Chapter 3: Becoming Joanie
The next day, Dottie picked out another pair of panties for me to wear under my male clothes. It was just as silky as the pair from the previous day and between the memories of the night before and the feel of the panties, I was hard most of the day. Dottie said she had to work for a while, and disappeared into her office while I worked around the house. After an hour or so, she reappeared.
“I need to run to the store,” she said. “I need to pick up some things. I’ll probably be gone a couple of hours.”
I gave her a comedic pout, then gestured to the hard lump in my pants. “Before you go….” I let my voice trail off.
She giggled. “You’ll just have to wait till I get back. I want you ready and roaring to go. And no jerking off!” she admonished.
I sighed, then gave her a smile. “No guarantees, but I’ll try,” I said.
She walked up and hugged me, then her hand slipped between us and gave my dick a few quick strokes. “It’ll be worth it,” she said. “Trust me.”
She slipped out of my arms and left. Over the next thirty minutes, I finished up the household chores and got bored. Idly, I wondered what Dottie was working on on a Sunday and went into her office. Her computer was on and not locked. I glanced at the screen but the only program I saw running was a chat program. I looked closer and saw that she had been chatting with Cathy. I scrolled to the beginning of the chat and began reading.
DMunro212: “So?”
CattyCathy: “Jim loved it. He thought John was amazing.”
DMunro212: “Good! John said he loved it too. I thought he would, after what he said about fantasizing about guys.”
CattyCathy: “That’s good. How soon can you get him to start dressing?”
DMunro212: “He’s been wearing panties for two days now. I’ll have to buy him up some clothes of his own. I know his sizes. I can’t wait to see him as a girl!”
I felt a little shock when I read that Dottie wanted me to dress like a woman. The idea shocked me and intrigued me at the same time. I tried to imagine myself as a woman, and the mental image wasn’t very appealing. I continued to read, but their conversation devolved into work-related stuff. I skipped all of it, and then came to the end of their chat.
CattyCathy: “I have a naughty idea. Can you get out of your house for a couple of hours?”
DMunro212: “:D Should I come over?”
CattyCathy: “No. 🙁 My niece is here visiting. She doesn’t know about you and me yet, and it’d probably freak her out. Maybe go clothes shopping for John? I could meet you at the mall.”
DMunro212: “Ok. I’ll leave here in a few minutes.”
CattyCathy: “I’ll see you there :)”
That was the end of the chat. I wasn’t sure I was liking where all this was going but at the same time it was exciting and erotic. All the fantasies about men replayed in my head, but this time I was dressed as a woman.
My dick was hard in my panties as I tried to take my mind off Dottie’s chat with Cathy. I had told Dottie that I wouldn’t jerk off, but I was just about to say the hell with it when the doorbell rang. I stood up, trying to arrange my hard dick so that it wouldn’t be so visible, then answered the door.
It was Jim. I was surprised to see him and just stood there with a confused look on my face.
“Can I come in?” he finally asked, bringing me back to my senses.
“Oh, sorry. Sure!” I stepped aside and allowed him in, then closed the door behind him. I don’t know why I would even think of doing it, but I locked the door behind him, then followed him into the living room.
“So what brings you over?” I asked, nervously.
“Cathy said she was going shopping with Dottie, so I figured there was no reason for both of us to be bored at home,” he smiled.
I knew in my heart why he had come over. I knew that I was going to end up on my knees, sucking his cock again and the idea excited me beyond belief. But, at the same time, it scared me. Dottie wasn’t here, this wasn’t just some playtime thing that she’d dreamed up. It almost felt like I was being unfaithful to her.
He walked up to me and stood there for a second, then gently put his hands on the sides of my head. Instinctively, I tilted my head back as he leaned in and kissed me. My dick, still hard in my pants, throbbed as our tongues dueled inside my mouth.
He broke the kiss and looked at me. “Are you still wearing panties?” he asked softly, running his hand down my back and cupping my ass.
I nodded.
“Show me,” he grinned.
