tagTransgender & CrossdressersBusted Wearing Panties Ch. 03

Busted Wearing Panties Ch. 03


I was in a deep sleep dreaming about Jessica and Chris, our naked bodies intertwined. I wanted to play more but the ringing in my ears kept getting louder and louder. My eyes flew open as it registered that the phone was ringing. I sat upright in bed and fumbled for the phone on the nightstand.

"Hello?" I managed as I put the receiver to my ear.

"James did I wake you again? My timing is perfect isn't it?" A smile crossed my face as I heard Emily's voice.

"You did, but its great waking up with a smile on my face after hearing your voice." Even half asleep I still got it. What a silver tongued stud I thought to myself.

"Well then, I need to call you more often. Mom is healing better than expected I should only be here another day, maybe two. I have her setup to receive around the clock care for the next couple of weeks then she should be back to normal. I really have to consider another place for her."

"Some of the assisted living communities are nice. She still has her wits about her. She just needs someone close enough in case she falls. There are some nice ones that serve meals and will take her to appointments. She will meet new people and make new friends. We should look for one around here so we can also be around more." Wow, I'm on a role.

"James you have me so fucking hot for you right now I think I have to go change my panties." When Emily said that I felt my face flush because I was thinking the same thing, I need to change my panties as well.

"Well it's a work day so you better get up now, unless you already are?" Emily was not playing nice.

"I am now, thank you very much. I guess I will have to deal with this one on my own." I retorted back.

"Just as long as you leave some for me when I get home because I can guarantee that I will rape you. In fact, I think I will call Jessica when I leave here to tell her to get the hell out of the house because I know I will be screaming. I can't wait to feel your cock filling my pussy." I could tell that Emily was getting heated by the fact that her breathing became deeper.

I grabbed my cock and started to stroke it. Emily's voice was getting to me, "You're making it hard to wait for you. I'm going to take care of things now."

"Oh James yes, stroke your cock for me baby. I'm so horny, I need you so bad. I'm actually fingering my pussy thinking of being with you. I need to hear you baby, stroke your cock." Emily wanted phone sex and I was eager to comply.

I was horny and wanted to pound one out, what better way than with your wife's permission. "Oh Emily I'm so hard. You're going to make me cum. MMMMM!" I feverishly started to pound my cock.

"That's it baby pull on that cock. Feel how hard your cock is in your hand. MMMMM, I wish I was there now licking the tip as you stroke your cock. Bringing a nice drop of your cum up to your mouth so that we can savor it together with a nice kiss. I want to lick and suck your balls as you pull on your cock. Oh baby jack that cock." Emily began to talk faster as her orgasm was beginning to peak.

"Oh M, fuck yes. I'm jacking off for you baby. I'm going to shoot my cum all over my stomach. You have me dripping like crazy. UGGHH!" I was really pulling on my cock watching the skin cover the head of my cock then reappear as I pulled the skin back down. I grabbed my balls and pulled them away from my body causing the skin on my cock to pull tight and the head of my cock to glisten with precum.

"Lick it off for me baby. Grab that precum and let me hear you suck it off your finger. MMMM! Hurry baby eat it." Emily's voice was ragged as she spurred me on.

I grabbed a drop of my cum and brought my finger to my mouth. I was sure to make loud sucking sounds for her, "MMMMMM! It tastes so good baby. MMMMMM, nice fresh cum being licked from my finger like sucking a little cock." I got caught up in the moment and didn't realize my confession.

"That's it baby suck that cock, lick that cum off. Is that it baby you want a cock in your mouth? That would be so hot to watch you suck a cock and have it shoot fresh hot cum into your mouth. MMMM Oh god I'm cumming, mmmmmm AAAGGGHHH!"

Emily pushed herself over the edge talking about me sucking a cock and it was enough to send me over as well, "AAAGGHHHH, MMMPPHHH! I'm cumming too baby. Shooting cum all over me." I lost control.

"Quick baby scoop it up and eat it, lick it off your finger. Taste your cum baby." Emily was shouting orders at me.

I obediently obeyed as I scooped up a thick glob from my stomach and greedily sucked it into my mouth, "MMMMMM. Tastes so good. MMMMM"

Emily was having a wild orgasm as she panted out her orders, "Ya baby suck that cum off that cock. OH SSSHHHIIITTTT! Eat that cum you little cocksucker. NNNMMMMM!!!"

We both calmed down a bit, "M, that was fucking hot. I have never gotten off on phone sex before. Come home fast." I panted out to her.

Emily giggled back at me, "YOU better not cum fast. I need a good long fucking. That was intense. I can't wait to spend the day in bed with you and find out what else we can fantasize about, that one got me hotter than I thought. Now clean up and do all your work I want nothing in our way when I get home. Love you."

"Love you too, bye." The phone clicked and I let the receiver drop to the bed. My head fell back against the pillow as I took a deep sigh. I lay there slowly running my finger through the pool of cum on my stomach, raising it to my mouth, and licking it off my finger until it was all gone. I got up and showered.

I slipped on the blue baby doll outfit and went to the kitchen for my morning cup of coffee. Chris was sitting in a nice grey suit sipping his coffee and eating a piece of toast. I poured my coffee and sat next to him.

"Good morning, where's Jess?" I asked Chris.

"She headed off to school already. I have to take off in a second to show a house. What's on your schedule?" As Chris spoke I naturally glanced down to his crotch and noticed his cock pressing out against his pant leg.

I reached over to him and stroked his cock through his pants, "Seems everyone is up early this morning. I'm just going to hang out finishing some work and then I thought I would try and add to my 'all over' tan." I then gave his cock a couple of little pats before sitting upright and taking a sip of coffee.

