My first year of school was over, and I was home for summer break. I went to visit my friend Johnny to catch up and have a few beers and a few laughs. He had decided not to go to school but was working as a delivery driver for a food distributor. Johnny looked as fit as ever and was sporting some facial hair for the first time in his life.
“How were the girls at your college? Were they easy?” Johnny said, getting to the point.
“They do love to party a lot. I got head anytime that I wanted it,” I said, making it seem like I was more successful sexually than I really had been.
“How about you? Any new conquests to talk about?”
“I was dating this woman who had a kid, but she moved back to Florida, and we lost touch. Other than that, just sex with some club girls.”
“Nobody from high school,” I said, recalling some of his memorable conquests.
“No. I talked with a few of them off and on, but I never saw them.”
“You definitely had your pick of who you wanted.”
“I still do.”
“I bet you have even more to choose from now.”
“That’s for sure.”
He surprised me when he told me the best lay that he had in high college was this girl named Cindy. I wondered he was lying to me, or just joking with me. The reason I was surprised was because Cindy was not very famous and had a rather plain and oblong face in spite of having a hot body and sexy persona. Really, believing that she sucked at sex because she was plain looking is a horrible and naive way to think. At the time, I just figured that the prettier girls I knew he had fucked were naturally better in bed, but he told me different.
“What about Olivia?” I said, wanting to better figure out his choice of Cindy as being his best sex in high college.
“She was no fun. She was so self-conscious about her flat chest and wouldn’t let me even see her tits or touch them. I want to forget her,” Johnny said, disparaging a very hot looking Latina that no guy in college would have passed up.
“What about Jennie? Her body was amazing.”
“I did all the work; she didn’t move at all. Yeah, her legs were something else, but she was frozen the whole time I had her on my bed.”
“All she wanted to do was kiss; she acted like my dick wasn’t even in her while I was fuckin’ her.”
“So, Cindy was the best,” I said, conceding.
“Yeah, she was the first to wrap her legs around me while I fucked her. It was like she fucked me just as much. That was a first for me,” Johnny said, passing me a bottle of beer.
“What happened to her?” I said, regretting that I had overlooked someone who had flirted with me a few times.
“She went away to college with her friend Breanna. She called me a couple of days ago, but I was working and never got back with her.”
“Did you ever get with Breanna?” I said, recalling a bossy girl with a great ass.
“No. I tried, but she wasn’t into me,” Johnny said, admitting he couldn’t fuck them all.
“That’s surprising. I thought she would have been part of a package deal with Cindy since they were such good friends.”
“Maybe you should give Breanna a call,” Johnny said, thinking I wanted to hook-up with Breanna, when it was really Cindy I wanted to try to be with.
“I’d rather try to get with Cindy if you don’t mind,” I said, not caring if he knew I suddenly needed resolution with his former lover.
“No, I don’t mind. She’ll be quite the experience if you can manage it. Thinking back on it, she was the one that came after me. I’ll give you her phone number.”
“I’m sure it’ll be fun for you, no matter what happens.”
There was that level of comfort that comes from seeing an old friend, but there was also the opportunity to make up for something I missed during high college: an opportunity with Cindy. Johnny gave me her number, and I dialed it while he was on the phone with some other girl. It was so strange hearing Cindy’s voice; I almost hung the phone up out of fear of rejection, but I decided to risk it.
“Hi, Cindy, this is Will from high school,” I said, knowing she’d remember me.
“Will! I missed you so much!” Cindy said, sounding friendly and a little drunk.
“I’m at Johnny’s house, and I asked him for your cell phone number.”
“Cool! We should hang out before we have to go back to school. You’re going to school out of state, right?”
“Yeah, we need to do that.”
“What’s Johnny doing?”
“He’s on the phone.”
“Of course, he is. With one of his bitches, I’m sure.”
“You know, he’s so small,” Cindy said, lowering her voice like she was telling me a secret.
“Really?” I said, looking over to Johnny, who was talking on his phone but looking at me.
“Yeah, the smallest I ever had.”
The rumor was that Johnny was small when it came to the size of his cock, but never saw him naked, so I really didn’t know how much truth there was to it. I did like that my conversation with Cindy had taken that somewhat private turn, even though it was at the expense of my friend. I wanted to tell her that Johnny raved about how good she was, placing her at the top of his high college sexual partners, but I was looking for the right moment to do it.