I stepped away from him and quickly stripped off my clothes, then stood before him in only my panties. He smiled appreciatively, then moved behind me and pulled me close to him. I could feel his cock pressed in the crack of my ass, and my dick almost exploded right then and there. He started kissing my neck and his hand began playing with my nipples. My dick throbbed it’s approval of Jim’s actions. I don’t know why, but I pushed my ass against him.
His lips came off my neck and he pulled away from me. I turned around to see what he was doing and saw him stripping his clothes off. The previous night, I’d only seen his cock, but today I was seeing all of him. He wasn’t muscle-bound like the men in my fantasies, but he was definitely fit. I reached out and put my hand on his chest, sliding it down to his taut stomach, then even further downward to grasp his hard cock. He smiled at me and put his hands on my shoulders, pressing down slightly. I sank to my knees, his hard cock becoming level with my face.
“That’s my girl,” Jim murmured as my lips parted and his cock slid between them. The excitement I’d felt when I sucked his cock before was tripled because it was just him and me and that he’d called me his “girl”. I took him deep, fought off a gag, then got him even deeper. I could feel his pubic hairs tickling my lips.
“Ah shit,” he grunted between clenched teeth. “You really haven’t sucked cock before me?” His hands wound around my head, and feeling him start to take over, gently pushing his cock in and out of my mouth. My own dick throb in excitement.
“Mnnhh uhhhh,” I mumbled around his cock. I was SO turned on by the feel and taste of him in my mouth. We moved in synch, his cock and my mouth, as the blowjob I was giving him got faster and hotter.
“Yesssssssss, baby,” he groaned, “Almost…”
A second later, he gave an explosive grunt and my mouth was filled with his thick, tangy cream. Abstractly, as if it was off in the distance, I felt pre-cum seep from my dick as blasts of cum came from him, coating the back of my throat and insides of my cheeks. I swallowed, then swallowed again as I kept up my hungry oral assault on his cock.
His cock, spent, began to soften in my mouth. He tried to pull it out but I fought him, wanting him to stay in there and get hard again so I could make him cum a second time. Eventually, though, he prevailed and managed to pull out. I stayed on my knees, looking up at him.
“Damn you’re good,” he said, pulling his pants back on. I didn’t respond, but I know I had a disappointed look on my face.
He saw my expression and laughed. “Oh, don’t worry, there’ll be more. In fact, I can’t wait to have you for a whole night,” he said, finishing dressing.
“That sounds…wonderful,” I replied, slowly getting to my feet. I was still in a sexual daze, and all I wanted was more of his cock. He gave me a kiss on my cheek and a wink, then he was out the door.
I had to get off, was desperate to cum. I stumbled back to the bedroom and laid down on the bed. I quickly stroked myself to an intense orgasm, reliving the sensations of having Jim’s cock in my mouth. I dozed off, sated.
I was woken up unexpectedly by Dottie and Cathy. Dottie had a semi-disgusted expression on her face, Cathy had a grin on hers. “I knew you wouldn’t be able to keep it in your panties,” Dottie said.
Cathy laughed. “I told you that Jim would come by while we were out. Looks like he did.”
I vainly attempted to cover myself up with the sheet, but Dottie stopped me. “Go take a shower,” she said. “And shave again. I like you smooth.”
I was in the shower long enough that the water went from hot to tepid by the time I got done washing and shaving. I wrapped a towel around me and stepped back into the bedroom. They had obviously taken advantage of the time I spent in the bathroom, both of them nude and lying on the bed, Dottie curled up against Cathy’s side, idly stroking her nipple with her fingers.
“Uh, maybe I should come back later?” I ventured. I was kind of surprised that I wasn’t upset at the sight.
Cathy stretched languidly and said, “No, it’s fine.” Dottie rolled away from her and stood up, with Cathy right behind her.
Dottie walked up to me and handed me a shopping bag. “I want you to try something,” she said.
“I know,” I said. “You want me to dress like a girl.”
She blinked. “How did you know?”
“You left your chat up on your computer,” I replied.
“Oh, bad girl!” she giggled. “Peeking at my private stuff.”
