Dating Lindsey Ch 01

I've never been great with women. In High School, I never had a date to the prom, I've never had a girlfriend, and it seemed like no matter what I did, I could never find a girl interested in me. It always seemed like the cute girls went for the jerks, and the nice guys always get left behind. I guess you could say I got friendzoned early and never got out of it.

In college, I was hoping things would be different. It was my freshman year when I figured I'd have a blank slate. I was 18, and no one knew who I was, and better yet, there were plenty of other 18yr old girls breaking it off with their high school boyfriends.

Things weren't so simple. It had been a few months and it seemed like I had found myself right back with being "just friends" with every girl I met. Even Tina, the kind of girl that bounced around in a low-cut top and sat in the front row so professors could get a view, didn't want anything to do with me. She and I became good friends, because, as she has said, she feels like she can trust me and I'm not just hanging out with her for her looks. Though honestly, I'm not even sure I would know what to do with her if I had the chance.

"Listen, I'm sorry Jenny gave you cold shoulder last night," she said to me one day, sitting next to me in the cafeteria on Sunday morning.

"It's fine," I said. For once she was in a modest pair of sweatpants and sweatshirt, though I had seen her last night. She had her regular Saturday clothes on. Lots of cleavage up top, and a crazy short skirt over her legs. "Just one more rejection, right? I don't get it. I'm really nice, I'm not bad looking. I just keep striking out."

She gave me a look like she wanted to say something she shouldn't, but held it back. She thought for a second while she chewed on her low-grade college food. "Sorry, I'm so hung over. Ended up blowing these two guys after doing those everclear shots. Remind me never to do that again," she said, rolling her eyes. I gulped, imagining the situation. She looked at me defensively "don't worry, I didn't swallow," she said with a sigh.

I exhaled, only getting frustrated with hearing her Saturday night hijinks. "Well, that's a relief," I said, sarcastically.

"Ok, ok. You know what? I met this really cute girl at the party and she will be great for you!" she said excitedly.

"You're just telling me now?"

"I had a lot to drink last night. What was her name? Oh right, Lindsey. She was saying all night how she hates going out with those annoying jocks. I think you guys will be perfect."

I was just desperate enough that some girl Tina met at the party drunkenly was starting to sound like a great idea. Plus, that little bit about her wanting the nice guy instead of the jock-type was music to my ears. "Well...hook us up," I said, pressing it.

"Ok, you know, I think I will," Tina said with a smile. "Friend her on Facebook. Lindsey. She's really cute. Brunette. Big boobs. D cup I'm guessing. I know how you like big boobs," Tina said with a wink, eliciting a red face from me. "And I'll put in a good word, ok?"

I nodded, thinking, staring down at my plate. "That's great Tina. Thanks, I mean...really thanks."

Tina smiled. "Oh hang on, it's that guy I slept with last night. Don't let him see me" she said, hiding her face.

I friended Lindsey just as she advised, and she was indeed very cute. Tall, thin, brown hair. I was paging through a few of her photos after she accepted my request, and she was definitely hiding a nice rack under her shirt. Fortunately, she didn't seem to be the flashy type. Talking to Tina more, Lindsey wasn't as "engaged" as Tina was with most of the guys at the party. I surmised that she had been dragged along by her friend, much as I had been to these obnoxious frat parties.

One day she messaged me back. I had asked her out on a date, and to my surprise she gave an enthusiastic yes. We were set for Saturday night.

I went wide-eyed when Tina stopped by my room Saturday afternoon, about an hour before I had to leave for my date with Lindsey. "That's not what you're wearing, is it?" she asked, hands on her hips in my doorway.

"That's not what you're wearing is it?" I said back to her, looking her up and down. She had a v-neck sweater on, and her boobs pushed together in between it. Long black boots and a tight micro-skirt. The look made me salivate, even though by this time you'd think I'd have gotten used to it. I just knew she was in for trouble tonight.

"Ok, ok, comeon. Clothes off. Let's get you into something decent," she said, coming over, undoing my shirt.

"I can do it. You're not my mom. Just give me some privacy. Turn around."

"Grow up. It's college. And trust me I've seen it all before," she said, helping me slip my shirt off. She looked my chest over and made a face. "You've got to start working out. No offense...anyway let's get these pants off," she added, reaching down to start undoing my belt.

