I started my sophomore year at college on academic probation. I had goofed off and partied a little too much my first year. Being on academic probation meant I had to meet with my guidance counselor three times a week. The first time I met Sarah, my guidance counselor, she was very critical of me. This didn't fly with me, I was cocky and brash not taking shit from anyone. I ended up walking out on our first session. I skipped the rest of our meetings that week. I got a call from Sarah that following week telling me I was required to show up.

When I showed up, Sarah apologized for being too direct and admitted she had come off like a "bitch". Our next sessions we talked more and more as to why I did so poorly in my classes. I finally fessed up and told her I skipped classes often and missed assignments...even not showing up for tests. Throughout the fall semester, Sarah opened up about herself and our meetings started going longer and longer.

It was December and my grades were looking solid before my finals. I had only two more meetings with Sarah before break. At this point, she and I had become friends... Giving each other shit in fun. We were finishing up our second to last meeting when Sarah, who was gay...it never bothered me, made the comment that if she wasn't gay " she'd rock my world". I seriously thought she was just bullshitting so I came back with "if I ace my finals, I'd hold her to it. Now to describe Sarah, she always wore very conservative long dresses and blouses covering up most of her skin. Sarah came back with let's just get a drink after finals and talk about it. I agreed.

I finished my finals, I had a couple of days left before I was going home...my roommate had already left. I met Sarah at a bar just a couple of blocks from my apartment. Sarah was dressed much different than in our meetings. She had on very tight jeans which showed off her nice round hips. She had purple top that was very low cut which surprised me how busty she was because I never really noticed before. Sarah told me when I first got there that anything that happens would get her fired from her job. I thought she was joking again and made the comment "what? Like we are going to have sex or something" Sarah reached across the table and put her hand on mine just staring at me. My cockiness disappeared. The first thing I asked was if she was serious. Sarah said it was no fluke us meeting at this bar so close to my apartment. She finished her drink and suggested we go now since she had to be home by 7pm. I slammed my beer down and we walked over to my apartment. Walking up to the second floor, I watched Sarah from behind going up the stairs. The way she moved side to side with those hips.I was excited.

I locked the door and Sarah kissed me. It wasn't too hard, he soft lips felt nice. We started removing clothes as we made our way to my bedroom. First kicking off shoes, then my shirt, Sarah's top, my jeans, then Sarah's jeans...which took some effort to get off her hips. We stumbled as I tried to take my socks off with my feet. Sarah removed her bra, her breasts were large and saggy with big puffy nipples. I pulled my underwear down,I was already erect. I leaned over Sarah as we fell onto my bed. I started to go down on her but she stopped me.Sarah rolled over on top of me. She went down on me. It was the best blowjob I ever got. She did things with her tongue, pulling tugging and playing with cock and balls. I joked asking how she knew how to do this. Sarah came back with "I wasn't gay all my life" we laughed.

Sarah moved off me and slipped out of her black panties. She was trimmed neatly down there. She got back on top of me. She grinded her pussy on me. It felt very warm. I was fondling her breasts, leaning forward to suck her nipples. The were so firm. I bit down a little too hard and Sarah asked to go easier on them since they were so sensitive. I could feel her wetness. We rolled over. Sarah reached down between us and guided me into her. She asked that I go slow. Sarah was very tight. She yelped as I pushed slowly in. I had to stop a few times so she could ready herself for more. Once in I went slow while we kissed.Sarah's hands were squeezing my ass, rubbing and even pinching it. She leaned back and we looked at each other as our pace increased. Soon I was smacking into her. Sarah was moaning loudly, I was breathing heavy. She rolled over, exposing her full figured backside to me. I wanted to go into her ass so bad but Sarah guided me into her moist pussy. I grabbed her hips firmly. Slapping hard into her. I was close. I asked if she wanted me to pull out. She just moaned and I kept going. As I unloaded my juice into her I plunged my thumb into her ass. Sarah jerked hard. I held my thumb in until my last pump of cum was in her. I took it out and Sarah flipped over. I rolled off to the side. We were both sweaty. Sarah sad I was a bad boy,referring to my thumb in her ass. I joked I couldn't resist.

We got under the covers. Sarah pulled me over and kissed me. I had my hands on her ass. She asked if I liked her ass, I told her it was perfect... She laughed. Sarah asked if I wanted to do it in her ass, I said hell yeah! She smirked and said it was a good thing she brought and enema with her. Sarah went to the bathroom and a few minutes later she returned. She handed me some strawberry scented lube. We kissed some more before she went face down into my pillows sticking her rounded ass up in the air. I poured a little down between her crack and began to lick her ass. Sarah wiggled laughing saying it tickled. I got more into it. She squirmed but she relaxed when I started rubbing her from behind. I lubed my fingers and plunged them into her. Sarah grunted, I asked if she wanted to stop but she said she'd let me know. I moved deep into her. Taking them out and spanking her. Sarah jumped from the hard slap. I rubbed the lube on myself then rubbing up against her crack. I pushed down on her ass cheeks spreading them. I tried pushing myself into her ass. Sarah seemed to be resisting. It wasn't working from behind her. I asked her to get on top of me. Sarah moved on top of me. She squatted over me. I was supporting her. She reached around behind her grabbing my cock to line it up. Sarah lowered onto me. She pressed down and then I popped in. Sarah lost her balance and her legs went forward as she collapsed onto me. Sarah wrenched in pain as my cock went fully into her ass. She twisted and it bent me back further causing major discomfort for me. She was able to get on her knees. She pushed me out and rolled over. Sarah was visibly upset it was much more painful than expected.

I wasn't sure what to do. I really wanted to have anal sex. I figured if I went down on her it would make her feel better. Sarah stopped me. She put both hands on my face and asked if we could just fuck like normal people. She opened her legs up,I got between and slid myself into her. We went very slowly kissing each other. After our second time, we showered off and had sex one more time before she left.

Sarah and I eventually figured out to do anal...with less pain for her over the next semester. Sarah came clean and told her partner about me. It wasn't well received and they separated. Sarah continued to only date women and just have sex with me until I graduated and moved away. A few years later Sarah moved away to be with her new girlfriend she met online. To this day, Sarah was the only one I ever had anal sex with.