CHAPTER 5
A Son’s Farewell

That summer I spent with John at Martha’s Vineyard was the last time I would be in control of my own life. But at the time, I didn’t know it.

When I returned home, I simply spent one week packing to leave for Chicago where I would be starting college in the fall. It was now late July and I had a lot of things to do before fall term began. As a graduation present, my parents gave me a brand-new car, so I packed, said my farewells and drove off to Chicago.

Just as I was about to leave, I found myself alone with mom in the living room. Dad had gone back upstairs after wishing me luck and mom was staring at me with a guilty look in her face.

“Honey, I’m sorry I neglected you all these years. I know I was very wrapped up in my things and you must’ve been very lonely staying home... alone.”

“It’s okay mom. I really didn’t mind”. I actually meant it. I was thinking that if I had spent more time with her, I would’ve eventually made a move on her or I would’ve revealed my little secret to her and tragedy would ensue. For now, I had to keep my secrets to myself and enjoy her presence these last few moments. She looked very hot. She was wearing tight black pants that accentuated her figure and a pink, Halston, silk top.

“I should’ve given up all those stupid activities that kept me from spending more time with you. I feel like I don’t know you anymore. Your friends, your interests, your girlfriends... if you even had any of them.”

As she mentioned the word “girlfriends” I looked away. I was never interested in any girl... except for her. And I didn’t want her to know that.

“I’m sorry, Ashton. I promise I’ll make it up to you...” She walked over and hugged me. It was a magic moment. She was vulnerable and opening up to me and I was more attracted to her than ever before. As I felt her breasts push against my chest and the softness of the silk against my hands, I got a huge erection. It was beyond my control. Every fiber in my body wanted to kiss her and fuck her brains out on the couch. I obviously had to restrain myself, but despite every thought of restraint, I put my arms around her and held her tight. As I pressed her against me, my dick pushed against her crotch and my hands began to make their way down her back to her ass. I reached her butts and I began to cup her ass as I slowly turned my lips and kissed her softly behind the ear.

To my huge surprise, she let out a grunt of pleasure. She closed her eyes and slowly began to turn her head. I closed my eyes and made my way to her face. I wasn’t thinking anymore. I was letting my inner feelings take over. So I ran my lips over her face until I found her mouth. By now, she was letting herself enjoy the moment. Our lips met and we fused in a passionate, deep, long kiss. Our tongues would play with each other in loving embrace. My hand made its way and cupped her breast. She sighed in pleasure and my dick got harder so I pushed my pelvis against her, dry-humping her pussy. But suddenly, she freaked out, pulled back and stared at me. I was helpless. I couldn’t hide my feelings anymore. I guess she must’ve seen right through me, because suddenly she blushed and ran upstairs without saying another word.

I felt dumbstruck. I couldn’t move. Everything felt weird. Without saying a single word, and with a simple gesture of love and lust, I had revealed my true feelings for her. I was totally embarrassed and the situation had turned awkward. Should I go upstairs and talk about it? Or should I simply go, let things cool down, then talk to her on the phone? I chose the latter, and simply walked out the door.

Little did I know that it would be the last time my mom would see me the way I was. Little did I know that I was about to die… and be reborn.

On the car ride I kept going over the incident in my head. When I felt her firm, supple breasts against my flat chest I pulled her in and at that moment she didn’t pull away. Then I moved my hands down her back and cupped her ass, and she didn’t move away, either! In fact, now that I was thinking about it, she was responding to my touch. It wasn’t until I pushed my dick into her pussy that she backed away. And then she blushed! SHE BLUSHED! That meant that she ENJOYED IT! She wanted more. And she knew that I wanted more.

I wanted to turn the car around and go back home, but I knew that was impossible. I mean, what about dad? How would I explain it to him? I just had to keep driving to college.

A day later I arrived in Chicago, and before the week was up, I was already settling into my new apartment. I eagerly called home. The excuse was to give my parents my phone number. But I really wanted to talk to mom. I was hoping she would pick up the phone. Sure enough, Mom answered the phone. Although several days had passed, the situation was still awkward between us.

“Mom, I... I want to explain something.” I said.

