Dan + Lindsay 2: Our First DateStory by messyman88Posted 7/30/21 1412 views
Hey everybody, since you all liked the store of how I met my wife so much, I'll continue with the stories of us dating. And obviously, nowhere better to start than the beginning.
Since the night she came over, she was in full on tease mode. She ran every morning and would send me a picture of her sock and shoe choices for it. Lindsay had told me I had to give the first pair of socks that she gave me back to her that Monday but she changed her mind and told me to keep them another week, and by the end of that week they...well, they had seen some heavy use. To class she tended to wear her Birkenstocks more than anything although on warmer days a pair of black rubber flip flops or those Adidas slide sandals that everyone used to wear with socks would come out. I knew it was only a matter of time before it would be too cold for anything that I could see her feet in, so I just enjoyed while I could.
Anyway, about a week after our first encounter and her teasing me non stop, I decided it was time to go on an official first date. Neither of us had been the dating type before college so we were kinda awkward when it came to planning dates. Finally we agreed we would meet Friday night at the campus dining center and eat (romantic, I know...), work out in the rec center, and then hang out in one of our rooms. She was much more athletic than I was, she was a distance runner and I think even did some field events, meanwhile I played t ball when I was little and played basketball when they forced me to in gym class. Needless to say I did not get the athletic gene. But, I did enjoy a good workout, and I enjoyed the thought of seeing Lindsay in her workout gear. And my dreams were fulfilled: as I waited for her outside the rec center, she came up wearing a black school hoodie, the tightest black Nike leggings that hugged her every curve, and these light gray and pink Saucony runners that looked pretty new but nicely used. If she was wearing socks I couldn't see them. Her hair was up in a ponytail that made her look absolutely adorable. She ran up and gave me a quick hug, and a peck on the cheek. "Shall we?" I said and pointed towards the entrance for the dining center, like a total dingus. Luckily she found it cute, and we headed in and stuffed our faces.
After eating, we headed to the rec center. Friday night at the rec center wasn't exactly a crowded time, in the whole place there were maybe 10 people there, including employees. We scanned our IDs at the door with the guy at the front desk who was either very apathetic about being there or high as a kite (or both), and went into our respective locker rooms to put our things in. "So what should we do first?" she said as she came out. I told her I was up for anything, so she suggested we do a light track and field workout and maybe shoot some basketball after. I didn't have a better idea so I let her lead the way. We started with some basic stretching (she's EXTREMELY flexible), did some medicine ball exercises (which SUCK), and some push ups and sit ups. "Hey, I have an idea" she said as I was holding down her feet for sit ups. "You wanna make a messy bet?" I mean, she know good and well I did. She suggested a quick 100 meter sprint race, loser gets a pie in the face. Yes, she was a runner, but she was a DISTANCE runner. Distance runners are not necessarily made for short term speed, so I thought I may actually have a chance. There was absolutely no one else on the track, which was raised above the rest of the workout equipment on a ledge. We lined up on the white lines, and realized we had no way to signal the start without one person having an advantage (if you're the one saying go, you know when you're going to do it so you can get a slight jump). There was a big digital clock on the wall that showed seconds, so I suggested we go when the next minute came so it would just be a matter of reaction time (I watched a lot of drag racing growing up, so I knew all about reaction times). We lined up, her in a 4 point stance like it was a track meet - but those leggings were working overtime holding her backside in, and I was enjoying the view. The seconds part hit 00, and we both took off. I immediately remembered why I don't run much, but I held my own. She edged me by maybe a foot and we both pulled up, breathing heavy. "Not bad!" she said, looking back at me. I told her I was surprised it was that close, but that this wasn't over yet. We made several other smaller bets while working out, and in the end I was getting 3 pies to her 2.
Then came the big bet.
