As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the condom leaving it in my tight ass. I’m finding it to be an after sex turn-on. I sat on the toilet and peed. There was a slight pain in my penis when first peeing. According to what I read on the internet, men and women should pee shortly after sex. The ever so slight pain was more than worth the feeling of falling asleep in Bob’s arms in a pool of cum.
I stood up and looked into the mirror. The hair clips were pulling out and my lip stick was a mess. I removed the clips, brushed my hair back, and put it in a high ponytail that swayed when I moved my head around. I got some cold cream from my make-up bag to remove everything from my face. After rinsing my face clean I applied a light coat of make-up with just a little eye shadow. I took off my sheer nightie, bra, and cum filled panties replacing them with a fuller bra, thong, and night shirt.
I went into the kitchen to see if Bob had anything for breakfast realizing I really hadn’t eaten anything of substance since lunch yesterday. After a few minutes of familiarizing myself with his kitchen I started cooking some bacon while I got out eggs, orange juice, and bread for toast. As I started turning the bacon I felt a pair of hands running up my legs to my near bare ass followed by little kisses on my neck. “I’m in love with this ass” Bob whispered into my ear. “Oh yea, and everything connected to it.”
When I finished making breakfast we sat down at the table and ate. “Joann, you know I’m not gay,” he declared as he washed his last bite down with a gulp of orange juice.
I replied, “Neither am I.”
With a confused look he questioned “How can you say that?”
“How can you?” I shot back. “Let’s hear your definition of gay first, then your explanation of why you’re not. Then I’ll give you mine.”
“Gays are men that like men. They like to give head and receive head. They like giving and receiving anal sex. I only like to give,” Bob retorted.
“Bob, I’m a woman trapped in a man’s body. When did you see me get a blow job or fuck a man up the ass? I’m no more gay than you are. In fact, I’m probably less confused than you at this moment.” This was so true I thought to myself. It was the first time I realized who I was and it felt good.
Bob stood up, walked around the table, and gave me a big hug. “I’m sorry, you’re right. I’m so awkward with women and so comfortable with you. I just don’t know where this relationship will lead us.” He was in tears.
“This is a growing experience for both of us,” I explained. “In June we will both be finishing school and going our own way. I think you’ll be prepared to chase girls with much better success by then.” We sat and talked for a while. Bob confessed that he never had intercourse with a woman. Given his expert moves on me, I told him I would have never suspected. I could see the relief on his face as we opened up some of our problems to each other. “Let’s enjoy this ride,” I said with a genuine smile. He responded with a long deep kiss that acknowledged our mutual feelings.
“Would you like to go out for a while?” suggested Bob. “Maybe a ride to the park to see if the water falls are frozen, an early dinner, a few drinks.”
“Sounds like fun. I need to take a shower and get dressed.”
“There are towels in the bathroom closet. I’ll take a shower when you’re done. Take your time.” I couldn’t help feel that Bob was hoping I would invite him to shower with me, but I wouldn’t be comfortable with all of my clothes off in front of any man. I thought of my breast forms as I went into the bathroom. They had been on since yesterday. However, they were still firmly attached. I went ahead and showered with them still on. They survived the shower so I decided to leave them on in spite of the instructions to remove daily and not to sleep with them.
After my shower I put on lotion, deodorant, and perfume. I looked through my bag and found the sexy girdle brief. It completely pulled my little dick and balls tight between my legs. I put on a full coverage bra along with a tight long sleeve wool blouse. I put the pantyhose from last night on to keep me warm. This was a good idea since the combination of the girdle and control top panty hose made my tight fitting jeans look like I had a camel toe between my legs. There was no sign of any bulge.
I applied new make-up, eye shadow, and lipstick, then blew dry my hair pulling it back into a cute ponytail. I was getting pretty good at this by myself. Sis did a great job of showing me how to do it. I put on the pink sneakers which made me look and feel quite feminine. After cleaning up the bathroom and my dirty clothes I told Bob, “You can have the bathroom now, I’m done.”
As Bob showered, I cleaned up the kitchen from our breakfast so we could leave when he was done. Although I thoroughly enjoyed the weekend so far, I was ready to get outside. When Bob came back out he commented on how good I look, no matter what I’m wearing. He hugged me with his hands around my waist, and then rubbed my ass as I wrapped my arms around his neck. I pulled my tits tight against his chest as we kissed for several minutes. I think he was showing me that we were still lovers after our morning discussion.
We spent the afternoon going to the frozen park, followed by an early dinner and drinks in a quaint dimly lit restaurant. Several times I caught glimpses of men looking at me throughout the day. I also noticed Bob smiling when he saw them. I felt pretty hot and I was getting turned on.
We got back to the apartment around 8:00. I suggested we slip into something more comfortable, open a bottle of wine, and listen to some music. I changed into the last piece of lingerie packed in my bag as Bob put on a loose pair of pajamas. We sat on the couch for a while sipping wine, kissing, and cuddling. I was lying with my head on Bob’s lap as he stroked my hair. It was so soothing and relaxing. I turned on my stomach as he rubbed my back. My face was in his crotch so it didn’t take long before he started getting aroused.
