It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?”
I answered, “Out with the boys, Sis.”
“I hope you don’t mean what that sounds like.”
I responded, “If it sounds like I had sex with multiple men at the same time, then that’s what it means. I didn’t realize Joann was such a slut.”
Sis motioned to me, “Sit and tell me about your night. I miss sitting together on the couch like we always did.” I told her I was going to get into something more comfortable and would come back to join her on the couch. I went into my bedroom and took off my dress, my bra, and my breast forms. My ass cheeks were still squishing from the lubrication from being fucked twice and there was still a condom hanging out of my ass so I left my thong on and put on a shear teddy. I went back into the living room and sat next to Sis.
She put her arms around me as she said, “Just how many men did you have sex with? Did you practice safe sex?” I told her the details about my first gangbang. I assured her that I was careful in my interactions with men. I told her this soccer league offered an opportunity to meet men who already knew I was transgendered, generally avoiding the dangerous situations I had read on the internet and seen on the news. As I was talking, Sis was rubbing her hands on my arms, then on my chest. “You’re starting to develop breasts. I guess that’s from the hormone treatments. How do you like them?”
I responded, “I don’t think they will ever fill a “B” cup, but they are becoming more sensitive. I think I’ve gained two inches on my bust and two inches on my hips. Do they feel bigger?” This prompted her to rub them with her finger tips causing me to let out a quiet moan. As she continued to message my nipples I involuntarily arched my back laying the back of my head in her cleavage. She leaned her head down and licked my right nipple with her tongue. I couldn’t believe or control my reaction. I rolled over and sat up in her lap, pulling my nightie up over my chest, while pushing my right nipple to her mouth. As she softly sucked on my nipple, I started going crazy. I didn’t realize how high my sensitivity had become.
After a few minutes of me hugging her head and moaning like a girl, Sis switched to my left nipple muttering, “I guess those hormones are having an effect on you.” I continued lightly moaning almost to an orgasm. Suddenly, I felt her hand wrap around my cock as she gently jerked me off. Within minutes I shot my load into her hand. She raised her cum filled hand up to my mouth. I licked it clean as she whispered, “Can you take care of me, now? Michelle had to go away for work for a few weeks.”
Before I could answer, she was pulling her toys from the cushion under her. I pulled her down on the couch so she was lying on her back. I took the large dildo and started pushing it into her pussy until it was completely in her. Then, I took the vibrator, rubbed it with warming lotion, and inserted it slowly into her ass with only the control knob sticking out, before turning it on. As she started to wiggle, I pulled up her sheer nightie and began to suck on one of her nipples. She reacted the same way as I did when she was sucking on my tits. She pulled my head tight against her tit as she let out a long moan. After a few minutes, I switched to the other nipple prompting another long moan as her hips were bucking uncontrollably. I’m sure I gave her multiple orgasms. Then I moved down her body and started licking her clit with my tongue at a furious pace. Her moaning became quite loud and she was pulling my face into her pussy almost breaking my nose as she reached another orgasm.
When she finally relaxed a little, I realized that the dildo was completely buried in her pussy. I had to reach inside her with my thumb and forefinger to grasp it on the end. It was too slippery at first, so I had to pull my hand back a little and push in two fingers and my thumb to get enough grip to pull on it. This sent her into another orgasm as she grabbed her pussy lips with two of her fingers and pulling the dildo out of my grasp. Finally, in desperation, I just pushed my whole hand into her cunt, using my thumb and all of my fingers to hold on to it, pulling it out of her. She grabbed my hand and pulled the dildo to her mouth licking it like I lick a dick. I was dripping, myself, watching her, as she continued to hold my hand in hers as she guided it around her mouth.
I placed the dildo on the coffee table when I realized the vibrator was still in her ass. I reached between her legs turning if off, before pulling it out and setting it on the table, also. She said, “Thank you, Joann. I’m just going to lay here like this for a while. You can go to bed. I’ll clean up in the morning.” I got up and walked to my bedroom. My ass was still a little sticky from my lube drenched thong bringing back my memory of first gang bang. I went to bed and fell asleep with my thong still on and a condom in my asshole.