We finished our workout with basketball. Remember I mentioned I played in gym? Well I was actually halfway decent at it, but I wasn't about to let Lindsay know that. I asked if she wanted to make this a really big bet and she nodded, smiling evilly. I suggested we play HORSE. For the first letter, you get a large bottle of chocolate poured over your head. For every letter after that, a piece of clothing gets cut off and another pie smashed in your face. Loser gets another bottle of chocolate and has all their clothes - down to underwear - cut off. "You're on" she said, with an even more evil smile. "Since you're down, you can shoot first." I took the ball, and decided to try to play bad at first. I stood at the free throw line, and intentionally clanged one off the rim. She took the ball and drained a 3 pointer. "Oh wow, I haven't ever been very good at this!" I gave her a mocking smile, and took her place. Off the backboard, off the rim, and out. Thats a bottle of chocolate on my head. She missed her next shot, and I made a free throw. She clanged it off the rim like I did intentionally the first time, and all of a sudden we were tied and both would be getting a bottle of chocolate poured on us. I made a nice 3 pointer, which I knew she wouldn't make, and she didn't. I mockingly told her I couldn't wait to cut her hoodie off her, and she gave me a very clearly fake pouty face. I proceeded to beat her 3 rounds in a row, clinching me the ability to cut off her t shirt, leggings (!!!!!) and socks. I decided to show off a bit, and went for a long 3 point: swish. I pointed out this was her last chance to not have her underwear covered in chocolate, and she took the ball, and....
Miss.
I started pumping my fist and pretending to high five invisible people like I just won something major. She stood there and watched me bask in the glory of victory. After I finished gloating aloud, she walked up and hugged me, giving me a quick kiss. "Good job babe!" she said, while also noting she didn't know I was that good. When she kissed me she pressed her body up against mine a bit more than all the other times we had kissed. I was definitely going to enjoy this.
Her roommate was out of town for the weekend again so we agreed the best place to go would be her apartment. After running to my dorm to let me get a change of clothes (and her socks) we got in her car and headed to a grocery store near her apartment. She had just gotten paid so she agreed to buy everything. We needed 3 big bottles of chocolate, about 10 tubs of cool whip, and some plates to use as makeshift pie tins. My mind was racing knowing what we were about to do. Coming up to the checkout, she actually knew the girl working. "Hey Linds!" she said, her nametag revealing her name to be Brianna. "Bri!" Lindsay (Linds?) squealed in return. "Oh, uh, this is my boyfriend Dan" (We were boyfriend/girlfriend? I'm not complaining at all, I just didn't know we were official) and I waved. "Hey Dan!" she said, way too peppy to be working a grocery store checkout at 10PM on a Friday. Lindsay explained they were both pledging the same sorority (I was going to be dating a sorority girl????). After a 5 minute quick conversation, we said bye and headed to Lindsay's apartment.
Her apartment was really nice, a bit small, but it was only her and her roommate and neither had much so it worked. I did the usual "nice place you got here" routine when we walked in. She smiled and threw the grocery bag on the counter in the bathroom, and locked the front door. "You want to go first?" she asked, standing in the door frame of the bathroom holding a tub of cool whip. I nodded, and gave her a kiss on my way through the door. I sat down in the tub while she answered a text on her phone. I was owed 4 pies and a bottle of chocolate. Lindsay piled 4 plates with cream and took the little plastic thing off the bottle of chocolate. "Which one first?" she asked me. I told her the pies, and she wasted no time picking one up and SPLAT it went in my face, dripping down onto my white t shirt. I barely had any time to recover before the 2nd one came, further covering my shirt and dripping down to my shorts. "Get up!" she told me, and I did, then she motioned for me to turn around and face away from her. Before I could say anything she pulled down my shorts and smacked one pie on my butt and one pie on my front, covering my boxers on both sides. "Hey!" I quipped at her. She smiled. "I know these clothes are all getting cut off me so I wanted to get you good and mad first. Now, don't forget the chocolate!" I actually had. I remained standing as she emptied the bottle over my head. It felt so good running down my shirt, legs, and some was even running down my legs into my shoes and socks. She stopped short of emptying the whole bottle on my head, giving my mostly clean gray and blue Asics shoes some attention with the rest. "They were too clean!" she said, as I closed the glass door and turned on the water to clean myself off. I told her to go get the scissors while I finished. Those clothes were getting ruined.