I began to kiss his dick through his pajamas. As it grew I pulled it through the opening on the front. I licked the tip causing it to ooze some precum. Then I opened my mouth taking in his shaft until it reached my throat. This time I knew how to handle it. I quietly said ‘ahhh’ like when the doctor gives an examination. This opened my passage way to receive the head of his dick. Now all I had to do was force it into my throat while I held my breath. I repeated this process several times deep throating him like a pro. When I withdrew, the tip of his dick was full of precum. I licked the thick sweet tasting clear syrup from it before pushing my mouth back over his shaft with my tongue rubbing against his now thick vein.
Once, again, I forced the tip of his dick into my throat. His hands were now holding my head. He pushed my head up and down in five or ten second bursts so I could deep throat him without gagging. After a few minutes I would pull up so I could lick his precum before going back down. His dick was getting a thorough coat of my slobber from the repeated visits to my throat. It was getting easier each time and it was turning me on. I was holding his dick in my throat longer each time. I started using my right hand to cup his balls and wagging my tongue on his vein.
I could feel his grip on my head increasing. He was starting to move his pelvis up and down. I knew he was getting close. I increased the time his cock head was in my throat. His balls were beginning to tighten up as it felt like there was a heart beating in them. He pushed my head down and his pelvis up forcing his dick into my throat as he let out a gasp. I could feel his vein pumping come, but I could not feel or taste any come in my mouth. He was pumping it directly into my throat. Although I knew I was giving him great pleasure, I missed the taste and feel of his come. He was almost convulsing now and I was beginning to gag as I had to push his dick from my throat. However, I kept it in my mouth and sucked it in time to get the last shot of his come where I could taste it a little.
As before, I held still with my lips on his dick as he recoiled a few times before beginning to soften. We both held that position for several minutes before I slowly pulled my mouth off, with my lips sealed, to keep any of his come from escaping my hungry mouth. I really love sucking his cock.
After a few minutes I stood up, took his hand, and walked him to the bedroom. I pulled off his pajamas as we both lay on the bed under the covers to keep warm. Bob spooned me while softly stroking my hair. We both dozed off for a few hours.
When I woke up it was around 1:00 am on the clock on the end table. Bob’s arm was lying across me with his hand on my right breast. I pushed my ass back into his crotch which started to arouse him from his sleep. I turned toward him and pulled my self against him with my tits tightly against his bare chest. My left arm was around his waist and his right arm was across my back with his hand on my shoulder. Our lips met, we kissed, and pushed our tongues back and forth in each others mouth. I could feel his stiff shaft against my pelvis. He was starting to gyrate his body so his dick could tightly rub my body.
I started to push away a little so I could get my hand between us and hold his dick. Then I began to softly jerk him off. I moved my lips from his and began to work my way down his body. When my mouth finally reached his swelling shaft I wasted no time forcing it into my throat. I moved it in and out of my throat four or five times before moving up to the head of his dick to lick the precum. Then I went back down his shaft and into my throat for several long gulps causing a little gagging that caused me to slobber all over his dick. It was starting to get slippery from this repeated cycle.
I sat up and straddled him cowgirl style. Then I reached behind my ass and lined him up with my hungry hole. As I started to ease down on his shaft he said, “Aren’t you forgetting something?”
I replied, “Were you honest with me this morning when you said you never had intercourse?”
His answer was, “Of course I was.”
“We should be safe then,” I said as I resumed lowering myself forcing his dick into my ass. It was different without the condom. I could feel the skin of his head compressing into my anal ring, then expanding back as it passed through inside. There was more friction from his slightly drier skin and rougher texture than the streamlined slippery coated condom. The increased friction generated more heat in my ass. There was more resistance which pushed my sphincter inward elevating my sensitivity. This added a new dimension to anal penetration.
When my cheeks finally rested on Bob’s thighs, I leaned back a little to get it in a little deeper. I sat there a few moments before bucking my hips slowly to feel his dick rubbing my insides. As I started to lift myself up, I could feel his shaft stretch slightly as it clung to my colon without the excess lubrication. Then I could feel his entire length on my inside walls as it resisted sliding out everywhere it contacted. Pulling out was almost as pleasurable as pushing in. In fact, any movement brought pleasure, not only to me, but apparently to Bob, also, as he began to moan.
The added resistance pulling out triggered my muscles to tighten increasing the intensity. Before long, we were both moaning. As I could feel the head of his dick reach my sphincter, I stopped momentarily before sitting back down driving his pole deep into my ass. This time when I bottomed out I started squeezing my ass muscles while fully penetrated. This drove us both crazy. Bob started bucking as his hands squeezed my tits. I thought to my self, it was a good thing we started off the night with a blow job to prolong our fucking. I sat still a few minutes to keep Bob from erupting too soon. Then I started to slowly move up and down. The upward movement kept triggering my muscles to tighten. I knew we weren’t going to last much longer.