I shrugged, then smiled. “‘Bad girl’, yourself. You could have talked to me about it first, you know.”
She pouted. It was really cute. “I was afraid you’d say ‘no’,” she said. “Are you?”
I looked at the two of them. Dottie had a hesitant, apologetic look on her face. Cathy, however, was leaning slightly forward with an almost predatory expression on her face.
Without intending to, my mind flashed to Jim calling me his “girl.” My dick stiffened, and Cathy giggled when she saw it start to rise.
“I think he likes the idea,” she said to Dottie.
“Then lets get to it,” Dottie said with a laugh.
Thirty minutes later, I was standing in the middle of the bedroom looking at myself in the big mirror. I had panties and an A-cup bra on underneath a skirt and a blouse, a raven-colored wig, and my face had been made up by the girls. I thought I looked amazing. I could still see ME in the reflection, but if I hadn’t known it was me, I’d swear I was looking at a young woman.
“We need to show Jim,” Cathy said excitedly. Before I could protest, she took her cell phone out of her purse and snapped several pictures.
“Uh,” I stammered. “I really don’t want this to get out.”
“It’s just Jim,” Cathy replied with an impish grin. Her phone dinged and she laughed as she read a text message, then showed it to me.
“WOW!” Jim had sent. “MORE!!”
“Get on the bed,” Dottie suggested. I got on the bed, kneeling, and Cathy took more pictures. It turned into an impromptu photo shoot, with my poses becoming more and more suggestive.
I was really getting turned on by it all, especially by Jim’s texted replies to the pictures that Cathy sent him. I gave Dottie a suggestive look. “Feel like going lez with me?” I grinned, ignoring Cathy.
Without a word, she pushed me onto my back on the bed, then straddled my head. She was already wet, and my dick throbbed when she lowered her pussy against my lips. As I hungrily licked her pussy, I could feel Cathy raising my skirt up and pulling my panties down to expose my raging-hard dick. A few seconds later, I felt her straddle me and a hot, wet pussy slide down my cock.
I jerked. I wasn’t supposed to fuck Cathy! Having her mouth on my dick in the heat of the moment was one thing, but Dottie was the only woman I wanted to fuck! I shifted underneath them, trying to throw Cathy off of me as I made muffled sounds of indignation in Dottie’s pussy.
“Relax, it’s ok,” Dottie moaned, grinding her pussy hard against my mouth. “Cathy and I talked about this.”
I slowly relaxed as Cathy started raising and lowering herself onto my dick. I tried to concentrate on Dotty, my tongue getting wilder and wilder until I felt her pussy contract as she gave a hard grunt, then a moan. Almost at the same time, I felt Cathy’s pussy grip my dick rhythmically and heard her soft moan of pleasure.
Just a few more seconds, I thought, pushing my hips up, trying desperately to cum. Before I could, however, Cathy pulled off of me and rolled over onto the bed. A few moments later, Dottie moved away from me. I laid there, frustrated. My hand grasped my dick and I started stroking it until Cathy playfully slapped it away.
“No time for that,” she said. “Jim’s bringing dinner. Fix your make-up, you look a fright.”
I groaned, but did as she said. My make-up was smeared all over my face, and Cathy helped me clean it off and reapply it while Dottie got dressed. It took a long time for my dick to go down, and even when it did there was still a low growl of lust inside me.
Jim showed up with Chinese, and seemed fascinated by my appearance. He sat next to me in the dining room while we ate, and couldn’t keep his hands off of me, sliding his hand up and down my thigh or caressing my back. I had to admit, I enjoyed the attention and the sensation of his hand on me.
After dinner, I picked up while Jim and Cathy went into the living room. Dottie stayed to help me pick up.
“They’re staying here tonight,” she said, a bit of apprehension in her voice.
“Ok,” I replied. “The guest room is made up.”
She seemed to want to say something else, but didn’t. She left and I took a few more minutes finishing up the kitchen.
When I went into the living room, Dottie was on the love seat with Cathy again. Jim patted the couch next to him and I sat. He put his arm around me.
