My Second Affair: Curvy Emily

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My second affair came three years after my first. Her name was Emily and, like Sarah, was a student of mine at a small, Midwestern, liberal-arts college. I am anxious to recount my stories accurately as a record of this important but secret side of my life. I need to tell someone, so thank you for reading.

I ended my relationship with Sarah abruptly and painfully. As I stated in that story, I chose the woman I married over the woman loved. I quickly fell into depression. I hated my life. I cried a lot. I wallowed in self-pity. I wasn’t suicidal but once on the way into work some asshole was texting and crossed right into my lane. I never swerved but instead just relaxed my grip on the wheel and accepted my fate. He jerked the wheel at the last minute and missed my truck by inches.

Three years passed and I was still miserable in my personal life but it hid that fact from everyone. Anyone that knew me would have told you how happy I was, how perfect my life was. But on the inside my guts where churning. I had promised myself I would never have another affair. But then Emily came along. She was a transfer student from another college, where she had pursued an unrelated major. At 27, she was older than the average student and almost 13 years my junior. In the fall, she was just another face in the large introductory class I teach but each semester, I teach another class that includes a weekend camping experience and is required for all students in the Environmental Studies degree. Emily took that class in the spring semester.

April can be a challenging month to camp where I live, but I remember this particular weekend was bone dry with a perfect amount of chill in the air. That was an added blessing since I had been unable to find a student aide to assist with the class. Friday evening ended with us all sitting around a campfire, formally introducing ourselves and sharing stories. As students excused themselves for their tents, the circle got smaller until there were only a few of us left around the burning embers. With a big sigh, Emily stood up and said, “Time for me to call it a night. See you all in the morning. Good night, Jay.”

As she walked behind me, she laid her hand on my back and slid it across from one shoulder to the other. I jumped. I was not expecting to be touched and by the time I turned my head, the contact was over and she was walking away, to her tent. Was that an invitation? I concluded it was. I reevaluated Emily as I watched her disappear into the darkness.

Emily was 5′ 5″ tall and best described as “curvy”. I am not trying to be insulting here, but I do want to report this honestly. She wasn’t thin however I would never describe her as fat. As I came to learn, she was a runner, so her frame was built on a solid chassis. Her black hair was wavy and didn’t reach her wide shoulders. Those shoulders framed some very large breasts (Later she told me the boys in middle school teased her and called her “Dee Dee”). Her middle tapered and her waist flared out, but not as wide as her shoulders. Her short legs were strong. She hiked long and hard, just like she fucked. I can still imagine those ankles locked around me as she drew me into her sloppy wet pussy… But I am getting ahead of myself.

The physical feature that attracted me the most was her face. She had intelligent eyes that sparkled when she talked. Her smile and laugh were contagious and devilish. She had a biting sense of humor that betrayed her New York City upbringing. I sat at that campfire for an hour after the last student left, watching the coals burn to nothing and thought about her “offer”. What if I misread that and she was just being friendly? What excuse could I come up with for waking her up? And most importantly, was I ready to begin another affair? I decided against action and reluctantly made my way to my tent to jerk off and get some sleep.

The schedule for the next day was a simple one. After breakfast, we were to hike up to the overlook and complete a journaling activity before heading back to camp. Then it was free time until dinner and a quick service project before roasted marshmallows around the fire.

Emily gave no further signals that I caught and by the top of the mountain, I was convinced I had misread the situation. But by then it was too late. I had already imagined all the things I would like to do to her. I hiked with a half hard cock and a slight buzz in my head. By the end of the hike, we were all sweating but smiling. It was a challenging hike and we were rightfully proud of ourselves. I grabbed a quick nap before dinner and then got a cook fire going. By this time in the trip, I am usually a hot dirty mess. I enjoy the chores that go along with camping and split my share of the firewood. And at 40, I was in good physical shape. No one would accuse me of being a professional athlete or body builder but I do have muscular arms and a chest to match. Couple that with my hiking legs, and I can hold my own in the gym or on the marmaris escort track.