"Hey! Let go," I said, startled.

"Hush, you cannot wear pleated khakis on a first date. What is this, your first recital?"

I was about to interject when I thought to myself that these pants might have indeed been worn to a recital or two. But I was interrupted by her tugging my pants down quickly. "Hey!" I said again, suddenly just in my boxers in front of her.

"Now lets' see," she said, looking through my clothes, clearly displeased with the selection. Finally, she found a button-down plaid shirt she liked and a pair of jeans. I wasn't in any position to disagree with the choice.

"Wait...why aren't you wearing these?" Tina asked, finding a pair of boxer-briefs I had.

"Oh I just wear those for working out," I explained.

"And you thought a pair of gray boxers were better?" she said, almost scolding me.

"Well...I don't know. Plus what does it matter?"

She gave me a look. "I can't believe this is what I have to work with. Get those off! Trust me, she's going to want to see your package squeezed into these."

"I thought you said she wasn't one of those girls," I said.

"Well, no but, you never know when you're going to get lucky. You don't want her stopping at these," she said.

I blushed and even got a little aroused at her attitude, talking about and looking down at my crotch. I looked down and looked back up to her. She got a mischievous look on her face and went over to pull my boxers down.

"Shit...hey!" I said, covering myself a little late.

Tina giggled. "Wow...not too bad. Where were you last week? You would have put those guys to shame."

"Stoppit," I said, embarrassed, obviously showing on my face.

"Chill out. Now comeon, get these one, I won't look...too much," she said with mirth, covering up her eyes half-way cartoonishly. I gave in and put my boxers on quickly, covering myself up. She handed me my jeans and shirt, and finally I was dressed.

"There we go. Much, much better. Now you're meeting her in her dorm right? Wow, at least take her to dinner first."

"I am," I said sternly, trying to regain back some dignity. "It's dinner and then she said we could watch a movie."

"Yeah a movie and what else?" she asked, pantomiming a handjob in the air.

"It's just a first date..." I repeated with some hesitancy, swallow hard watching her hand. I was excited at the idea that maybe her joke would come to life.

"Well, don't get too many ideas. She's a nice girl from a nice family. Real conservative. I was over there and her mom was on the phone with her like bitching her out. Anyway, I need to get going. Good luck tonight," she said smiling and waving.

"Yeah you too," I said back to her, trying to find my cologne.

"Looking for this?" she asked, holding up a bottle of Axe. "Yeah right. I'm doing you a favor," she said, tossing it out in the garbage on her way out.

I was beyond nervous walking up to her door. To make matters worse, I was the only guy in an all-girls dorm, passing by women giving me looks. I suppose they all had an idea of why I was there.

I found her room and knocked after a deep breath. Though I expected Lindsey, I instead found an older woman, dark hair, opening the door. "Are you Jake?" she asked, sounding pushy.

I swallowed hard. If I wasn't so surprised by her forwardness I might have noticed that she was pretty attractive, for someone my mom's age. "Uh, yeah," I said, swallowing hard.

She looked me over, making a face. "I'm Lindsey's mother. You can call me Mrs. Oran," she said, extending her hand. I shook it awkwardly and she let me inside. "Lindsey's in the shower, which is good because I wanted to have some one on one time with you. You're dating my daughter, is that correct?"

I tried to put on my best face. Totally taken back by this discussion, I nodded. "Yeah. We're uh, going to dinner." Part of me wanted to run right then and there. I had no idea what was going on.

She smiled, and I got a better look at her now that my mind had been cleared a little from the initial shock. She wore a business outfit, or at least something formal. It was a black skirt down to her knees and a black jacket over a white blouse. I could see the family resemblance, especially in the chest region. "Now listen" she said to me, engaging my eyes. "Lindsey is a nice girl and I want only the best for her."

"Yes...yes ma'am," I said nodding. She reached over and touched my arm, squeezing it. "I take it you don't play football," she said condescendingly. "You at least better be getting good grades. I won't have a party-boy dating my daughter!" she insisted.

"No...no of course not," I responded.

"Let's see what we have to work with down here," she said reaching down and undoing my pants.

"Hey! Hey...what are you doing!" I demanded. Jeez eighteen years of getting nothing and two women were getting my pants off.