“You girls did a wonderful job,” he grinned, looking me over. “I didn’t realize how beautiful you could make her.”
I blushed at the compliment, and my dick twinged at being called “her”.
“It was easy,” Cathy said. “It was already there, we just had to bring it out.”
She whispered something into Dottie’s ear, then the both of them stood up. Dottie smiled at me a bit nervously then Cathy took her hand and led her to our bedroom. The bedroom door shut with a loud click.
As I sat there, confused, Jim leaned over to me and nuzzled my ear. “I guess that’s the signal for bedtime,” he murmured. “Now where’s that guest room?” He stood and held out a hand to me.
I suddenly understood what was going on. Jim and Cathy were staying alright, but they weren’t using the guest room. My hand trembled as he took it and he slowly pulled me to my feet. I felt like I was in a dream we walked to the guest room. The sound of the door closing behind us seemed very loud.
I was too scared to be excited and too excited to be scared at the same time. Jim slowly helped me take my blouse and skirt off, then stood back and admired me in bra and panties. “Jesus, you’re hot,” he smiled, then pushed me gently towards the bed. I fell backwards onto it and he move on top of me.
His lips found mine, and we shared a passionate kiss as I felt his weight settle on me. Honestly, I could have orgasmed right then and there just from the erotic sensation of having a man on top of me. He shifted, raising up slightly and scooting down my body, then pulled my bra up to expose my nipples. His mouth worked magic on them, sucking and biting them gently as I squirmed in excitement underneath him.
He worked my little titties for a long time, then abruptly raised up off of me. I looked up at him, startled, but he just winked.
He quickly stripped off his clothes. Kneeling on the bed next to me, he gently pulled my panties off and threw them on the floor. After nudging me to the middle of the bed, he crawled between my legs.
I knew what was coming next, dreaded it and hoped for it. He grabbed a bottle of lube on the nightstand (where did THAT come from??), and coated his beautiful cock. He used his finger to lube my asshole up, which both tickled and excited me.
“Do you want this?” he said quietly. “Do you want me to fuck you and make you my girl?”
I had never been more turned on in my life than I was at that moment. “Yes,” I said breathlessly.
My ankles went up onto his shoulders, and I felt the tip of his cockhead press against my waiting asshole. I felt a twinge of pain when he began spreading me open, but I expected it. From the few times that Dottie and I tried anal, I knew there was some pain involved but I was so turned on that I didn’t care how much it hurt. I wanted him deep inside me.
He was gentle and slow, pushing into me then stopping to wait for me to adjust and relax. A quarter of his cock was inside me, then half. Finally, I felt his groin press up against my asscheeks.
“Ohhhh,” I moaned. It was still a bit uncomfortable having him completely inside me but nothing I couldn’t handle, and to be honest the sensation of being underneath him, being TAKEN by him, was more exciting to me than the physical sensation of being penetrated.
He pulled out an inch, then pushed back into me hard. I grunted in pain/pleasure, willing myself to relax more. As I did, the sensation of his shaft sliding into my asshole became more pleasurable. He pulled back again and I surprised myself by pushing my hips up to meet his next thrust. That felt even better.
“Yes, baby,” he groaned, his thrusts becoming faster. “I love it when you fuck back.”
My dick was leaking copious amounts of pre-cum as he fucked me hard and fast. The longer it went, the better it felt. The headboard of the bed was slapping against the wall from the force of his thrusts.
“I’m gonna cum,” he said breathlessly. “I’m gonna fill your pussy.”
My dick throbbed at his words. I wanted him to fill me, wanted his juices deep inside me. “God, yes,” I moaned.
His thrusts developed a little sideways twitch and in the back of my mind I recognized that he was close, really really close.
“Are you my girl, Joanie?” he grunted.
“YES,” I moaned loudly. In the midst of being pounded by his wonderful cock, of course my name was Joanie.
If he was going to say something else, it was lost when slammed his cock as deep into me as it would go. I felt it throb inside of me and he started cumming deep in my ass. My dick pulsed, threatening to cum with him, but not quite reaching that height.
