Being Jennys Summer Boyfriend

Disclaimer: This story features cuckolding and humiliation. All characters in this story are above the age of 18.

*****

I had pined for Jenny Davis since I first laid eyes on her. All through high school, even just a smile or a glance in my direction would make me flush and sweat. She was so beautiful, with long blonde hair and an hour-glass figure.

She didn't pay a ton of attention to me. I mean, it made a sense, a girl like her had her pick of any guy in the school. She spent a lot of time with the jocks on the football team. But she did sometimes flirt with me in class. She would lean over my desk so that I could see down her shirt, flash me her amazingly cute smile, and ask if she could copy off my homework. I would always give it to her. She and her hot girlfriends and the jocks would pass my homework around for them to copy. Sure, she was using me, but I figured if I showed her that I was smart and nice, she would start to really like me.

Sure enough, on the last day of our senior year, she walked up to me as I was emptying out my locker. "Hey, Lucas," she said, smiling.

"Oh, hey, Jenny," I said.

"So, my parents are out of town this weekend and I'm gonna throw a big graduation party," she said. "You wanna come?"

I was stunned. She'd never asked to socialize with me outside of school before. "Um, yeah, I'd love to!" I said eagerly.

"Great!" she said.

As she handed me an invitation, one of her jock friends, Steve, walked up to her and slid his arm around her waist, resting his hand on her butt. "Oh, hey, Lucas, you coming to Jenny's party?" he said casually.

"Uh, yeah, wouldn't miss it," I said, kind of shyly.

"Cool, see you there," he said, not really paying attention - he was too busy trying to get a look down Jenny's shirt. She giggled and leaned into him. I saw his hand slide down to give Jenny's butt a tight squeeze. "Let's go, babe," he said.

They turned to walk away. I stared after them, then she briefly turned her head and caught me. I blushed, but she just winked at me and smiled. I smiled back and waved.

***

The day of the party rolled around. I put on my favorite button-up shirt and pair of jeans and headed over to Jenny's place. When I got there, cars were parked all along the street and I could hear the music blaring. I approached her door and knocked. Nobody heard me, so I just opened the door. Nearly everybody from school was there, holding red solo cups which, based on the smell, were not just full of soda.

I walked inside. Across the living room, Jenny was standing with her usual circle of friends. She spotted me as I entered, smiled, and walked over to me. "Hey, Lucas! Thanks for coming!" she said, giving me a big hug.

I couldn't believe what she was wearing - just a yellow bikini top and a pair of cut-off denim shorts. I got a thrill as I wrapped my arms around her mostly bare, tight body. "Hi, Jenny, uh, thanks for inviting me," I said nervously, feeling myself start to sweat.

"Help yourself to a drink in the kitchen and then make yourself at home, okay?" she said.

"Okay, will do," I said. I walked into the kitchen. There were bottles of liquor and mixers all over the counter. I opened the fridge, which was almost entirely full of beer. I had never drunk alcoholic beverages before, but I didn't want to look like a loser in front of Jenny, so I pulled a can of beer from the fridge and poured it into a red solo cup. Tasting it, I winced and almost had to spit it back out, but I forced myself to take a few more sips until I got used to the taste.

Over the course of the next couple hours, I mingled with different groups of people I knew. I was never a hugely popular kid, but most people liked me okay. Everybody at the party was pushing each other to drink more and more, and I got pressured to take a couple shots and chug my beer.

As the night wore on, I was definitely feeling pretty tipsy. As I stumbled around from group to group, I suddenly found myself next to Jenny and a group of her friends. "Hey, Lucas, having fun?" she said to me.

"Uh, yeah, great party, Jenny," I said, my words slurring a little. Everybody chuckled.

Jenny turned to face me, and the rest of her friends formed their own circle. "So, Lucas, what are you up to after graduation?" she asked me, sipping her drink.

I told her the name of the elite private university I was going to be attending, and she looked impressed, which made me excited. "Wow," Jenny said, "that's great, congratulations!"

"Yeah, thanks," I said.

She told me that she would be going to the nearby public university. "It's not as good of a school as where you're going, although it'll be a lot less expensive," she said.

"Oh, uh, yeah," I said, leaning against the wall. "My dad is, um, pretty rich though, so we can afford it thankfully."

Again, Jenny looked impressed, which made me stand a little taller, if a little wobbly. "Oh, that's good," she said. "Must be nice having a rich dad."