I managed to move up and down a few more times before I could feel Bob tense up and start to declare, “Here it comes!” as he pushed his pelvis upward while holding his hands on my shoulders pulling me down. I could feel his dick jerking inside my ass when he suddenly pulled out a little. He was in that super sensitive state. I kept my body up about halfway and froze in that position. He moved in a little, then back out as he involuntarily spasmed in my ass. I knew he would be softening quickly so I lowered my self all the way moving back and forth in a last attempt to get off. I pushed my pelvis against his, trapping my little cock in between. Bob pushed up to help me as I finally shot my load in my panties.
As I raised myself up I could feel the wetness of some of his cum as his dick pulled from my asshole. We looked at each other with huge smiles. Bob pulled my head down to his and proceeded to give me a long wet kiss as he whispered, “You were great as ever. I have to visit the little boy’s room.” I rolled off of him onto my side while I tried to look at his dick to see if there were any remnants from my ass on it.
Once in the bathroom, I could hear the water running for a minute or so, followed by the toilet flushing, then the water, once again, for a few seconds. I figured this was a good sign that my ass was still clean putting my mind at ease. Bob got back in bed spooning me with his arm around me as we both fell asleep.
By the time we awoke on Sunday morning it was almost 10:00 am. Bob reminded me that he had to go to work at noon. I told him I would make breakfast while he showered and dressed for work. First, I went to the bathroom and peed before removing my negligee and putting on my night shirt. I left my bra and cum dried panties on. I could feel his dried cum around my hole as I walked into the kitchen. Then, I made pancakes as I enjoyed the feeling of last nights residual between my ass cheeks. When Bob was finished getting ready for work, we ate breakfast.
When it was time for him to go he asked if we could spend New Years Eve and New Years together. I told him I couldn’t think of anywhere else I would rather be. He gave me a long wet kiss as he rubbed his hands on my ass telling me to lock up when I leave. I walked him to the door and gave him a final kiss. I felt so much like a women at that moment.
After he left, I went to the bathroom, removed all of my make-up, and showered. As I rubbed the water on my skin I could feel it become slippery where his cum and my cum had dried. I used the body wash that Sis packed in my bag after washing my hair. When I stepped out of the shower I realized that I didn’t have any male clothes. I would have to dress as Joann and wait until Mom left for work before I could return home. That shouldn’t be a problem I said to myself. I looked through the remaining clean clothes I had left. There was one bra, a lacy thong, a pair of jeans, pink socks, and a tight white blouse. My breast forms were starting to pull off a little, but I knew the bra would hold them until I got home in the evening.
I put on the bra and thong, and then started drying my hair. After completing my hair and make-up, I pulled on the jeans and blouse, both were quite tight. They made my body tingle with every move I made as they caressed my legs, ass, and breast forms. I got all my dirty clothes together and stuffed them into the carry bag. I cleaned up the bathroom, kitchen, and made the bed before leaving. I was glad all I had were women’s clothes. It felt so good to be wearing them. It was the longest I was ever dressed as a woman. I put on my last pair of socks and the pink sneakers before getting on my coat. I loaded everything in the car as I thought about what I would do for a few hours.
On the way towards home I saw a shopping center with a discount clothing store. I pulled in to look at clothes for me and maybe something for Sis since we both took the same sizes. I ended up spending three hours picking out and trying on clothes. They had a large selection and I wanted to start expanding my wardrobe. It was 5:00 before I knew it, so I headed for home. Mom’s car was gone so I knew it was safe to go in dressed as Joann.
As I entered the house, Sis came running out of her bedroom. I told her, “I need to get these breast forms off. I’ve had them on since Friday.”
She helped me with my bag as she replied, “You know you’re not supposed to keep them on overnight or in bed.”
“I know. But they felt and looked so great that I didn’t want to disturb them. I’ll tell you all about my weekend while I get undressed.” We went into Sis’s bedroom where I took off my jeans and blouse.
Sis looked at me and said, “I remember when you wouldn’t let me see you in a bra. Now you’re standing there in only a bra and a thong without a thought about it.”
“That’s your fault,” I laughed, “Help me with this.” She unhooked my bra and I let it fall to the floor. My breast forms were peeling off at the top. Sis put her fingernails under them and started peeling them off my chest. Then she got the adhesive remover and sprayed it on. She went and got a wet washcloth and wiped off my chest. My skin was red from the extended wear of the breast forms. Sis rubbed some lotion on my chest and then got a heavily padded bra. She helped me put the bra on along with a soft night shirt.
We sat on her bed as I described my weekend with Bob. I told her we were going to spend New Years together. Sis responded, “Maybe we can double date. Michelle and I are going to a New Years Eve party at a club near the College. Please, think about it.”
“Okay”, I replied. “I’ll talk to Bob and let you know.” Little did I know that the New Year would bring so many defining events in my journey to becoming Joann. Well, that’s for the next chapter.
