“What’s wrong?” She noticed the tone of my voice and jumped up. I was frozen. Words escaped me. My jaw was stuck open and my eyes screamed with disbelief.
It took Casey a few seconds to realize what was going on. “O my God. I thought you knew. I am so sorry. I thought you knew.” She was scurrying now and looking for the shirt she had dropped earlier. She put on the shirt, grabbed the pants and ran out of the room crying.
I don’t know how long I was waiting and frozen in the position but I eventually came back to. I heard Casey moving around outside in the living room. I heard the door open and shut. I thought about her sitting in the bus station in the cold. I didn’t want that. I put my pants back on and ran after her.
“Casey come back.” I am not sure where she thought she was going. She had no car and it was freezing outside. Her parents lived like 10 miles away. “Come back. I am sorry. Come on. Get in the car. Let’s talk.”
She reluctantly came in when she realized the futility of her plan, or the lack thereof. We were back in the living room now, fully clothed. It was a little past midnight. I made both of us some tea but it was really an excuse to run to the kitchen and think. I had known Casey for 3 years and I had no idea she was trans. I guess there were a few clues but how was I supposed to just guess? Even if I did, was I supposed to ask my secretary if she was born a dude? But I really really had no clue. She was so… feminine. I was confused and angry, mostly at myself and my own cluelessness and stupidity. I felt like an old ignorant fuck who was insensitive to people around him, even the people he loved.
The water heater beeped and I realized I had to face her again. I didn’t know what to do. But there was one thing I knew. I didn’t want her to be upset. That thought echoed in my brain. Her face when she realized what was happening in the bedroom was heartbreaking. I didn’t want to see that again. She was a sweet person. She didn’t deserve that.
I set the tea down in front of her and she nodded to thank me. We sipped our cups awkwardly. The clock ticked. One of us had to break the silence.
“I am sorry, Casey.” I found myself saying.
“No, Teddy. Don’t be sorry. You have nothing to be sorry for. It is all my fault. I thought you knew. I was wrong to assume anything. You have always been loving and kind to me and I mistook your kindness for attraction. I saw what I wanted to see.”
I was chocking over my words a bit. “I don’t think that’s entirely true.”
“What do you mean?”
“What do I mean.. Casey you are incredibly attractive. That hasn’t changed. You are gorgeous girl. It is my fault. I am sure if there were many clues over the past 3 years. I am the one who is closed-minded and ignorant.”
“Don’t say that. I am the one that rushed to conclusions… but are you saying you are attracted to me?” I genuinely didn’t know. Was I? She was still gorgeous. That hadn’t changed. And she was still the girl that I knew and genuinely had feelings for for the last 3 years. “It’s ok, you don’t have to answer that. Can you just bring me to my parents place, please?” I had taken too long to answer.
“Just hold on Casey. I am just thinking…” I exhaled in defeat. “Casey I am 42, almost 43. I have spent a lot of time thinking about myself one way. You are making me doubt that now. Just give me a minute to think.”
She got up from the chair she was sitting on and came and sat next to me on my couch with her body turned towards me. She took my hands in hers. “Teddy, you don’t have to change anything. You are a great man. I don’t want you to change. All what you need to ask yourself is if you still feel the same way about me. Do you still find me attractive? Do you still like me? It’s still me. I am still your Casey. That’s what you need to ask yourself.”
Her words rang in my head. For a girl who was 20 years younger than me she has always been smart and wise. She was right. She hadn’t changed. She is the same girl she has always been. The girl that filled my life when my life was empty. She was the same girl. She also wasn’t any less attractive. If anything I was more attracted to her now after being close with her and seeing how attracted she was to me.
I felt my heart beating in my ears. The tea for some reason had made my throat dry and my hands were sweating in her hands. Or maybe her hands were the ones that were sweaty.