The next morning I got up, pulled out the condom, showered, washed my hair, and shaved my legs. I put on my girdle gaff, a pair of tight shorts, and a halter top with a strapless bra and adhesive breast forms. I ate a light breakfast before sitting at my desk and writing three programs for the day. Sis came home and made dinner. As we were eating, she reminded me that the grass needed mowing. In the past, I would put on my Joseph clothes to mow the lawn. However, it had been three weeks since I was Joseph and I didn’t feel like changing. I went into my bedroom and put on my pink sneakers and lace topped socks.
Sis looked at me as I walked toward the door, “Is Joann mowing the lawn? Do you think that’s a good idea?”
“Why not,” I asked. Sis just smiled and shrugged as I went out the door into the garage. I pushed the button to open the big garage door and pushed the lawnmower out into the front yard. I couldn’t believe my excitement. I’ve been outside as Joann many times in the past year, but this was different. It was day, I was out in the open, and I was in my own front yard. I felt like I was coming out of the closet. I started the lawnmower and began mowing the yard. At one point, I noticed the neighbor across the street watching me as he was mowing, too. I waved to him and he waved back.
When I finished mowing, I put the lawnmower back in the garage and got a broom to sweep the sidewalks and driveway. I was enjoying myself working in the yard as Joann. It was good practice at walking, bending, and moving around as a woman doing normal things. Suddenly, I heard a voice, “Hi, Amanda. How have you been?” I was caught by surprise. The neighbor across the street had walked over while I was bending to pull up some loose grass.
I quickly thought as I answered, “Hello. Amanda is my cousin, I’m Joann. How are you?”
“I’m sorry. I’m fine. I’m Bill, I live across the street. I saw you mowing and thought you were Mandy. We’ve been neighbors for ten years, but rarely get to talk anymore.”
Sis must have seen us outside and thought she should come to the rescue, “Hello, Mr. Simpson. It’s been a long time. How are you?”
I quickly jumped in, “Hey cuz, Bill thought I was you.”
Bill responded, “I’m good Mandy. It has been a long time. Joann is as pretty as you. It was an easy mistake. How are your mother and brother?”
Mandy told Mr. Simpson that Mom and Joseph moved at the beginning of the year and that I moved in to keep her company. I thought it was a convincing story. He told us that he and his wife separated a few months ago. The entire time we talked I could see his eyes constantly looking down at my crotch. He was probably in his mid to late forties and was clearly interested in me. He finished our conversation with an offer to help with anything if we found ourselves “damsels in distress”.
Mandy helped me finish cleaning up and putting away things in the garage. She commented that she also noticed Mr. Simpson’s attention to my creative feminine feature. Then she complimented me on my quick thinking with the cousin story. I told her I was concerned that too many people would know Joann before Mom. Maybe it was time to tell her. We agreed to think about it for a while.
A few nights later, Chrissy, from my soccer team, called to tell me this Monday was “Gurls Night Out”. All of the gurls would go to a bar after practice. I was both excited and disappointed. It would be fun to spend time with the gurls, but I was hoping to see Donny, again. My social life was finally beginning to bloom.
Sunday night, as usual, I started to pack my bag with clothes to change into after practice. I wasn’t sure what to wear to be with the gurls. I called Chrissy and she said she was going to wear a short dress. I went into my closet and picked out a strapless one-piece short white dress with red trim. It was light and comfortable, sexy, yet not to showy. It was perfect for the occasion. I packed a strapless bra, bikini panties, and 3-inch high heeled sandals. My legs had a nice tan and this would show them off well.
Monday afternoon I changed into my soccer outfit, grabbed my bag, and headed out the door. Bill was sitting on his front porch and waved to me. I waved back as I was getting into my car. During practice I noticed the absence of spectators. Chrissy explained that “Gurls Night Out” was a regular monthly event, so no boys came to try their luck afterward since we all left together. The practice went fast since we divided into two teams and played against each other, which apparently was aligned with the night out. Afterward, everyone went to the showers, cleaned up, and changed. I received compliments from everybody as I walked back into the locker room after changing. Coach June even gave me a little slap on my ass as she said, “Very nice, young lady.”