We talked a little more about how our first year of school had gone and about how our summer jobs were going. She was working as a lifeguard at a neighborhood pool, and I was working at a sports complex setting up basketball and soccer events. When she had said that she was a lifeguard, I told her that I wanted to see her in her outfit.
“I’ve got a wedgie most of the time, and it’s hot all day. I’m really not having any fun,” Cindy said, sounding miserable.
“Still, I bet you look hot,” I said, imagining her shapely ass with a wedgie.
“You’ll have to come by and see for yourself.”
“I will,” I said excitedly.
“I can wait to see you. It’s been too long,” Cindy said, making me think she was also excited.
After I hung up with Cindy, Johnny finished his conversation, too. I wondered he was gonna ask me what I had talked about with his ex-lover, but he acted like he was not interested in hearing about her. We had a few more beers before he was off on a date with some girl he had met while making his deliveries. He wished me luck with Cindy, and said she was worth it at least once.
It was during my lunch break that Cindy sent me a picture of her face with text that said: Guess what I have on? She looked pretty, and like how I remembered her, but her hair was styled with a more sophisticated cut. I told her she was looking hot, even though I could not see the rest of her. She said she would think about sending me another picture.
We made plans for me to visit her on her lunch break the following day, while I would be on a short break from my work. I was excited to see her but was thinking that maybe Johnny had oversold her abilities, and she was not so special in bed. It didn’t matter, I was gonna make the best of it with Cindy, knowing that I was going back to college soon enough.
While I was on my way to see her, Cindy sent me another picture. This time, she was standing next to the pool and showed me her face and torso. Her boobs looked average-sized, maybe a C cup at most. I hurried to get to her, partly because I wanted to see her, but also because my break from work was not that long.
Her last text said that she would be waiting for me at a picnic table on the north side of the pool. I spotted someone sitting alone at a table and headed straight for them. It was her! She stood up and greeted me with a hug and a kiss on the lips. Cindy had on her lifeguard uniform, but she was wearing shorts.
“Wow! It’s been so long,” I said, happy to see her.
“You’re one of the few classmates that I really missed. We really had some great times in biology,” she said, reminding me of when she occasionally sat next to me braless.
It was hot, and she looked uncomfortable but, seeing her with her hair up and looking a little flustered, was sort of sexy, I wondered. My only complaint was that she was wearing shorts over her swimsuit. I had wanted to see her ass with a wedgie, but I had to settle for her ass covered up instead.
“You said Breanna works here, too,” I said, trying to begin the conversation with Cindy.
“Yeah, she’s around here somewhere,” Cindy said, glancing around.
“It sounded like you had fun your first year away at school.”
“I did. There was one incident, though, that scared me a little and still worries me,” she said, looking pensively at the pool.
“Is it too personal?” I said, curiously.
“It is, but I’ll tell you anyway.”
“I don’t want you to tell me about it unless you’re sure you want to.”
“It’s okay. I kind of want your opinion afterwards.”
“Sure,” I said, agreeably.
Cindy adjusted herself in her seat and crossed her long legs; her foot, especially the nail in her big toe, made contact with my bare calf. I liked the contact with her; it was different from our hug and kiss had been, but it was still a body part of hers reaching out to me.
“I had gone to a few parties without anything strange happening. Yeah, there were some hook-ups, but nothing out of the ordinary,” she said, blushing some.
“Frats?” I said, interested in her story.
“And the incident?”
“It was also at a frat. I remember going there, talking to a few guys, but then it all gets hazy.”
“Yeah, I was probably drugged. I woke up in the back of a pick-up truck, on the flat bed. I just went to my dorm after I gathered my stuff.”
“That is scary.’
“Yeah, but the craziest thing was that my asshole hurt. I had never been penetrated there, but I think someone did something to me anally,” she said, trying to keep her composure.
“That’s so wrong.”
My break was coming to an end, but I felt uncomfortable about leaving Cindy after she told me that. I felt bad that she may have been penetrated anally without her consent. Plus, she complained about having a wedgie all day. I was sure she needed some looking after in her back regions.
“You wanted my comment on what happened?” I said, feeling as though I were prying.