"Uh, yeah," I said, not trying to sound like a jerk. "He even set up a credit card for me for my graduation present, which is nice." I wasn't sure it was a good idea to say that, but my head was swimming and I thought it might impress Jenny.

It seemed to work. "Oh, wow, that's so cool," she said. She actually took a step closer to me, away from her friends. "Um, ya know, I feel bad that we didn't hang out more these past few years, Lucas," she said.

I took a sip of my beer. "Oh, uh, that's okay," I said awkwardly.

"No, no, I was too stuck up and refused to hang out with any guys who weren't, ya know, super hot or whatever," she said. She must have been a little drunk herself. But then she said, "We should definitely hang out more this summer!"

I was so excited. "Yeah, definitely, I'd love to hang out with you, Jenny," I said.

She giggled. "You're cute," she said, and I felt myself blush. "Um, maybe this week we could, like, go to the mall together or something?"

I didn't really like going shopping, but if it meant hanging out with Jenny, it was okay with me. "Yeah, that sounds great," I said.

By this time, the crowd started thinning out - a lot of people had gone to hang out upstairs, or in Jenny's back yard. Jenny kept talking to me! Eventually, just a few of us were left in the living room - a couple of Jenny's best girlfriends, Emily and Riley, and three guys from the football team, Steve, Kevin, and Andrew. Emily and Kevin were sitting on the couch together making out, while Riley, Steve, and Andrew were talking to each other.

"So, Lucas, can we exchange phone numbers?" Jenny asked, pulling her phone out.

"Oh, yeah, good idea," I said.

I pulled my phone out. As we exchanged numbers, Steve walked over and casually threw his arm around Jenny's shoulders, sipping a beer. "Hey, man, what's up?" he said to me, smiling.

"Uh, hey, Steve," I said.

"You two having a good time?" he asked.

"Yeah, it's been really great getting to know Lucas," Jenny said, taking a drink from her cup. "Uh oh," she said, "I need another drink. Lucas, would you mind getting me another beer?" She held her empty cup out to me.

"Oh, sure," I said, eager to be helpful for her. As I walked into the kitchen, I saw Steve gently lead Jenny to the couch where Emily and Kevin were making out. They sat down next to each other.

In the kitchen, I poured a can of beer into Jenny's cup. I was a little miffed at Steve intruding into our conversation, but I was still feeling good - the attention Jenny had been showing me and the date that we had arranged made me think she maybe even wanted me to spend the night with her!

When I walked back out into the living room, I froze. There was Jenny, straddling Steve on the couch and making out with him. Meanwhile, Kevin had his hand up Emily's skirt next to them, and I saw Andrew pushing Riley up against a wall and making out with her. I just stood there, stunned at this sudden turn of events.

Awkwardly, I slowly walked over to the couch next to Jenny and Steve, standing slightly behind the couch so that Jenny was facing me. Steve was firmly grasping Jenny's butt. To my astonishment, Jenny started pulling Steve's tank top up. Their lips parted so that she could pull it over his head. As she did, she finally noticed me standing there with her beer.

"Oh, thanks, Lucas, you're so sweet," she said, taking the cup from my hand and taking a sip.

"Yeah, thanks, man," Steve said, taking the cup from Jenny's hand and chugging it all down in about five seconds. He crushed the cup in his hand and threw it behind him, grinning at Jenny.

"Hey!" she said, giving him a playful shove, but then she just started making out with him again, running her hands all over his muscular chest and abs.

Steve parted lips with her again and turned to look at me. "Hey, since you've been sooo sweet, Jenny wants to give you a little present," he said.

"Huh?" Jenny said, confused. As she did, Steve's hand quickly moved up and, in one easy movement, he untied the string of Jenny's bikini top. It fell off of her, revealing a pair of amazing, perfectly perky breasts.

Everybody there saw and started laughing. Jenny was laughing too, even as she covered herself with her hands. Then Steve's hands slid up her body and replaced hers as he squeezed her boobs and kissed her. He then brought his mouth down and started sucking on her left breast.

Jenny giggled as I watched. I was stunned. At the sight of her bare breasts, I had immediately gotten hard, and my erection pressed against my jeans. But I was also so embarrassed at Steve having just swooped in and taken this girl away from me in a matter of minutes.