I looked up and looked at her hazel eyes. I tried to find words.. carefully measured words to respond.. not words of consolation.. not words of apology. I air was heavy in my lungs and I felt my body sink deeper into the couch. Our hands still intertwined. I leaned closer and so did she. Gravity brought us together as two objects in space attracted to each other. Gravity.. attraction between two discreet objects. The closer they are, the stronger the attraction, the stronger the bond.
At once my search for words ended.. I had found the words on her lips. We kissed again. But this time was different. This time I had the conviction and she was timid. She was hesitant.
As we kissed I freed my hands from hers and laid them on her waist and pulled her towards me. I felt her shiver. I stood up and grabbed her hands. She looked up at me with eyes that asked, “are you sure?” Somehow, I was sure. I pulled her hands and stood up. I pulled her back into my bedroom.
This time I pulled the shirt up. I pulled the pants down. I took my shirt off and my pants off too. We stood in front of each other in our underwear and stared into each other’s eyes for a second. I had my hands on her waist now and I slowly slid a finger under the lining of her panties. She looked down to see what I was doing. I followed her. Somewhat to my surprise I was hard again. She reached into my underwear and dropped it down. My cock stood erect. Our bodies were close enough that the head of my cock rubber against her panties.
She was still timid now. I could tell by her body language and her flaccid cock. I went to pull her panties down. She stopped me. She held my hand and stopped me. “I don’t always… um.. get… visibly excited.”
“Ok” I didn’t know that was possible. I didn’t know anything. This was new territory. But I wanted to know. I wanted to learn. I was curious. “Let’s go to the bed.”
I planted my lips on hers as we both slowly and clumsily inched back towards the bed. She fell back on the bed first and I fell on top of her. She crawled back a little more and rested her back against the back of the bed. I knelt on the bed and crawled towards her. As we kissed my dick was rubbing against her. It lay on top of hers, separated only by the thin fabric of her pink panties. I could feel it.
I felt I was ready. I wanted her. I leaned over and whispers in her ear. “I am ready. I want to be in you.” Upon hearing that could feel her melt under my touch. She had given in to letting this happen and she wanted it as much as I did. The trepidations she had evaporated.
She slipped her hips down and threw her legs in the air in between my body and hers. When she did this she reached down and instead of taking off the panties she pulled them off to the side revealing her asshole. It was puckered and pink. She spit on her hand and rubbed it on the head of my cock. Then spit again and rubbed it on her asshole. When she was ready she looked at me and I knew.
I grabbed my cock at the base and aimed it at her puckered pink hole. She winked. I had never done this before. I had no idea what to expect. The head of my cock pushed against her now and I was scared to push. There was resistance. “Do you have any lube?”
“No.” I was scared that it wasn’t going to work. She smiled nervously. “I have lotion”.
“Sure” she said. The bottle was in a bottom drawer somewhere. I had to turn over a few things to find it. I quickly squirted some on my hand and lathered my cock. I squirted some on my hand again and lathered her asshole. “Oh”. She flinched “it’s cold”.
“I am sorry”.
“Don’t be” she reached down and with her hand grabbed one of my fingers and maneuvered it. I understood what she wanted to do. I slowly slid my finger inside her. It was tight. Even for my finger. I felt the pressure of her asshole closing around my finger. “A little more lotion.” I squirted more and spread it around and inside. My finger slid all the way in. She grabbed my wrist and pulled it a little bit out. Her legs were still thrown in the air. I could see the outline of her dick inside her thin panties. She was still soft.
“I think I am ready.”
“Me too.” I said. She reached down and grabbed my cock and positioned it at the entrance of her asshole. I squirted some lube on my cock. It was cold. But I didn’t care. I was hitting a block initially. She wouldn’t open for me. But she reached down and grabbed my right arm and pulled me in. I took that as a welcome and pushed harder. After a quick thrust my head slid in. I heard her let out a moan of pain and pleasure. “You ok?” I was genuinely concerned.