“Sort of. I know you have to go soon, and I have to get back to the pool. I’ll make it quick,” Cindy said, wanting to get to the point of our meeting.
“I don’t know if I would have enjoyed what happened to me, but not remembering anything makes me feel like I missed out. I want to try it with someone I trust. Will, I trust you.”
“What about Johnny?” I said, standing up.
“I trust him, but I sort of want to move on from him. Plus, he really is small. I want to feel something.”
“What if I’m small, too?”
“Then, the jokes on me.”
“Okay, I am glad you trust me. No, I am not small,” I said, kissing her goodbye.
Finally, she sent me a picture that showed her in her swimsuit without the shorts. Her ass looked full and firm; her hips were curvy and ultra-feminine. She was standing with Breanna, her dark-haired counterpart that was also her oldest friend. I told her that seeing her wedgie would be nice, but she looked amazing either way. She asked me how she compared to Breanna, wanting to know who I thought was sexier. I told Cindy that it was close, but that her curvier body made her the choice for my tastes. I worried that she might say something about their faces, knowing that Breanna was prettier, and Cindy would know I was lying if I picked her over Breanna, but she let it go.
What Johnny had said — that Cindy was his top pick of all the girls he had sex with during high school — was still pressing on me, and I needed to talk to her about it, needing to know what she thought of his declaration. I didn’t want to tell her in a text, so I called her instead.
“Guess what I just did,” Cindy said, sounding excited.
“Rescued somebody at the pool?” I said, clueless.
“No. I’m home now. I just put an anal plug in my butt!”
“That sounds so hot,” I said, imagining her doing that.
“Getting it ready for you.”
“I can not wait for that.”
“I want that so badly!”
“Cindy, the reason I called you is to tell you something Johnny told me. It made me so hot for you when he told me,” I said, wanting Cindy to know Johnny’s truth.
“What? That he liked my body?”
“No. Of course, he liked it a lot, but he said that you were the best sex that he had in high college. He said you were better than all the other girls he had sex with,” I said, thinking she would be glad to hear that.
“I’m not surprised. I asked him about Olivia once, and he said she kept her top on the whole time,” she said confidently.
“He really raved about you.”
“He wanted me to have a threesome with Billie and him, to see who had the better body, but she was scared to.”
“Wow! That would have been amazing,” I said, trying to picture Cindy and Billie naked.
“Enough about Johnny and his bitches. This is about my ass. Are you with me on this?” she said, slightly ruining the moment for me.
“Yes, I’m with you.”
The next few days were about finding some privacy for Cindy and me to find out if anal sex was something that she could truly like, or, if I liked penetrating that region. My parent’s house was an option early in the day, but she said she preferred the nighttime for sex. Her parent’s house was not an option. I suggested that we go to Johnny’s house, but she shot that down right away. The only opportunity would come at her friend Breanna’s place. Her parents were going out of town the following weekend. With summer going quickly, we agreed on her best friend’s bedroom.
When I got there, I was greeted by Breanna. She acted like she wanted to give me a hug but didn’t. She looked better than in high school. Her short hair gave her an even bitchier appearance than with the longer cut I last knew her to have, making her seem combative almost, but she smiled warmly at me.
“Hey, Breanna,” I said, almost reaching out to touch her.
“Hi, Will, come in,” Breanna said, smirking.
“How are you?”
“Good. Your girl is waiting for you upstairs. Second door on the right,” Breanna said, pointing up the stairs.
“Okay,” I said, seemingly ready to do my duty for Cindy, but thinking Breanna was worthy of my time, too.
“Go! What are you waiting for?”
“Your haircut makes you look so hot,” I said, wondering if Breanna was the better choice.
“What would Cindy say?”
“I don’t think she’d care.”
“Just go upstairs. Maybe we’ll talk later,” Breanna said, dismissing me.
Going up the stairs, I started to wonder if Cindy and I had even the slightest chance to make our bedroom rendezvous work. Was she really inclined for this, and was I ready for it on my end? I kept thinking of Breanna, wanting to go back down the stairs to declare my willingness to be with her. Nonetheless, I found the second door on the right and knocked on it.
“Come in,” Cindy said from inside Breanna’s bedroom.