As Steve went back and forth licking and kissing Jenny's breasts, Jenny said, "Um, thanks for coming, Lucas. I'll, uh-mmmm," she said, interrupting herself with a moan, "-I'll see you next week, right?"

"Uh, yeah, see you," I said. "Have a good night."

"She will," Steve said and laughed.

As I walked to the front door, the others called out "Bye, Lucas" or "Good night, Lucas," laughing a little as they did.

I was so humiliated, but also so turned on at what I had seen. As soon as I got home, I immediately went to bed and started masturbating, images of the hot sex Jenny and Steve were probably having running through my mind.

***

The next day I texted Jenny: "Had a great time at the party, thanks for inviting me! When would you like to go to the mall with me?"

Sure, I had been embarrassed when Jenny ended the night with Steve, leaving me standing there to watch, but I still felt encouraged by how much attention she had given me and how she wanted to go out with me.

She texted back, saying she had a great time too. We set up our date for later that week!

The day arrived, and that afternoon I drove over to her place to pick her up. She jogged down her driveway, wearing a short, blue sundress. It fit her top tightly, showing off her figure and revealing some cleavage, and then it was a little more flowy at the bottom. At one point the wind briefly blew the bottom of her dress up and I caught a glimpse of the pink thong she was wearing.

When she got in the car she leaned over and gave me a peck on the cheek. I was practically in heaven. We headed to the mall, making small talk on the way.

When we got there, she led me around from store to store. I was perfectly happy following her where she wanted to go, as I had no real interest in shopping anyway. It also allowed me to see her try on all kinds of different hot outfits. I would stand outside her dressing room and she would model different things for me. It was especially great when she tried on things like skirts or shorts, because she would be completely topless when she modeled them, opening the door to the dressing room and letting me take a peek. She always looked so hot, and I had a hard-on pretty much the entire time we were shopping.

When she found something she liked, she would kind of shyly ask me if she could put it on my credit card, saying she didn't have enough money to buy anything for herself. I felt a little weird about it, but I wanted to impress her and make her think I was nice, and I definitely didn't want to do anything to keep our relationship from developing. And besides, I could afford it. By the end of the afternoon, I had ended up spending almost $1000 on her.

When she had finally tired of shopping, we walked through the parking lot to my car. I was carrying all of the bags of clothes I had bought for her - I wanted to be a gentleman, after all - while she checked her makeup with the camera on her phone.

When we got in the car, I turned to her and said, "So, um, would you maybe like to get dinner with me?"

She smiled and said, "Yeah, that sounds great! Um, have you heard about that new Italian place that opened up?"

"Oh, yeah," I said. "It's supposed to be really fancy, right?"

"Yeah..." she said. "I understand if it's too expensive, I just thought it would be nice."

"Oh, uh, no, it sounds great, let's do it," I said eagerly, not wanting to mess up our date.

"Great!" she said, excited.

We arrived at the restaurant and they quickly sat us. I felt a little uncomfortable in such a fancy place, but I could see that Jenny was having a great time. Our waiter was a very handsome Italian-looking guy, probably about 25 years old. As he handed us our menus, he said to me, "I hope you do not mind my saying so, sir, but your date is a truly stunning beauty." He smiled down at Jenny, who giggled shyly and thanked him.

"May I get you something to drink?" he asked.

"How about a bottle of wine?" she asked me. I was a little stunned - we were underage and he was definitely going to card us.

"Um, uh, I don't really know anything about wine," I said awkwardly.

"Oh, that's quite all right, sir, I will pick out a bottle that I think the young lady will enjoy a great deal," the waiter said, talking to me but looking at her.

"Oh...uh...okay," I said. She smiled up at him.

The dinner continued, and we had a good time talking to each other. She ordered the most expensive item on the menu, but at this point I didn't care. I had never had wine before and it tasted terrible to me, but she really loved it.

After the dinner course, the waiter approached again and said, "Might I recommend the tiramisu for dessert?"

I was pretty full from dinner and didn't really want to spend any more money, but before I could say anything, Jenny said, "Oh, that sounds great!"

"Excellent," the waiter said.

Jenny then started rising up out of her seat and asked the waiter, "Could you let me know where the ladies' room is?"

"Of course, miss, allow me to show you the way," the waiter said.

I watched as he walked her across the room and down a hallway. As they walked, he placed his hand gently on her lower back, which seemed a little weird to me, but she didn't seem to mind.