After dinner, our service project was to clear an area of dead limbs and burn the pile. Perhaps not the most environmentally friendly project, but the students were looking forward to the resulting bonfire and it was what the managing agency wanted. Everyone pitched in to create the pile but after a half hour of burning, most of the students had wandered off to the smaller campfire or their tents. I was left with four students, all female. None of them made a move to tend the fire, so I made it my responsibility. I shifted logs and added more branches. In the fading light, nothing was visible outside of our lit area. I sweat as I moved the wood and my face and arms became smudged black with soot.

I did not know it at the time, but at least three of the four women that sat there around that fire were only there to watch me work. How do I know that? They told me, eventually. Emily was there, of course and so were the two students that were to later become my third and fourth affairs (stories for another day). Holly was the only one who I did not end up in a relationship with and as I recall, did most of the talking.

At the time, I was still trying to determine if Emily was interested in me or not. As I worked, I rolled one of the logs closer to the center of the fire and in doing so, sent ash into the air. I was too close and unable to close my eyes in time. God how that stings! Eyes watering, I made my way over to the girls. Holly was telling another story that everyone was politely listening to. I picked up my water bottle and sat down next to Emily.

“Will you flush the soot out of my eyes?” I asked.

“Oh, yeah. Sure, Jay”, she replied. I laid on my back next to her as she sat cross legged, unscrewing the cap to my water bottle. I held my eyes open, one at a time, as she poured the water over them.

Romantic? Well, I thought so. I certainly caused my cock to stir. With one of her hands on the water bottle, that left her other to cradle my face gently. There is something nurturing about rendering first aid to another that I find attractive and it was not lost on me that the roles were now reversed from my first affair with Sarah.

Emily held my face with her hand under my chin and her arm sweeping up the left side as she sat looking upside down at me. Soon, my eyes were clear and I wiped the water away but Emily did not let go. I laid there for what seemed like minutes but must have only been a few seconds enjoying the feel of her against me and basked in her smile. Abruptly, I sat up and thanked her and left the fire to its own devices. We all sat long into the night watching the wood burn down. I stayed sitting next to Emily on the ground, sporting some wood of my own.

Perhaps I flirted a bit with her in the hallways for the last few weeks of the semester, I honestly don’t recall. I must have. But that summer we went our separate ways and I didn’t see her again until the start of the fall semester. I asked her if she would like to be the student-assistant for me that fall in the aforementioned camping classes. She agreed. The program had seen a large growth in enrollment and I was now teaching three sections of that class each semester.

Our first trip was only a few weekends away and when the date of departure finally arrived, I was still unsure what I was going to do. That first night, I did nothing. Well, I did masturbate to the thought of Emily, but I mean I made no move. It was the second night that I found my nerve.

We had finished dinner and our service project. The project this weekend was a simple one: stack the firewood that had already been dumped and split near the lean-to. We made a game of it and finished pretty quickly. I managed to flirt a little with Emily, grabbing her bicep and telling her it was as hard as the firewood. She laughed heartily at my joke. The sun was setting as we finished and all the students headed to the campfire for a much needed break.

I suggested to Emily that we take a walk around the camping area. She agreed. I led her far off to a mossy spot overlooking the distant campfire. We sat down and talked for a while. Then I stretched out on my back and invited her to feel the soft mat of vegetation for herself. She laid down next to me, both of us staring at the stars peeking through the tree tops. My heart pounded. Surely she could hear it, I thought.

After a few minutes I rolled onto my side towards her. “Can I tell you something?” I whispered.

“Of course”, she said without moving.

“I think you are absolutely beautiful”, I stammered. There. I said it.

Her response back was a laugh. A nervous laugh perhaps, “Um, thank you.”

I was laying on my left side, propped up on one arm and unsure of how to proceed. I could hear her breathing heavily now and I figured that since she hadn’t run, it was a good sign.

“Why did you say that?” she asked.

“Why do I think you are marmaris escort bayan beautiful or why did I tell you I think you are beautiful?” I inquired.