There was Cindy, in the middle of the room, standing with her hands on her hips. She was wearing a blue robe that was about knee-high, and she was barefoot. Cindy’s hair was in a bun, and she looked a little nervous. I met her in the middle of the room and kissed her, but she moved her lips away quickly. I sensed I was there for only one thing: the use of my cock in her ass.
“You look gorgeous,” I said, exaggerating her level of facial beauty.
“Thank you,” she said, looking away from me.
One of us had to take the lead; I sensed that she was getting nervous. As excited as I was to take her ass, I would have been fine with her pussy. I took hold of the belt on her robe and tugged on it, revealing her naked lower half and the black bra she was wearing. Her vagina had a triangular swath of neatly trimmed brown hair. Cindy didn’t say anything, seeming relieved that I had started things off for us.
“Is your plug in?” I asked, kissing her softly and reaching down to her ass.
“Yes!” She said, perking up.
My hand found something that felt like metal inside her, firmly in place and widening her for me. Her blue eyes gave off a warm vibe now, letting me know that she was composed and ready for what awaited us. I tried to give off a confident vibe of my own to allay her fears.
“Wait until I am ready for you before you pull out my plug,” she said, putting her hand on my ass.
“Whatever you need, baby,” I said, kissing her again and feeling her ass.
“Today, I am your baby,” she said, taking off her robe.
I leaned down and kissed the top of her boobs that were exposed with her bra still on, and I held her ass as if we had been longtime lovers used to each other’s bodies. We kissed for real this time, abandoning any anxiety the moment may have supplied earlier. It felt as though we were coupled and meant for one another without having a clue as to what made the other tick.
“Over by the mirror, on the yoga mat,” she said, pointing to the full-length mirror on the wall directly across the bed.
“Perfect!’ I said, pinching a nipple that looked erect under her bra.
“Hey, this is only about my ass. I don’t want you getting distracted,” she said, turning to walk over to the yoga mat, letting me see her shapely rear with the added feature of a silver-colored anal plug.
Cindy was ready to start, shaking her ass at me as an incentive to get ready myself. She didn’t need to sell me on the idea because I showed up to get my distribute of some Cindy. The distribute that Johnny had either not considered or not found appealing. She lowered herself onto the mat, offering her unguarded rear hole to me.
The next step was for me to take off my pants, bringing out the tool needed for the job of penetrating Cindy. I could see her looking in the mirror, sizing me up. The mirror made her face appear even more oblong. She watched me as I stroked my cock, lengthening it out to its full potential.
“I hope I can handle that,” Cindy said, focused on my penis.
“Any lube?” I said, looking at her face in the mirror, attracted to her even more.
“I am lubed up now, but here is some for you,” she said, tossing a small bottle of lube onto the mat.”
The lubricant felt cold when I sprayed it on my dick. I could see that she was watching my every move, anticipating the moment I would relieve her of the anal plug. Finally, I placed a hand on her ass and caressed her ample cheeks, letting her know it was mine now. Working my way to the steely piece fitted tightly in her anus felt like the official transference of her from Johnny to me.
Slowly and gently, I slipped out the plug and set it to the side of the yoga mat. There was some gaping, but I needed to take advantage of the opening before it closed. With her keen, blue eyes tracking me, I introduced the tip of my penis to her pink orifice and nudged it in some. We had just linked up, tethering ourselves to a moment of truth.
“Is it in?” Cindy said, disrupting the silence.
“Barely,” I said, pushing in a little more.
“Relax,” I said, kissing her smooth back.
After a few more pushes to get in, it felt as if she suddenly started to squeeze me, either from tension or just the limited space. Cindy moaned, but since she was in no real pain, she started to push her hips a little in my direction. These were minimal pushes, possibly even caused by vanity. I accepted them, happy that everything was going smoothly so far.
We locked eyes in the mirror, trying to balance what I was making her feel with what we wanted to feel, I thought. She looked scared one moment, then looked revitalized the next. I decided, rather sadistically, that I was going to make her regret going after Johnny instead of me. I started to pump her ass a little harder, pushing her limits further.
“I can really feel you now,” Cindy said, liking the change of pace.
“You look so gorgeous, taking it from me,” I said, staring at her asymmetrical facial features and liking that aspect of her so much.