Cuckold Beginnings Pt 02 1

Waking up the next morning felt like I was getting up from the best dream ever. I checked my phone and it was around 9am. I didn't even know what to do. I walked out into the common area to get some cereal and my roommate that was there the night prior was on the couch. Without saying a word he got up and gave me a bro hug. He knew something good had gone down.

I wanted to see Ashley right then. I texted her, "Good morning..."

She replied almost immediately, "Those are some ominous dots... Also, good morning. :)"

I sent a "haha" and a quick "Last night was..." (Yes I'm aware what a loser I was texting like that but I was young).

She replied quickly again, "A mistake. I know. I can't believe we let that happen."

I was pretty sure she was kidding but a little part of me did panic for a second. She text again, "...I'm kidding. It was a great night."

I just replied, "One of the best." She sent a smiley face and we had a lull of a couple of minutes.

I finally said, "So, what now?"

She said, "I think I take you out tonight, my treat." She continued, "Then you eat me out again like you did last night. Sorry if I woke the roomies." I was so turned on again with just how forward and sexual she was with me. She had always been so classy and untouchable then here we were.

I didn't respond for a second then said, "I want to do that right now. Lol"

She laughed and said I was really good at it. I told her it was my first time doing it. She replied, "Are you kidding!? You're a natural..." We made our plans for that night.

I picked her up and drove us where she had picked out for us. She was dressed unbelievably sexy. A little black dress that was cut up her leg. It felt fancy but she promised it wasn't. She has flats on. I can remember it like it was yesterday.

We get to the bar and we get a little table. She sits across from me. I spent the next two hours falling in love. She made everything easy. Every guy in the place caught a glimpse of her when they walked by. I felt like the king of the world sitting across from her.

Afterward we walked down the street in our little college town and I actually held her hand. It was all happening so fast but we both knew it felt right. Looking back, life didn't get much better than young love in the middle of our period of self discovery in college.

Every single guy that walked by looked at her. Even the ones walking with their girlfriends. I finally said something. "You realize that every single guy we've seen has been checking you out." She said she didn't think so and I said, "Oh yeah? Watch." Next guy walked by and she looked at him and saw him check her out.

"See!?" I told her.

She laughed and said, "It's the dress... It doesn't make you jealous does it?"

"Hell no," I said. "I am the one getting to hold your hand and walk with you."

"That is true. You like other guys wanting me, huh?"

I shrugged and said, "Yeah, I guess so."

We walked for as long as we could in the town and since it was a Saturday night we had a lot of options. There was a pretty "happening" place nearby that was a bar but also had dancing, which got crazier as the night went on. She suggested we go check it out.

As we walked in I looked around and couldn't believe there could be that many frat bros in one place. There were plenty of sorority girls for them to mix with though. Again, I just see head after head turn and check Ashley out. We had a couple of more drinks and did some dancing. I'm not a good dancer and she's just a fun dancer. It was sexy as hell just because of who she is and how she moves on the floor.

I kept wanting to grind on her but I felt awkward for some reason. We had a lot of fun awkwardly dancing with each other though. So many laughs. I finally had to go to the restroom. As I came back to the dance floor I couldn't find her for a second then I saw a very good looking guy with his hand on her hip and grinding against her ass just a little.

My heart fucking sank. I immediately thought "what the hell is she doing?" I then watched her for a second and realized how fucking sexy she looked dropping her ass right into him. She saw me and waved. Then turned around and said something right in the guy's ear and left him to come over to me. I saw him watching us. She said, "That guy will be thinking about that all night and you get to take me home."

I didn't know what else to do so I basically mauled her and kissed her right there on the dance floor. She laughed and pushed me off a little. I could barely hear her at this point but I heard her say, "Thought you'd like that."

We kept dancing for a while and then went back to the bar area. That guy was there and Ashley went up next to him and I followed. He looked over and she said hey but we ordered our drinks. You could tell he was sad and she looked at me and said, "Now I feel a little bad for him." I was basically yelling it was so loud and I said,

"No you don't." She laughed very hard.

I never expected her to be such a tease but it was so sexy. I was more and more intoxicated by this confident and sexual woman.

We finally went outside and were super sweaty after the dancing and drinks in such a small space. We walked back towards my car and she said, "Can I ask you something?" I of course told her yes and she said, "Since that was your first time going down on a woman, does that mean you've never had sex either? It's really ok, just curious."

I told her I'd had sex with one of my girlfriends, who she actually knew, but only a few times. I told her it'd been hand jobs, a bad attempt at a blowjob one time, and me finishing myself most of the time.

She leaned her head against me and said, "Oh you poor thing..." I didn't know what to ask her but I was curious how experienced she was. I was getting the feeling it was very experienced, which was turning me on for some reason.

I finally thought of the way to ask. I asked when she lost her virginity. She said when she was 18, so two years prior. It was with a guy who had dated one of her friends for a while who she had a massive crush on. Her friend broke up with him when she went away to another college so that summer she fucked him a lot until he left and went to a different college. She told me this story and I could tell she watched my face.

"Does it bother you hearing that?" I said it didn't at all but I left out the part where I didn't know why I enjoyed hearing it. I wanted to hear more.

"When you say 'hooked up a lot' what does that mean?"

She blushed a little and said, "So you really want to hear this?"

"Just curious, like you were about me." For a second I could tell she was trying to figure out if I was judging her so I cut that thought off. "Zero judgement. I just want to know you."

She kissed me and then said, "Well, it was about a three week fling we had before he left and we were together almost every day. I guess he had had some feelings about me as well and it was good to get it out of his system." I was so jealous. She turned and looked at me. "What's going through your head?" I really didn't know and I told her that.

We got in my car and went back to her place. It was late. Around 12. She told me she'd understand if I was tired and just wanted to go home. I looked at her and said, "A gentlemen never leaves a woman hanging, especially after she paid for the evening." She loved that and we went inside and I ended up eating her out. She put a pillow over her face this time.

I could tell she was exhausted and didn't want to ask her for anything. I told her I had an amazing night and she said, "Hey, I will take care of you." I guess I was being gentlemanly but now I wonder what the hell I was thinking when I told her not to worry about me and to get some rest. She gave me a huge hug and said she had a great time.

When I got home I furiously masturbated for about the 20 seconds it took for me to cum with all of what had transpired in my head.

There were times I wondered if she had some issues of some sort with how much she loved teasing me and other guys. I mentioned it a little to a friend of mine and he said, "Brother, there are far worse things in this world than a woman who knows and loves her sexuality."

Changed my life.