"Get your hands away from there," she said sharply, slapping my wrists away. "Boxer briefs, good choice," she said with an approving look before she tugged the elastic. I let out a yelp as she let the elastic snap against my balls, and she tucked it underneath them. I swallowed hard, and got that feeling that you get when you dream you forgot your clothes in the middle of class.

"Hmmm, not too bad at all," she said approvingly, hands wrapped around my cock, running her fingers over it, grazing over my balls. "Not the best, but it will do. It's a lot better than her last boyfriend that's for sure," she said, snickering. I could only force a smile.

"Oh my...I see. You really aren't a party boy are you." She said giving me a knowing look as her hands now grasped a hard cock. "Stiff already. And when was the last time?"

"Last time...what?"

"You know," she said, jerking my cock up and down.

"Ohhh...ohh..." I said first in surprise then in pleasure. "Oh uh...I dunno."

"Comeon, don't be shy. We've gotten to know each other well. When was the last time you gave yourself release?"

"Um...two nights ago."

She smiled. "Good. I won't have my girl going out with a chronic masturbator as well. In fact, I'm actually a little worried about this right now," she said, squeezing my erection. I was completely hard, despite my nervousness. She cupped my balls and let her other fingers tickle my cock a little. "We can't have this happening all night can we?"

"Um...no," I conceded. "Sorry..."

"Now now, that's ok. I remember being your age. And the guys were even worse. Trust me, the 70s was not a good time to be a woman."

"Oh..."

"Anyway, I have just the thing for this guy," she said tapping my cock. She reached back into her purse, and fished around, pulling out an odd looking contraption.

My face went a little blank as I looked at her hold it.

"This will take care of your little...issue" she said, and reached down, cupping my balls. "Now just relax," she said soothingly as I felt her fingers grip my balls and squeeze.

"Oh...oh ouch" I said, squirming as I felt her hand compress my balls. I was too shy to do anything and I sat there feeling her squeeze me until I went soft.

"That's it. Perfect" she said, happy with herself as she took the contraption and put it around my cock, slipping me down inside of it, and tucking my balls behind. "That's it...don't worry."

"What...what is this thing?"

She waited until I looked up at her and said slowly, seriously. "This is just a device to make sure you don't get any of those pesky...erections during your date with my Lindsey." I heard a snap, but was locked with her eyes. "There we go." She rubbed my balls in her hands. "Feel that? Getting a little snug huh? Don't worry, this will curb your young hormones a little," she informed, and indeed I could feel my cock expanding but pushing against the sides of what felt like a plastic tube. I looked down and indeed my cock was trapped inside, a ring around my balls. On top was a lock, which gave me a nervous feeling in my stomach. I saw Lindsey's mom slide a key around a necklace across her neck, clasping it behind her. I could put two and two together.

She smiled. "Don't be nervous. You just be well behaved tonight and you won't have anything to worry about."

I gulped hard and my natural shyness kept me from saying much. She helped me zip my pants back up and I sat there afraid as she turned the tv on, acting as if nothing strange had happened.

Finally, Lindsey came out of the bathroom with a towel around herself, her breasts pushing out the top. "Oh! Jake you're here...sorry," she said, embarrassed. "Mom, I'm in my towel, jeez, could have warned me." she said. I averted my eyes and I heard her sneaking back into her bathroom to get her clothes on.

"Nice huh?" Her mother asked, looking at me for a response. "I was like that at her age."

"Oh yeah...I guess."

"Well don't get any ideas. Remember," she said, dangling the key around her neck. "If you ever want to masturbate again, you'll treat her with respect."

"Yes ma'am," I said assuredly and Lindsey came out wearing a cute shirt with a cardigan over it, and jeans. I could see that Tina was right and she definitely hid a nice pair of breasts underneath. Plus, she was fit, like every 18 year old college girl was. I could already feel myself tight in the tube again.

I stood up and faced her. She smiled. "Thanks for coming over. I hope my mom wasn't too annoying," she said, looking over and giving her mom a look. She stood close to me and I felt butterflies in my stomach.

"I normally don't do this, but Tina said such nice things about you. It's nice to meet a guy that's like, not drunk at a party" she said with an appreciative smile.

"Yeah, you too," I said sincerely.

"Ok, mom, I think we can take it from here," she said, giving her a look. "Wait...mom what are you wearing around your neck!"

"Oh, dear, don't take that tone with me. You know I care about you."