She looked me in the eyes and whispered, “You are inside me.” I was. I felt her ass close around my cock. “Go further in” she said. I slowly slid my cock deeper and deeper. Inch by inch it slowly disappeared into her welcoming asshole. “Oh” I froze. “That’s deep” I pulled out. “That’s ok. Don’t pull out. Just go slow”. Once again I slowly pushed in. She moaned again. I thought it was more pleasure than pain this time. When I reached the same depth i began to pull back again, always keeping my head in. I tried again. She wasn’t going to get any looser. I again went very slowly. Watching every inch of my cock disappear inside her. “Teddy” I froze again. “I want you to fuck me now.”
That was the signal for me to pick up speed. Only a little at first but more with every thrust. She remained tight but her moans got louder, only stopping to kiss me as I kissed her. I was picking up speed now. “Fuck Teddy. I have wanted this for so long.” Her words made me pick up speed. I was sweating now and beads of sweat dripped from on my forehead on the pillow behind Casey’s head. Her body bounced with every thrust of my cock into her. With every moan she let out I felt closer to her. Our bodies felt like one. I had to stop. I was getting close.
“What’s wrong?” She whispered.
“You are just stunning. I had to stop. I am getting too close.” I was breathing heavy. I wiped my sweat from my forehead and looked down. The head of my cock still rested inside her asshole. “You are hard”. Her cock had once again bulged in her pink panties. Her head peaked out from under it. She smiled. She was little embarrassed. She reached down with her hand and rubbed it from on top of the panties. I didn’t know what to do. Should I touch it? Should I stroke it for her? Maybe I should suck it. I realized I was staring so I stopped. I looked up to see Casey. She looked perfect. Her hair was spread out on the pillow behind her. Her hazel eyes tracking my moves. Her face, gorgeous, warm and endearing. Her bare chest. Her breasts and nipples. He flat stomach. Everything was perfect.
I positioned my cock and slid inside her again. This time I met less resistance. “Teddy” she said in a sultry seductive voice.
“Yes”
“I want to you to fuck me hard and I want you to blow your load all inside me.” I started to thrust. She screamed “fuck me, Teddy…” I didn’t hesitate. She used one hand to grab my back and pull me closer to her and with the other she rubbed her own cock under her panties. “Don’t stop, Teddy. Please don’t stop.” I liked how she said my name. How she screamed it as I rammed her ass. “Give me your cum, Teddy. I want it.” I was thrusting harder now. Her head was close to hitting my headboard. I felt waves of pleasure slowly rise and wash over me. I let out a moan as I unloaded inside her. “Fill me up, Teddy.” Her voice was a little more frantic now. I thrust a few more times and emptied myself inside her.
After I felt my whole load drip into her asshole. I slowly pulled out. My cock slowly flopped out of her asshole. It stayed a little open and then with a wink it closed. As it closed a drop of my load dripped out. Casey, with her hand, reached down and scooped it up. She then slid her cock out from under her panties on the side. She used my jizz as lube and jerked her cock off. Her cock was skinny and small. Smaller than mine at least. She jerked fervently for a few seconds. I stood there and watched her, now kneeling on the bed next to her with my semi-flaccid cock in between my legs. Another drop of jizz dripped on my thigh. She rubbed her cock and I saw her back arch. She moaned loudly, as loud as she did when I was fucking her. Two small drops of cum spurted out of her cock on her stomach.
Satisfied she dropped her arms down by her side. I, equally satisfied, laid down next to her. She looked at me and smiled, “Teddy, I am really happy right now.”
“Me too.”
“I don’t know about you but I have liked you for a while. I have wanted this for a long time.” I reached my arm around her and took her under my arm and kissed her once. Our naked bodies fit together well and we kept each other warm. We felt serene and satisfied. There would be time to think about what happened and what this was and will be. But in that moment, we were happy to be together and with each other. We slept in each other’s arms. Tomorrow would be a different day.
Source: reddit.com/r/eroticliterature/comments/japt4u/midlife_crisis_part_3_mt