“Well, the more I have gotten to know you the more I am attracted to you. I love your attitude. You are curious and adventurous and smart. I find all of that so attractive. Your eyes sparkle when you talk. Your cheeks bunch up when you smile. And I cannot get your soft hands out of my mind.”

As I said these things, I let my right hand gently fall on her right arm. She did not protest. I bent close to her and waited with my lips close to hers. It was maddening. I wanted to take her in my arms and feel her warmth but instead I stopped there, so close to her full lips.

“We can’t.” Emily paused before speaking again into the darkness. “What if someone sees?”

“Look at them all down at the campfire”, I answered. At that she rolled to her left side and I was now spooning her from behind. “No one can see us.”

“Jay, you’re married”, she stated with finality.

“Then let me just tell you a story”, I replied. It was my intention to tell her all about Sarah. To let he know I had done this once before with another student, one that was the same age as Emily. But I didn’t get all of that out. I couched the truth by referring to Sarah as “a girlfriend” and proceeded to whisper the story of how Sarah and I fucked for the last time in a shower house (I recounted this entire episode in a previous story). I whispered the details of how I made Sarah cum with my fingers and how she agreed to slide one of her fingers into my ass as I stood facing the wall of the shower stall. I told Emily in graphic detail how much that thrilled me and, when I couldn’t take Sarah’s finger fucking any longer, I spun her around and buried my rock hard cock into her until I sprayed a huge load of cum on her back.

There are many reasons why I told Emily that story. It was the end of one affair and I was asking her to start another. It also showed her I was willing to push boundaries. If she was turned off, well then I wasn’t going to get what I wanted out of this affair anyway and it would be better to find out now. Finally, to me, it was a secret. One that wasn’t easy to divulge and certainly one I didn’t want anyone to know about, even without the added detail of this being an affair. My confession felt like an honest start with Emily, despite not admitting to the adultery. It was my largest admission to anyone and felt like a weight was lifted.

When I finished, I had a hand resting on her hip and a hard cock nestled against her ass. She was quiet for a moment before speaking. “That was incredibly hot. Oh, my. Wow”, Emily stammered.

I leaned into her a little and said boldly, “I want to do things like that with you.”

She exhaled sharply. I could tell she was torn. But in the end she only said four words. “But you are married.”

“Ok”, I responded. I wasn’t going to push her. We laid together for a while chatting about what we needed to do the next day in order to break down camp. I offered to walk her to her tent and promised to be a gentleman. She agreed, and I kept my word.

Sundays on these camping trips are always interesting. Some students are early risers and cannot wait to return home while others are more relaxed and want to take their time getting organized. I generally split the difference and therefore make no one happy. Emily was a huge help and together we got everyone together for our last group activity. I did not mention a word of the previous night to Emily but I couldn’t help notice the big beaming smiles she was giving me along with the lingering touches as she passed me.

We arrived back at the college and the students unpacked and sorted the group gear. They were quick and efficient. Emily and I sat close together on a bench and watched the last students heading off to their dorms. I thanked her again for a great weekend and with an apologetic grin, asked her if she was still willing to work with me for the next two trips.

“Of course, Jay. I love spending time with you”, she replied.

“Great. I am glad I didn’t scare you off with my offer”, I answered.

I stuck my hand out as a friendly good-bye handshake, but she laughed and hugged me instead. We both smelled like sweat and campfire smoke but I took a deep breath anyway as I pressed her fully against me. God, she was so soft and round and full. I held her longer than necessary, memorizing the feeling of her against me.

I finally let go and we smiled at each other. We stammered some good-byes and I headed to my office as Emily turned towards her dorm. I wanted to make sure I had everything organized for my Monday lecture as I knew I would be arriving to work tired the next day. As is typical for a Sunday, the other faculty offices in my wing were all dark and empty. I unlocked my door and closed it behind me. No sense risking an interruption from a chatty student or colleague when there escort marmaris was work to be done.

I had just settled in at my desk when I heard a light knocking on my door. I ignored it. Then I heard a small voice inquire, “Jay, you in there?”

