It was late August, and my daughter Morgan would be leaving for college soon. As we were preparing for that, my mind kept going back to her best friend Kelli. When they graduated high school, Kelli approached me and asked if I could take her virginity; she wanted her first time to be with an experienced man. After resisting her proposal, I finally gave in and said we could do it on the condition it has to be a one-time only hookup.
We did have sex, and afterward, she lamented that this was to be our only time together. I suggested that maybe we could have a "send-off" tryst before she leaves for college. I immediately regretted saying that, because what happens if she ends up having deep feelings for me? In that regard, I was more concerned about how that could affect the relationship with my daughter; if she found out her best friend and me were having a secret affair, what are the repercussions?
Since my wife died nine years ago, I've had only two other relationships; one ended after she got tired of me, and the other ended when it was clear she had no interest in being a mother figure for Morgan. Because Kelli's mom already was a go-to when Morgan couldn't talk to me (i.e. female issues that men know little, if anything, about), I decided not to pursue anyone until after she left for college. I didn't want Morgan to get her hopes up for a great stepmother, only to be let down.
I wanted to call Kelli and tell her we can't do this again, that we agreed on only the one time. Yet, I couldn't bring myself to it. Was it wrong for a 48-year old to deflower an 18-year old? Yes. Even though it was legal and there was consent--SHE was the one who made the first move--that doesn't make it right. But I wanted another hookup almost as much as Kelli did, and decided to go for it.
The week before Morgan left for college, I texted Kelli, asking if she still wanted to get together again. She replied in seconds, with an emphatic "YES"! We decided that it would be the following Saturday, after I dropped off Morgan at college. Kelli's parents were driving her older brother back to school that day too, and because it was a ten-hour drive one way, they were staying at a hotel and return the following afternoon. That meant Kelli and I had a lengthy window when her parents were out of town.
Did I feel sleazy for pursuing Kelli? Yeah. You need to be looking for women from your own generation, for crying out loud. But then I would see Kelli, a tall, pretty brunette with drop-dead legs (my favorite body part on a lady), and those inhibitions quickly disappear. Just do it, and if you still feel guilty, go to church and pray.
The next week, I drove Morgan to school to get her moved into the dormitory. Kelli joined us, and they sat in the back seat together, chatting and giggling about all sorts of topics, like girls do. This was likely the last of many trips where I would be in the driver's seat and Morgan/Kelli were in the back seat, like I was their chauffeur. Kelli was in my rearview mirror's reflection and on one occasion I checked the mirror for other vehicles, only to see her beautiful face giving me a very sultry stare.
When we arrived, I moved Morgan's belongings into the dorm. Morgan and Kelli were too busy talking to help me, but I didn't care. They were best friends since third grade, and now would only see each other on holidays and summer break, so I let them have their space. After the three of us had a late lunch, Kelli and I left, and she was emotional.
"How are you feeling, Kel?"
"I'm going to miss her, Mr Dawson. Morgan I have rarely been apart for longer than a few days ever since we were nine years old, and now we have to go separate ways." Kelli's eyes were welling up.
"You're such a great person, Kelli. I knew that when you first befriended Morgan. You kept visiting her after her mom died, trying to cheer her up. And you DID cheer her up. I honestly don't know how things would have turned out if you weren't around to give her a shoulder to cry on. I can fulfill a lot of roles as her dad, but she needed a friend, a peer, who can relate to her struggles."
Kelli sniffled. "Thanks Mr Dawson. That means a lot to me."
Shortly thereafter, Kelli turned the conversation to our upcoming night together. "Well, Matt--I can call you Matt now, right?"
"Yes, please do. It would be weird to hear you call me 'Mr Dawson' while we are going at it. Know what I mean?"
Kelli laughed. "Yes I do. So...what do you have planned tonight?"
"Well, I think you should spend the night. That gives us lots of time to see how things transpire."
Kelli looked very surprised. "Seriously? I figured we would spend 2-3 hours at most; but the whole night?"
"Sure, Kel, why not?"
Kelli looked at me with her gorgeous green eyes. "Wow, I just didn't think about this...uh, well, yeah! I would love to spend the night with you. I mean if this is our last time together, let's take advantage!"
"Good, Kel. Let's have fun tonight--and tomorrow morning. But this absolutely HAS to be the last time. If you and I engage in a sexual relationship beyond tonight, Morgan will somehow find out about us, and that's going to be a big problem. She's the most important person in my life."
"I promise, Matt. This is the last time. I won't like it, but I understand. Besides, you told me I'll find a great guy at State."
"Yes, I did. And you will."
Kelli leaned over from the front passenger seat and gave me a hug (all the while I'm trying to focus on driving 70 mph down the highway).
I dropped Kelli off at her house so she could pack an overnight bag. When I went home, waiting for her to show up, I was (amazingly) still having second thoughts. Good grief, I told myself. Grow a fucking pair.
I sat on the porch, drinking a beer to try and calm my nerves. At 8 PM, Kelli appeared, walking up the driveway with her overnight bag. Earlier, she was dressed in a t-shirt and jeans, presumably because she would help move Morgan in (she didn't, of course). Now she was in a short flowing dress, hemline well above the knees, showing off her beautiful smooth legs.
I motioned to her to get inside. My neighbors generally keep to themselves, but it would be my dumb luck to have one of them see Kelli and gossip to the whole town that something was going on between us.
Kelli plopped down on the couch. Seeing my beer, she asked (like she did two months earlier) if I could give her one. This time, I didn't rebut her, and got a fresh bottle out of the refrigerator. "Cheers" I said, as we clinked the glass bottles.
I sat beside her, having flashbacks to June, when we sat on that couch and she was nervously awaiting her first sexual experience. Now she was completely chilled out, enjoying my company. Kelli pivoted so that her gorgeous legs were across my lap. As I caressed them, she asked me what we were going to do first.
"Definitely dinner. I've got a small roast in the crock pot."
Kelli and I sat at the kitchen table and ate. I wanted to have her for dessert, and I'm sure she wanted me too, but we settled for ice cream instead.