Chrissy told me to follow her in my car to the bar. As it turned out, it was the same bar Donny and I went to a few weeks earlier. Chrissy said they go to this bar since it has an outside deck that can be accessed from the parking lot. Some of the gurls are not too passable, so discretion is important. The deck had three levels and we had the one to ourselves. As we sat and ordered drinks and snacks, I realized how comfortable I had become as Joann. Most of the others did not pass as a woman like Chrissy, June, and I. A few of them were actually pathetic. I wondered if they had someone like Sis to help them out.
Once the drinks arrived and the conversations began, many questions regarding my transformation were being directed at me. Three or four of the gurls told me how good I looked and wished they could be so passable. I explained how Sis taught me to do my hair, make-up, and nails. I told them that every little detail was important. After an hour or so of being the center of attention, I couldn’t believe I offered to have the next “Gurl’s Night Out” at my house. My journey to becoming Joann was reaching a new level. I think every gurl gave me a kiss and a hug as we left for the night.
When I got home I couldn’t wait to tell Sis about my night. Although she had mixed feelings about me inviting the soccer team over when I first told her, she was thrilled after she thought about it. She realized how much I appreciated her over the past few years. It would also be an opportunity to practice her art on such challenged gurls. At the end of our conversation, I went into my bedroom and took off my dress. Sis came in with a box and said, “I got some new sleepwear in the mail today. Do you want to try one of my silk nighties on? They are so comfortable in the summer.”
I replied, “Thank you, Sis. Could you unhook me?” I turned around so she could unhook my strapless bra. Then she helped me remove my breast forms. We went to the bathroom so I could remove the adhesive with spray remover, clean my breasts, and apply some lotion. I took off my bikini panties and Sis handed me the silk thong. It felt so good as I pulled it on. The bra was also silk and sent chills through my body as it rubbed against my exposed nipples. I was in ecstasy as I pulled the nightie over my body. It, too, was silk causing it to glide against the silk bra and panty.
Sis took me by my hand into her bedroom as she asked me to help her change, too. I helped her pull off her t-shirt and unhooked her bra. She put on her silk panties, bra, and nightie, and then said she had silk sheets on her bed and I should try them. When I laid on the bed it felt cool and slippery. Sis said, “What do you think?”
I replied, “It feels wonderful.”
She laid down next to me with her arm around me and her hand on my breast. As she rubbed my nipple lightly with her index finger she said, “Don’t even think of cumming in this silk. It doesn’t clean up well.”
“Then why are you rubbing my nipple”
Sis answered, “It reminds me of Michelle. It gets so hard and sticks out when I rub it.”
I couldn’t resist saying, “Are we still talking about my nipple?” She moved her hand off my tit and smacked me on the ass before resuming to rub my nipple. I fell asleep in her bed with a hard-on.
When the weekend rolled around I decided to start cleaning up the house so it would be ready for “Gurl’s night” next month. I went through the garage and looked for something to trim the sidewalk edges. There was a straight shovel that looked like it could do the trick. I opened the garage door and started on the driveway. While I enjoy working outside as Joann, I didn’t realize how hard it was to trim along the driveway and sidewalks with a shovel. As I was starting to get frustrated I heard, “There is a power tool for that.” I turned to see Bill Simpson from across the street standing behind me. “Let me go get mine. You’ll be all day doing this with a shovel.”
“Thank you, so much. I didn’t realize how hard this was.” Bill immediately went to his house returning with an electric powered edger and a long extension cord. He asked if there was an outlet outside to plug it into. I told him it would probably have to be plugged in the garage. We went in and I found a receptacle behind some boxes. I had to bend over to reach it. I could see Bill was looking at my ass. I looked behind me and smiled at him. Back outside he showed me how to operate it. When I started pushing it, sparks began to fly, literally, as the blade was hitting the concrete. Bill reached around me from behind and guided the edger along the driveway. I could feel his breath on the back of my neck.
As we moved along the driveway, he eventually let go as I’m sure we would be the talk of the neighborhood in that position. Bill found a broom in the garage and started sweeping the grass as it accumulated on the concrete. We switched back and forth edging and sweeping for over an hour until all the edges were complete when I told him, “Thank you, Bill. You really didn’t have to do all of that. Would you like something to drink? I have some homemade ice tea.”
