My wife Karen works as an economics instructor at a local community college. She enjoys her work for many reasons, one of which being that the environment gives her plenty of eye candy.
A few years into our marriage Karen and I started exploring the swinger lifestyle. We've both always been very open minded and enjoy being able to indulge our fantasies together. We've had some incredible sex and made some great friends in the process.
While Karen has several different "types" of men depending on her mood, she has always had a thing for younger guys. She likes their fit bodies and sexual stamina. As we've aged, Karen has also enjoyed becoming the "older" woman young guys are always attracted to.
At thirty nine years old Karen has made it a point to take care of herself and stay in shape, which of course leads to plenty of male attention. She is 5'9" with long brown hair, amazingly sexy eyes, and a wonderfully toned body. Her breasts and ass are perfectly proportioned and she loves taking her male students by surprise on their first day of classes.
Last night she and I went out for dinner and spent the evening talking about life and reminiscing about some of our greatest sexual experiences. We had a great meal and took the opportunity to get ourselves worked up and horny for an awesome night of sex.
We've played with many people over the years-men and women-but some of our hottest encounters have been with a guy named Mark. Mark was one of Karen's students and it all started when he enrolled in her class. Karen has done her best to not get involved with students or coworkers to avoid any conflicts, but there have indeed been a few instances where it was basically unavoidable. Once Karen finds someone she's really interested in, she gets what she wants...and Mark never stood a chance.
Mark enrolled in community college after high school to get his basic classes knocked out before transferring to a four year university. He of course took an immediate liking to Karen as soon as he began her class.
Mark's parents were apparently very absent from his life and he wasn't used to getting much attention. He was shy and a bit nerdy, but easy to talk to once he got comfortable. He responded to the personal attention Karen gave to his success and began opening up to her more and more. He soon began coming by her office to talk, even when he didn't really need anything.
Eventually it became clear that he had a thing for her. Karen and I talked about it from time to time and initially her interest in Mark was strictly limited to being a positive presence in his life, but as time went on her interests grew past an academic relationship.
I specifically remember an afternoon when Karen and I had taken a week day off to run a bunch of errands together and had to swing by the school to grab something from her office. We ran into Mark on the way out of the building and I noticed what an interest they seemed to take in each other. I also noticed Karen consistently looking down at the bulge in Mark's jeans as they talked. I think she was trying to hide it but to be fair, that bulge was hard to miss. Albeit nerdy, Mark is very well built.
The big problem Mark had in those days was that he had no idea how to interact with women. He was desperately shy (aside from talking with Karen), had never gotten any meaningful female attention, and of course had zero sexual experience.
Mark began confiding in Karen about his shyness and she did the best she could to listen and give him ideas on how to approach/interact with women. His confidence greatly improved with Karen's help, but it never got him very far. During the entire year he attended community college he only went on a few dates, and certainly never had any sexual contact. I remember Karen telling me about it and the fact that she seemed genuinely disappointed.
Mark finished his first year of classes and was set to go to university in the fall. He had plans to simply enjoy his summer off before returning to school. By that point even though classes had ended he still kept in touch with Karen. Phone calls led to lunches, which led to him visiting our house.
A few weeks after classes ended he was at our house complaining about another failed attempt at getting laid. His buddies had set him up with a girl that was known to be a bit of a slut. They went on a date the prior evening, which actually went well given Mark's shyness, and eventually got to the point where the girl was ready to get physical.
Mark said he completely froze up at that point. He explained that not only did he have no clue how to navigate a woman's body, he had never even tried to put on a condom.
He left that afternoon with Karen and I a bit shocked at how completely clueless Mark was when it came to anything remotely sexual-even for a guy his age.
A few nights later he was back at our house freaking out because he had managed to get another date with this girl. He was complaining that he didn't know how to make out and probably wouldn't make it past trying to put on a condom.
Karen and I sat there listening to this and she would periodically glance over at me with this look...and I knew what that look meant. I had known for a while that she was fighting herself on this one, but it looked like she was ready to give in.
Finally Karen said "Why don't I help you with a little practice." She went over and sat next to him on the couch, putting her hand on his leg. Mark looked at me like he was about to die and I said "Go for it. She'll get you ready for that date."
Karen leaned in and touched her lips to his and I could see his dick starting to grow immediately. They started kissing and I watched as Karen gave him pointers. A few minutes into it she started telling him how to move his tongue inside her mouth, at which point my cock started getting hard too.
After kissing for a few minutes Mark's cock looked like it was going to rip through the gym shorts he had on. Karen kept looking down at it and I knew she was dying to get those shorts off.
"Do you feel better about kissing?" she asked. "Yes" Mark whispered.
"Good. Now we need to make sure you know how to put that condom on" she said.
"Pull your shorts down." Mark did so, revealing his massive cock.
"Wow" Karen muttered, her eyes locked on his huge dick, desperately trying not to get ahead of herself.
"You definitely won't get any complaints about that thing" she said with a smile.
Mark pulled out a condom and Karen began giving him pointers on how to put it on comfortably.
Once the condom was on Karen grabbed his shaft and squeezed a little bit. "Does it feel comfortable?" she asked. "You want to make sure it doesn't come off while you're fucking her" she explained. Mark just nodded that he understood. He looked like he was about to cum on himself and I couldn't help but laugh.