By the time she came back, I had taken all my clothes off and put them in a laundry bag that could go directly in the washer when we were done. I actually didn't intend for her to see me naked this fast, but...whoops. And she saw EVERYTHING if you know what I mean. She didn't seem to mind. I opened the door and started toweling off, and started reaching for my clothes. She grabbed my wrist. "Why don't you wait on those?" She said, looking at my little soldier standing at attention. I smiled and kissed her while she brushed her hand against it, and I pointed for her to get in the tub. I asked her in which order she wanted to do things, and she shrugged and said it didn't matter. So I picked up a pie, and SPLAT it went in her pretty face, dripping down her hoodie. I took another pie and smacked it on the top of her head like a hat, filling the hood of her hoodie and covering her ponytail. I grabbed the scissors and began cutting the hood off, while she whimpered in an attempt to make me feel bad that wasn't working. After it was detached, I put it on her head while I cut the remainder of the hoodie open, revealing a little white tank top that was about to also get cut off, poorly concealing her black sports bra underneath.
Pie 3 was smacked into her face, and a bottle of chocolate emptied over her head. Her whimpers changed tone a bit, and I thought I caught her hand rubbing between her legs a bit, but I didn't say anything. Her once white but now chocolate soaked tank was cut, first the straps, then the main body, revealing her black Nike sports bra and perfect body. The next pie went directly onto the bra, and she made no attempts to hide she was touching herself anymore. I told her to flip over, which she did. Pie 5 went onto her butt, covering and soaking the doomed Nike leggings. She sat back down and held her legs up to me, and I snipped a slit in the bottom of her leggings and began ripping: they ripped surprisingly easy. I then saw why she was touching herself so readily: no panties. I almost came right there and then.
I told her I had an idea. I took off her Saucony sneakers which had mostly escaped unscathed to this point, and poured half the bottle of chocolate in each. She was wearing socks, a white pair of Adidas no shows. She put the shoes back on, the chocolate pouring through the mesh and out the tops. I handed her one of the 2 remaining pies and told her to do whatever she wanted with it. She smashed it in her crotch, much to my delight. I picked up her leg and foot and began cutting the laces off the sneaker. Then the tongue. Then the sides. I handed her the other pie, she did the same, and she got off as I finished trashing her cute running shoes. Finally, her socks were cut in two and she lay mostly naked except for a sports bra and remnants of her clothes in the tub. I caught her looking at my erection, and asked if she liked it. "Mhmm. I never have before, can I?" I nodded, and she began to stroke it. Her skin was so soft I knew I wouldn't last long, and I didn't, shooting massive ropes all over her sports bra. "Oh wow, that was a lot!" she said, admiring the glaze job I had done on her. "Hand me the scissors." I did, and she proceeded to cut the sports bra off. "There! Now we match." I looked at Lindsay's naked body in awe. I had never wanted anything as bad as I wanted her. "Now, why don't you get dressed and go watch TV while I clean up?" So I headed into the living room and turned on the TV.
She came out wearing a pink bathrobe and likely nothing else, as I didn't see her bring a change of clothes in with her. She sat down next to me and leaned her head against my shoulder, checking her phone. I kept watching the football game I had found, it was some local prep matchup that was supposed to be a big deal but I just had it on for the noise more than anything.
"Hey Dan?"
I looked at her.
"What did you think of Bri?"
I was a bit taken back by this question. It came out of nowhere. As I thought about it, she was alright. Nowhere near as pretty as Lindsay, but good looking. Not as athletic as Lindsay either. The grocery store uniform did her no favors either, although I did like the black and white Nikes she had on.
"Well, I'll be honest with you. Before we met I was very into the idea of experimenting. That's how I met her, through that fetish app. Now I'm very attracted to you, but I just want to try it once. She feels the same way, she's dating too but they aren't serious yet. If it makes you feel better, you can be there too. She's interested in WAM too but has never tried it. I think it could be fun, what do you think? I just don't want to wait until we're more serious and feel bad about doing it, and I don't want to always wonder what it's like."
I asked her when and where, and smiled. She smiled big, and sent a text (presumably to Brianna - Bri? What should I call her?). We started making out, my pants starting to swell again, and Lindsay's phone buzzed. They found a picture of Bri wearing a knee length skirt, very revealing top, and black one inch heels that walked the line of cute and comfortable, and she asked if that would be ok.
Oh yeah, this was going to be fun.
Part 3 to come...