He replied, “Thank you, that would be nice.” I opened the door in the garage and motioned him into the house. We went into the kitchen where I poured us both a glass of ice tea. Then, we went out on the back patio to sit on the recliners. We were both checking each other out. I could see him looking at my tight shorts while I was looking up his loose shorts. He didn’t have any underwear on and as he moved his legs apart I could see he was well endowed. I was getting excited at the thought of being so close to a big dick and was plotting in my mind how to work it to my mouth.
After some small talk, I noticed his glass was empty, so I asked if he would like some more ice tea. He answered yes, probably wanting to prolong our time together. When I returned with his drink, I accidentally spilled part of it in his lap. As I apologized I offered to throw them in the dryer for a few minutes. I suggested he go into my bedroom, take off his shorts, and put a towel around him while waiting for them to dry. He was only too happy to oblige me. After throwing his shorts in the dryer, I invited him to sit on the sofa with me as we waited. I sat down next to him with my leg against his. As we talked, his hand kept brushing my leg. Each time it did, I smiled. Finally, I took his hand in mine and held it on my leg as I said, “Thank you so much, again, for helping me this morning. I feel like I should do something for you.”
Without a word, he smiled back at me and started rubbing my leg. I took my hand off of his and rubbed his leg. Before I knew it, we were kissing each other. I reached down and loosened his towel. As we continued to make our intentions clear, I pulled the towel open before putting my hand on his beautiful dick. I had to have it. I rolled off the sofa and onto the floor between his legs. I put both of my hands around his shaft and the tip was still sticking out. I slyly exclaimed, “What a large dick you have Mr. Simpson.” I jerked him off a little with both hands, one above the other. When he started to drip a little pre-cum, I began licking the slit on his tip. I looked up at him as I continued licking.
When he moved his hands to my shoulders, I started to take his shaft into my mouth. I sucked it as I moved it in and out of my mouth. I began to wonder if I would be able to get such a big dick into my throat. My lips were stretched to their limit just to get it into my mouth. I pulled back to try to get more pre-cum for lubrication. Then, I worked up my saliva making the sloppiest blow job of my life. I was also making quite a lot of noise. It was time for the moment of truth. I took a breath, said “ahhhh”, and began to force it into my throat. At first it didn’t seem like I was going to get it down. It was getting stuck at the entrance to my throat. I pulled back, took another breath, and pushed, again. I had to start moving my head up and down trying to force it in. On the third try, my throat opened a little like my ass and down it went. I could feel his dick bending a little as it pushed in and my head pushed back. I started to gag.
I pulled it out to prevent throwing up and making a mess. I could hear Bill starting to apologize. This only made me more determined. I took a deep breath and pushed it down my throat, again, while I was still receptive. This time it went straight down my throat causing Bill to let out a loud gasp. I was able to move it in and out of my throat four or five times before coming up for air. His shaft was completely covered with my slobber and his slit was oozing pre-cum. I licked his tip and swirled my tongue all around it before I enveloped his tip with my lips then taking a few good sucks. I licked up and down his vein which felt like it was going to explode. Then I started down his shaft another time until his dick was against the back of my mouth. I pulled back far enough to take another deep breath before forcing it back into my throat. Although, his dick was bending somewhat to conform to my throat, it was still quite stiff and was causing a little pain as it opened it up.
Bill kept moaning and repeating, “Ohhhh yes!!!!!!” His hands were now on my head. When I pulled back up to breathe, I looked up at him, keeping his dick in my mouth the whole time. He was looking up at the ceiling with his head leaning back on the sofa. He muttered in an almost strained voice, “I can’t believe this.” I grasped the base of his cock and part of his balls using both of my hands as I moved my sealed lips up and down his shaft. I increased my pace giving him more of a traditional blow job. I would move down until he was at the back of my mouth, then move up to the tip of his dick where I would suck on it several times.