He twitched, straining against me, while his orgasm ran it’s course, then slowly relaxed. I groaned in frustration as his cock slid out of me. He quickly rolled off of me to my side, then his hands urged me to lay on my side facing away from him. As soon as I did, he slid himself back into me. I could tell he was softening, but he was still hard enough.
“Stroke your clit, baby,” he said from behind me, his hand sliding over my side and cupping one of my breasts. “You need to get off too.”
It didn’t take very very long. The eroticism of his cum-coated cock in my ass combined with the feeling of his hand on my breast, combined with the excitement from being fucked for the first time, made my orgasm one of the strongest I’d ever felt. I was actually out of breath when it finally ran it’s course.
I laid there for a long time, completely sated and basking in the feel of his warmth behind me, his arm over me. I gave a whimper when his cock finally softened enough to fall out of my ass and felt his juices slide out of me and down my asscheek. I listened to his breathing get slower and softer. I was wondering if he was asleep as I drifted off myself.
I woke up slowly, confused as to where I was, then remembering that I was in the guest room. I glanced over…no Jim. Another glance at the clock on the nightstand told me it was almost 7AM. I could feel the ache in my ass and the dried cum on my asscheeks from last night as I sat up in bed. The sensation brought an unexpected smile to my face.
I got up, picked up my panties off the floor and walked to the bathroom. I relieved my bladder, then looked at myself in the mirror. My make-up was a mess, and at some point last night the wig had come off. The bra straps were twisted, so I fixed them and put my panties back on. I needed a shower, but I needed coffee more.
Dottie was waiting for me outside the bathroom. She had an expectant grin on her face.
“So?” she asked.
I was embarrassed to admit it. “It was incredible.”
She giggled. “I bet. Cathy and I thought you two were going to break the bed.”
I smiled. “That loud, huh?”
“That loud,” she confirmed with a smile, turning towards the kitchen. I followed her. We sat at the kitchen table, drinking coffee.
A thought popped into my head. “You put the lube in the guest room, didn’t you?” I asked.
“Yes,” she admitted.
“So you knew this was going to happen,” I said. “You set all this up.”
“Yes,” she again admitted. “But you liked it, right?”
“Yeah,” I replied. “I did.”
“Was it a one-time thing?” she asked me after a pause.
“What do you mean?”
“Do you want to keep doing this…with Cathy and Jim, I mean.”
I pondered her question. There was no denying that I loved being fucked by Jim and sucking his dick really excited me. I like the way he treated me, looked at me, when I was dressed as a girl. I wasn’t threatened by Cathy, didn’t feel like she was going to take Dottie away from me, and Jim didn’t seem to have much interest in Dottie, only me, so I didn’t feel threatened there either.
“Yes, I think so,” I replied slowly. “I just have one request, though.”
“What?” she asked.
“No more surprises,” I said. “You surprised me by setting me up to suck Jim’s cock, and surprised me with spending the night with him. And you tried to surprise me into dressing like a girl. I love you, but I really don’t appreciate it. We used to talk about things before they happened.”
Her face turned a bit red in embarrassment. “I know, and I’m sorry,” she said. “I didn’t know how far you would go if you thought about it first. But you have to admit, you liked all of it, right?”
“Yes,” I agreed.
“Let’s go get cleaned up,” she said, finishing her coffee and standing up. “We’re going to Jim and Cathy’s house for lunch.”
“Don’t you work today?” I asked, glancing at the calendar to confirm that it was Monday.
“Cathy and I took the day off,” she said.
The shower was long and sensual, washing and shaving and teasing each other’s bodies. I made her cum with my finger, stroking her clit from behind her. She returned the favor on her knees under the warm spray.
After drying off, we moved to the bedroom. I opened my dresser drawer and pulled out a pair of my underwear. Dottie stopped me.
“No,” she said.
“No? No what?” I asked, confused.
“They didn’t invite John and Dottie for lunch. They invited Joanie and Dottie for lunch,” she explained.
A lump formed in my throat. “WHAT??” I said, not completely comprehending what she said.
“You’re going as Joanie,” she answered calmly.