"Mom!!!" she whined. "You can't just lock up my boyfriends."

"Darling. You know how men are. It's for their own good. Now you can look forward to a well-behaved gentleman on your date," she said with a confident smile, not compromising at all in her tone.

She looked down and put a hand at my crotch, squeezing, feeling me in my tube. "Oh my gosh...you are wearing one! Mom this is so stupid. I'm eighteen and in college. I'm an adult, you can't cage my boyfriends anymore."

"Lindsey. Now don't you take that tone with me or else you are not going on this date. I've been in college before and I know men. Your father was like this too. Getting...erect...all of the sudden. Now it's nothing to be ashamed of. It's just for your first date. I don't want anything inappropriate happening."

Lindsey sighed and I could see her bend under her mother's will. "Ok, mom, just...can you leave us alone?"

"Yes, dear, it'll be like I'm not even here. You two just carry on and you will have a nice evening. I'll stay completely out of it."

I bit my lip. She was going to dinner with us? Lindsey didn't seem surprised. "Oh...well, I guess that's not that bad." Her mother came up and patted her arm. "See? You're right. You are an adult Lindsey. Now why don't we get going? Jake don't sweat it, remember, it's like I'm not even here!"

We ended up heading to a local place, Finnigan's, while Lindsey and I sat in the back seat together awkwardly. I would say that it reminded me of High School, or that it had been one of the most awkward dates in my life. In reality, this was really one of the only dates I had been on barring a few get-togethers with girls. Yet, I don't think anyone would call my evening normal, though at the time I was a little too wrapped up in my date with Lindsey to really grasp the situation that I was locked up in my date's mother's cage.

Dinner was fairly uneventful. I gave the usual talk about my school plans, and struggled to keep up the small talk with Lindsey. It was challenging trying to act like her mom wasn't there, who chimed into the conversation every now and then. The most embarrassing part was fortunately the time Lindsey had gone to the bathroom. I was stuck there with her mom while she teased me about being locked up and her holding the key. She was two wine glasses in by that point and dangled the key around her neck. She asked me if it was getting snug, and I said yes. She smiled and said "You've certainly been well-behaved this evening, but I guess that's because I've got you by the balls, huh?" she said, laughing, touching the key around her neck. I could only bashfully look down at myself after that.

I hadn't really considered the gravity of the situation until the end of the meal, when it was clear Lindsey's mom wanted me to take care of the check. I had my credit card, but I knew the bill would be near sixty dollars, and I wasn't expecting to have to cover everyone's meal.

I blushed when Lindsey's mom just gave me a look and put a few fingers on the key and slid the check over to me. I looked over to Lindsey and she just smiled, clearly accustomed to this. I just put my credit card on top of the bill and tried not to notice Mrs. Oran's arrogant look over me. I guess she really did have me by the balls.

We finally got back to Lindsey's room and I was surprised at how comfortable the device on me was getting. Even though the implications of the lock made my stomach churn, I was getting regrettably used to the idea.

Lindsey and I sat on her futon, while her mom found a chair off to the side. Then, Lindsey put in a movie, and smiled at me while she moved closer, urging me to put my arm around her. At that point, all the worries of the night went away a little as I felt her body under my arm, holding her. It felt good to be at that point. Lindsey was certainly cute, and for the first time I had been close to a girl without just being friends.

It was probably the best half hour of the evening, holding Lindsey and watching the movie, but I heard her mom, about halfway through the movie say "Well aren't you going to kiss her?"

"Mom, stoppit. You said you wouldn't say anything."

"I'm just saying, you guys are holding hands and his arm is around you. You might as well move in for a kiss, dear," she said to me. I looked to Lindsey and it was clear she agreed. Under pressure, I moved in for a kiss on her cheek, and a cute smile from Lindsey as she turned her body to mine and moved in to kiss me more, this time on the lips.

We made out, my hands rubbing her arms and legs, her hands over my chest. It was easy to forget her mom was sitting there watching as I felt her soft lips on mine and the electrifying feel of her hands running over my chest. I hoped I wasn't too awkward, and also I hoped I was doing everything right. However, the incredibly enjoyable experience of making out with this cute girl was having its effect on me, and I could feel myself hardening inside the device. I shifted uncomfortably, as I felt Lindsey's hands roam over my thighs, and the passion increasing.