I sat and waited for her to return. And sat...and sat...and sat. Five, ten, fifteen minutes passed. The entire time, I saw no sign of our waiter either. I started to get both worried and annoyed. Finally, I saw both of them emerge from the hallway and back into the main room we were in. He broke off from her to go to the bar as she made her way back across the room to our table.

As she sat down, she looked a little flush and her hair was slightly messed up. "Everything okay?" I asked, concerned.

"Oh, yeah, of course," she said, smiling. "Just took a little while freshening up. You know how girls can be." She laughed.

"Uh, yeah," I said. Something seemed off.

The waiter came over with the dessert, along with a couple cocktails.

"Here you are," he said, placing the drinks on our table. "In appreciation for being such wonderful guests, please enjoy these cocktails on the house." He put the drink directly in Jenny's hand, and they both held onto it for a moment, their fingers touching, as he leaned in toward Jenny and, smiling, said, "Please come back anytime."

She giggled. "I will, thank you so much," she said.

I definitely felt like I was missing something, but any concerns I had left my mind as our conversation continued over dessert. As she ate, she said to me, "Um, Lucas, this might seem a little sudden, but..."

She trailed off. "What is it?" I said, intrigued.

"Well...I know you're heading off for college in the fall, but, I've had a really good time today, and I was wondering if you maybe wanted to be, like, my boyfriend for the summer?" she said.

I was stunned and thrilled. It was like a dream coming true! The most beautiful girl in the school wanted to be my girlfriend! I couldn't believe it. "Um, uh, wow, yes, Jenny, I would love that," I said, stammering.

She giggled at my awkwardness and said, "Oh, great, I was worried you'd say no, since, ya know, I don't have a lot of money and I'm not as smart as you or anything."

"Oh, Jenny, uh, I don't care about that stuff," I said, "I think you're great and I'm so excited to be your boyfriend."

We finished the dessert, and I paid the bill (which was several hundred dollars - the waiter had picked out a really expensive bottle of wine!). In the car, I turned to her and said, "Um, so, what do you wanna do now?" I was kind of hoping she would suggest going back to her place.

"Um, well, some of my friends are at this bar where we know the owner and he lets us drink, I'd love to go meet up with them and give them the good news about our relationship," Jenny said.

I didn't really want to stay out, but I also didn't want to seem like a jerk, so I just said, "Yeah, sounds great," and let her direct me to the bar.

Being a weeknight, the bar was pretty empty except for Jenny's friends - Steve, Kevin, Andrew, Emily, and Riley were all there, along with a few others. We greeted everybody, and then Jenny said, "So, guys, I have some good news. Lucas has agreed to be my summer boyfriend!"

I thought this announcement might be a little awkward for Steve, given his clear history with Jenny, but he cheered along with everybody else. It felt bizarre being included in this group of people who had always been the cool kids and had never hung out with me, but I was so happy. I placed my arm gently around Jenny's side and she looked over and smiled at me.

"Celebration shots!" Emily called out. Soon enough, we were all downing shots of tequila. I declined mine, saying I had to stay sober to drive Jenny home. I felt a little lame, but Jenny just thanked me for being so responsible. Then somebody put some music on and we all started dancing.

I wasn't a great dancer, and after a little while I got tired and decided to go sit at the bar. I was hoping Jenny would come with me, but she stayed out on the dance floor with everybody else. She wasn't dancing with anybody in particular, but I saw all the guys grinding on her at different times in a way that made me feel a little uncomfortable given that we were dating now.

I was starting to get really tired, and Jenny was starting to get really drunk. At one point, she stumbled and fell into Kevin's arms. Kevin was the most popular guy in the school, the football team's quarterback and a real all-American looking guy. As he grabbed her to hold her up, I saw him copping a little bit of a feel. I got upset, but didn't want to make a scene or anything.

Kevin put his arm around Jenny and walked her over to the bar where I was sitting. She was clearly stumbling. "Hey, man, I think maybe it's time for you to take Jenny home," Kevin said.

"Uh, yeah, looks like it," I agreed.

"I think maybe I should come along so that I can, ya know, make sure she's okay, since you'll be busy driving," he said.

"Oh, um, you think that's necessary?" I said.

"Um, yeah, man, look at her, I think it's the considerate thing to do," Kevin said, acting a little disgusted by the question.