After a few minutes of moving up and down his dick, I let it out of my mouth and licked the pre-cum like it was a lollipop. Once, again, I looked up at him. This time he was looking directly into my eyes with a huge smile. He exclaimed, “Joann, you’re amazing.” I was thinking the same. I’d been working this huge dick for almost an hour without a sign of him releasing his cum. I put him back into my mouth and moved up and down several times rapidly before taking a deep breath forcing him into my throat until my lips were against my hands. I opened my hands as I pushed his dick further into my throat until my lips were against his balls. I was actually wet from my own pre-cum and must have been as excited as him. I just kept pushing him into my throat for ten or fifteen seconds. It was if I wanted to swallow his whole member into my stomach. I can’t describe the feeling of having a man inside me, be it my throat or my ass. Finally, I had to pull up for air.
Bill started to push forward. I thought he wanted to push it back into my throat, but he was actually standing up. What was he doing I thought? I looked up at him as he grabbed his cock and started jerking it off with his right hand. Then he actually asked the question that all my other lovers only thought, “Where do you want it?” I answered by opening my mouth wide. As I looked up at him I could see the expression on his face as it began to contort from the impending climax. He aimed his throbbing dick at my mouth as he let loose with his first load. It was the biggest and strongest shot I had ever experienced in my life. I started moving forward to take him in my mouth when the second load shot out as big as the first. My mouth was full and dripping. I had to close my mouth to swallow as another burst sprayed my face. I opened my mouth just in time for the last shot as I put his blazing shaft into my mouth. I couldn’t believe a man could cum like this.
His hand was still wrapped around his cock as I began to lick around it in my mouth. He slowly pushed his hand forward like he was emptying a tube of toothpaste of the last of its contents as he pulled back until the tip was outside my mouth against my lips. I stuck out my tongue to catch the last little drip oozing from his slit. Using his hand he rubbed the tip of his cock around my lips before pushing it into my mouth for one last licking. I could taste and feel his cum throughout my entire mouth. He put his hands around my head and pulled it tight against him. His softening cock was still long enough to enter my throat a little as he moaned out his last, “Oh shit.” Although my mouth and some of my throat was stuffed with his cock, its softness allowed me to breathe through my nose holding it there for a few minutes. I never felt so fulfilled from giving a blowjob as I did at this moment.
Bill relaxed his grip on my head leaving the decision to withdraw to me. After a few more moments of savoring his manhood in my mouth, I reluctantly pulled back feeling my biggest dick, so far, slither out. As he pulled back, falling onto the sofa, I realized that my face was coated with his cum. I used my tongue to lick what I could reach, before using my fingers to wipe the remainder to my mouth. Bill was watching and smiling as I cleaned up my face like a cat. I smiled back to express my satisfaction. I didn’t want to complicate things with any conversation other than, “Let me get your shorts, I’m sure they’re dry by now.” I knew I had to have that big dick in my ass one day, but I would have to give up my secret to him first.
I took his hand and brought him to the laundry room. I pulled out his shorts and held them open like I was dressing a child. He stepped into the shorts and I pulled them up, momentarily stopping long enough to kiss the tip of his dick once more before saying good bye. As I took him through the garage, he said, “I hope I can return the favor one day. Just knock on my door.” He gave me a big hug and kissed me on the forehead as he left. I went into the bathroom and washed my face before heading outside for more yard work. My throat was a little sore, a bittersweet result of my biggest dick, to date.
A few hours later, Sis and Michelle pulled into the driveway. Sis yelled to me, “Guess who’s back?” I could see the excitement in her face. Michelle ran over and gave me a big hug and a long wet kiss. Sis gave me a hug and kiss on the cheek. “The front yard looks great.”
I responded, “Thanks, Bill Simpson helped me with the edging. I want to start getting ready for Girls Night next month. Did you tell Michelle? I’m really hoping she will come, too.”
“Yes, I told her. She’s excited about it. You better watch Mr. Simpson. I think he wants to be more than just a neighbor.”
I just smiled at Sis, trying not to give things away. The three of us went into the house, made some snacks, and sat on the back patio to discuss our hosting Gurls Night, which would become one of the biggest events in my becoming Joann. Stay tuned for Stage Ten, the defining turning point.
