Curious how it feels

I left that morning. In the afternoon, I received a text from Carol.

Carol: My roommate told me she saw you naked last night

Me: Did you tell her we just had sex?

Carol: No way! I apologized and said I will tell him he has to keep his clothes on

Me: She probably thought I was jacking off in the kitchen. Sorry your roommate thinks I’m a creep

Carol: She wants me to set her up with you…without going into detail she really liked what she saw

Her roommate wasn’t the most outgoing girl. She mostly stayed in her room. She never went out with us. She always wore a hoodie and sweatpants when I saw her. But she was relaxing at home, so I couldn’t hold that against her. I texted Carol to give her roommate my number.

So I texted with the roommate. Her name was Haley. She was pretty nerdy and was a chemistry major. I kept it flirty but I never brought up being naked in the kitchen. We made plans to go out the next time I came up to her town. It wasn’t going to be a traditional one on one date. We were going out with Carol’s crew for a birthday celebration.

My memory of Haley was on her in glasses with her blonde hair up in a ponytail, wearing a hoodie and baggy sweatpants. I didn’t even recognize her when she came out of her room. Her blonde hair curled to her shoulders. Her blue eyes no longer blocked by frames. Her dress showed off her body and her unexpected cleavage. I had hit the lottery.

She saw the dumbfound look on my face and said, “I don’t always wear sweatpants. You’ve only seen me on the weekends when I’m either going to bed or getting up from bed.”

Carol whistled when she saw her roommate, “You’re looking hot Haley. I you sure you want to go out with Chandler? You’re way out of his league.”

Haley looked me over. She said, “It’s okay. I feel like slumming tonight.”

We pre-game at the apartment before going to the bar where the birthday part was happening. After the first shot, Haley said, “You need to look after me. I don’t really drink much.”

I told her to drink half as much as Carol. I didn’t want to take care of a vomiting college girl all night. We went out. Haley was immediately all over me. I tried to hold her hand and she took it and put it around her shoulder. She said, “I’m your lady for the night.”

So we didn’t treat it like a date, that night we acted like we were already a couple. It took some of the awkwardness away. It felt natural to put my hand on her ass while standing behind her.

While dancing, she said, “Let’s leave now, so we can have some time alone together in the apartment wink wink.”

The **** from the night had loosened me up. I finally decided to see if I could bring up the elephant in the room. I asked, “So why did you ask Carol to set us up? You’ve never really interacted with me before.”

“Well I never knew if you and Carol were a thing,” she said. “I didn’t want to be a third wheel. But I talked to Carol and she was very, very adamant that you were not a thing.”

I laughed, “How adamant?”

“Sooooooo I had told Carol that I had seen you naked,” she blushed at the memory. “And Carol acted like I was describing her brother. She gagged when I mentioned your penis.”

Carol definitely didn’t gag on my penis when she stuffed it down her throat. She was a better actor than I thought.

“You mentioned my penis to my best friend?” I feigned outrage.

“Oh shut up Chandler! How could I not mention your penis!? You didn’t even try to cover it up when you saw me!” We get to the apartment, and she unlocked the door. “It’s like you wanted me to see it!”

I push her into the apartment and kissed it. “My master plan worked.” I backed her over to the couch. We sat down on it and made out. I didn’t push too hard, but I couldn’t resist feeling up her tits. I had been staring at them the whole night.

She said, “Let’s take it to my room before Carol gets back. I wouldn’t want her to see me hooking up with her brother.”

Once her bedroom door shut, we peeled off each other’s clothes. She had a surprisingly nice body: her tits a perky handful, her stomach flat, her pussy freshly shaved. My clothes came off and she sucked my dick. It was fine at first, but once I got hard, the teeth constantly scraped my cock. I faked being into it so I didn’t kill the mood, but I didn’t let it last very long.

I had her lay back on the bed. We made out while I fingered her. I put on a condom. I put my cock to her opening and slowly pushed in. She was extremely tight. The look on her face screamed that she was in discomfort. I slowly moved the tip of my cock in and out of her. She grimaced, and said, “Ow I’m sorry. But I’m in pain.” I pulled out.

Tears welled in her eyes. She said, “I’m so sorry but I can’t. Just that little bit really hurt. I’m so sorry. Please don’t be mad at me.”

I said, “It’s okay.” I hugged her. “I don’t want to hurt you. We’re just not compatible down there. Nothing to cry over.”

She said, “I don’t want to be rude, but do you mind sleeping out on the couch. I want to be alone right now.”

I put on my clothes and left her room. I really wanted to come, but I did not want to put that on Haley. She felt bad enough. I sat on the couch for a few minutes when the door from outside opened. Carol drunkenly stumbled in.

She saw me and asked, “What’s up with you?”

I replied, “You drunk enough to fuck me?”