silly little underwear. It's not such a big deal, really, is it? It will be fun. For all of us. I promise."

I nodded, slowly. What choice did I have? This was the girl of my dreams we're talking about. She probably could have convinced me to do anything.

"Great," she said. "Sarah and I are going to get changed in the bathroom. You can get dressed out here. But if you can't figure out how to put something on, Sarah and I will be out in just a little bit to help you."

The two of them picked up the lingerie and marched into the bathroom. Sarah looked to be on the verge of laughter again and Lorrie was smiling triumphantly. They shut the door behind them and I could hear them moving around and talking in there.

I sat down on the bed next to the remaining lingerie. It looked very small and very girly. I felt lightheaded again. What had I gotten myself into? I picked up the bra. It was surprisingly light. The front was detailed with pink sequins, and the back felt soft and spongy. The panties were tiny enough to fit in the palm of my hand. I realized I had no idea how to put any of it on, but I wanted to at least try before Lorrie got out. I didn't want to disappoint her.

I got undressed and folded my clothes up neatly on a chair. I felt ridiculous and exposed standing there naked. I jumped when I heard a loud laugh in the bathroom and running water. I sat down on the bed and marveled at how different the silk bedspread felt against my bare skin. I decided to start with the panties as they seemed the most straightforward. I looked at them and wondered how they would ever even cover me. The tag said size small.