“Look, Ashton. There’s no need. Really. I know your dad and I have grown apart over the years and I haven’t had sex in a while, and I may be a little... confused. I don’t know. I don’t know if I sent any signals out to you that you may have mis...understood. I certainly didn’t mean to. But I... I... felt... you...” She sighed, “Oh, my God. I... felt your... against me. It felt so hard... And the worse thing is that I have missed it so much that I... But you’re my son and it’s so wrong...” Suddenly she started crying over the phone. “But I don’t want to ever discuss that again. Understand? Never. It was a brief moment. It was wrong. It’s sick. It’s so wrong that I can’t even begin to tell you why it’s so wrong on so many levels. So let’s leave it at that. Maybe it’s best that you moved out to college now.”

“Mom, please. I can explain. Really.” I pleaded with her.

“No. Some things are better left unsaid. I said I never want to talk about this again. You’re my son and I love you. But not like that. I hope you respect that. I’ll see you for Thanksgiving... maybe. Good bye, SON.” Then she hung up and the line went dead.

I hung up the phone. I put my face in my hands. I felt awful. It was like I had been caught crossdressing. Thank God that part of me was still safe. I knew that after revealing my feelings for her, mom would distance herself from me. But if she knew I was a crossdresser, I’d lose her for good. To distract myself from these thoughts I began unpacking.

As you might’ve guessed, I had stolen a few dresses from John’s house, and I still had my mom’s old dresses. I couldn’t wait to wear them all the time in the privacy of my own apartment. Nevertheless, as I was still settling in, and had various people coming in and out of my apartment (such as the cable guy, the phone co., etc.) I exercised some level of self control before indulging in my private habits.

That summer was particularly hot, and as much as I wanted to shave my body, I chose to wait for a couple of months, otherwise, I wouldn’t be able to wear Bermuda shorts or swimsuits without getting weird stares or having to provide needless explanations to strangers.

By the beginning of my second week, my apartment was beginning to look half-way decent. My special clothes had been hidden behind a wood panel in my closet and most of my regular clothes had been put away.

The cardboard boxes had been thrown away and aside from a few books, magazines and dishes, I was finally settling down into my new college life. I was two weeks away from the first day of class, and mostly I had been going to the university to register, and get most of the info I would need for the next few years.

The saturday prior to my first day in college, I was so tired from the move, that I ordered a pizza. I sat down in front of my TV. ready and started eating my mushroom and pepperoni with double cheese. I was half-way through my third slice, when the phone rang.

“Hello?”

“Hi, buddy! How are you doing?”, the voice came from the other end.

“John?”, I asked in disbelief.

“Hey! You still remember me! I’m touched!”, he said jokingly.

“Hi. It’s great to hear from you. Are you looking for my dad?”

“No. I know your dad is back East. I just saw him a couple of days ago. He’s the one who gave me your number. Actually, I’m in town, and I was wondering if you’d like to join me for dinner”.

“Yeah, sure. That’d be great”.

“Terrific! I’ll pick you up in 20 minutes.”.

“Okay”. I changed my tee shirt and put on a pair of jeans, then put the rest of the pizza away and waited for John. I was really glad to know he was coming over. I had been alone for so long, that I welcomed the company of a good friend.

A few minutes later John came by and we went to a nice restaurant in downtown Chicago. During dinner, John explained to me that he was in town for a quick business trip, but that he had found out where I was and he thought it would be a good idea to spend the weekend together. Naturally, I agreed, thinking it would be a great way to spend some time before I started classes.

After dinner, John invited me over to his fancy home for a drink, and once again, I had no reason to refuse. In fact, it would be a welcome change of scenery.

His Chicago estate was huge. In fact it had a small bungalow on end of the property. The house had a swimming pool, tennis courts and huge gardens that were perfectly groomed.

By the end of the evening, after we had shared a great time together, he suggested that I stay the night in the bungalow. I was so tired that I agreed. He walked me over and quickly showed me where everything was, then he excused himself and I crashed on the bed. I was so tired, that I didn’t even get under the covers, I simply drifted into a heavy, restful sleep.