It was Emily. I shot out of my chair and threw the door open. I had just left her moments ago but she looked completely different to me now. The sunlight was pouring through the hall window, backlighting her figure.

At first she wouldn’t look me in the eyes but when she lifted her head, I saw a determined look on her face. She stepped into my office and put her hands on my waist. I closed the door behind her and we both heard the loud metallic snap as it locked. I was now holding her waist and bent my head down so my lips were pressed against the top of her head. As she slowly looked up, I kept my head steady so that my lips moved from her hair to her forehead, then down her nose and finally to her waiting mouth.

A first kiss is different than every other. It is not always the best kiss, but each first kiss is memorable in its own right. This one was pure electricity as we allowed ourselves to give in to our desire for each other. My hands were now on her back, crushing her soft tits against my hard chest. She was breathing hard now and I could feel her hands running up and down the muscles of my arms.

I moved my hands from her back to her front and lost them in Emily’s massive tits. These were the biggest breasts I had ever felt and I alternated between trying to squeeze them both with using both hands on a single one. Emily moaned in delight. Her hands were wrapped around me and fell to my ass, as she pressed my middle against her. I slid my right hand down to her crotch and rubbed her pussy through her jeans.

“Oh, Jay. You feel so good”, she breathed as I continued to rub her. The faster I ran my hand over her jeans the more ragged her breath became. I used my left hand to grab the back of her hair and pulled. With her face pointing straight up now, I licked her throat. She moaned and trembled. I quickened the pace on her covered pussy and felt her begin to tremble.

I stopped licking her long enough to whisper, “Cum for me.” I then opened my mouth and raked my teeth over her jaw, finally coming to rest on her chin and gave it a light but firm bite. She exploded. Her legs shook in orgasm as her arms went limp. I held her in place with my right hand now squeezing her damp jeans as aftershocks rippled through her and my left hand still entangled in her hair.

My own jeans were straining as my fully erect cock pushed against them. I spun Emily around and bent her over my desk. She supported herself on her hands and pushed her ass against my grinding hips. I reached under her and grabbed one massive globe in each of my hands as I dry humped her ass. We were both imagining that cock buried in her pussy and I was close to cumming.

I slid my clothed prick against her ass faster and faster. Emily grunted her approval and that was all I needed. I squeezed her tits hard as I drew myself against her ass, trying to will my cock through our clothing and into her wet pussy. I came hard. This may have been the sexiest thing I had ever done fully clothed.

When I managed to catch my breath, I turned Emily around and held her close. We didn’t speak for some time and when we did, it was awkward but not apologetic. I kissed her lightly as she started to leave. We agreed to meet the next day to talk.

The next day came and went without either of us being able to meet. She did send a quick email saying everything was all right but she had forgotten about an assignment that was due and she had been stuck in the library all day. I sent her a reply asking her what she was doing Wednesday morning. A rare bird had shown up at a nearby lake and I was going to try to find it.

“Sounds like fun!” she emailed back, and we arranged to meet at a carpool lot an hour from campus at 8am Wednesday.

Wednesday arrived and I was so anxious to see her, I arrived a half hour early to the meeting spot. I saw that Emily was already there, waiting in her car. She smiled as she recognized my pickup truck and practically ran to it to get in the passenger side.

“Good morning!” I said as a big smile split my face. I reached out a hand and held hers as she settled into her seat.

“Good morning to you too!” she responded. Her smile was as big as mine and we both just looked at each other for a moment, holding hands.

“Well,” I began, “we could go looking for that bird ooooorrrrr we could go over to that motel over there and continue what we started on Sunday.”

Emily stopped smiling and dropped her mouth open in surprise. I was taken aback at her surprise and wondered what had been going through her mind these past three days. Because all I had been thinking about was how I was going to get her naked.

“I…I…I wasn’t even thinking of that. I thought we were going birding.”

“We can,” I assured her. “I would be perfectly happy to spend a morning exploring that park with you looking for this bird. But I also would enjoy being alone in a room with you and seeing what you look like with less clothing.”

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