"Damn. I have to get off....I mean take off, and show this house. I'll be back later maybe I can join you? Jess will be at school for a while she has a group meeting this afternoon." Chris got up and, as he took his cup to the sink, ran his hand over my chest, stopping long enough to tweak my nipple. I took a deep breath between my clinched teeth as he sent a tingling sensation all the way down to my balls. Chris rinsed his cup and headed out the front door.

I took my coffee back to my office and pounded out some work until about noon. I went into my room and dropped my clothes off onto the bed. I grabbed a towel and headed out to the backyard. The sun was shining directly overhead. I lay the towel over the chair and sat down in the lounge chair. After a half hour I was sweaty and hot. I got up and dove into the pool. The heat from my body made the water feel cool. I did a couple of relaxed laps before I got out and lay on my stomach to tan the other side.

I heard the sliding door to the house open. I opened my eyes to see Chris coming out naked. He came up next to me and slid one of the other lounge chairs closer to mine. "Afternoon James, I was hoping that you would still be out here catching some sun."

Chris dove into the pool, slicing into the water with the grace of a dolphin, the top of the water hardly rippled. I got up and followed him with the grace of an elephant sloshing the water in the pool from one side to the next. We both came up on the other side of the pool and sat on the shallow end of the steps. Just two naked guys sitting in shoulder deep water chit chatting. We have grown way too comfortable in such a short amount of time.

Chris turned to me, "James, I don't know about you but I have been trying to get a grip on what happened yesterday." I opened my mouth to comfort him, or apologize, or I wasn't really sure what I was going to say but Chris held his hands up to stop me.

"Let me finish before I lose my nerve. I've never done ANYTHING like that before. Jess seems to have this hypnotic way about her. I love her and will, obviously, do anything for her. I just don't want there to be any weirdness between us. I'm still not sure how this will all change when Emily returns. I want to ask Jess to move in with me so we can start our life together, but at the same time I really liked what we did together. I liked it a lot, more than I thought possible. I guess what I'm trying to say is can we still be 'close' friends going forward?" I swear Chris said all of this without taking a breath.

I looked down and could see that Chris had a major boner, "Look Chris I know exactly what you are feeling. At least you will have other opportunities with Jess to expand your desires, whereas mine may end completely when Emily returns tomorrow. Jessica opened up my eyes and my mind. She makes it sound a little more analytical than it really is. There are some emotional feelings behind some of my actions, for example I don't know if I could do what I did with just anyone either. I think that because it was you, that is what allowed me to go that extra bit."

I thought Chris was standing up to leave, that the conversation was getting too deep for him, "I know James. Seeing YOU dressed up helped me make my decision to dress as well. Knowing that it was your cock made me feel like it was ok to experiment and to go, for lack of a better expression, outside of the box." The tension lifted as we both laughed at his pun.

Chris walked over to the lounge chairs and lay on his stomach. I followed him, watching his tight ass muscles flex with every step. I sat next to him and he handed me some suntan lotion, "Would you mind James?"

I eagerly grabbed the bottle knowing that I would be touching his body, "No not at all."

I poured some lotion in my hand and started at the top of his back and worked my way down towards his tight ass. I squirted more lotion directly onto his back causing Chris to tense up, "Hey that's not nice." As we both laughed.

I started to rub the lotion in and as I worked further towards his ass. I assumed that Jessica did the same thing with Chris as she did with me, "So which size strapon do you like best?" I ran a well coated finger up and down the crack of Chris' ass.

Chris moaned his appreciation, "MMMMMM, that feels nice. She fucked you? That must have been hot. How did it feel? MMMMM."

I was visualizing Jessica pounding Chris' tight ass as I found my finger circling around his rosebud. Chris was not objecting and in fact was moaning. "Feels good huh? I love my ass played with like this, so it was the next step to see what something bigger would feel like. I never imagined how many nerve endings are inside. When that big cockhead pushed against my prostate I thought it was going to push my cum right out of me."

I continued to use the suntan lotion as a lube as I applied a little pressure to his puckered hole. Chris spread his legs allowing me a little more access. I could now feel each fold that formed around his puckered hole. His crack was hairless and so beautiful. My heart started to race. My cock was straining against my stomach as I leaned into Chris and massaged his ass cheeks. The tip of my finger centered on Chris' hole as I put the slightest pressure against his hole. I felt him open up to me. It was so exciting to feel this tight puckered hole allow me access.

Chris acknowledged his acceptance as he wiggled his ass and pushed back against my finger, "Mmmmm! Oh James that feels so good. I didn't know how sensitive that area is, please don't stop."

Chris pulled his legs forward tucking his knees under his stomach and offering his ass to me. His cheeks were now spread farther apart giving me better access for my finger and allowing me to watch as my finger continued to disappear into his soft, hot, tight, hole. I pulled my index finger out of his ass and quickly replaced it with my middle finger, which was longer and fatter.

As soon as my middle finger pressed into Chris boy pussy he pushed back against me and moaned, "OOHHHMMMMM!"

Chris dropped his head down onto the lounge chair and pointed his ass up as an offering, "Please James, please fuck me. I need to know what it feels like. Please it has to be you. I don't want my first time to be with just anybody, please I need to feel your cock inside and I know you will take it slow."

I threw my towel on the patio floor between our two chairs, grabbed Chris' hips and guided him down onto the floor. Chris assumed the same position and I used the lotion to put two fingers into him. I massaged the inside of his rectum. I felt around the soft spongy tissue inside. I took advantage to explore the inside of his body. I kept working my fingers into his ass until the tip of my middle finger felt the nub of his prostate.

"OH god yes. Oh shit that feels so good, don't stop." Chris moaned as I continued to massage his prostate and apply a little pressure.

I applied more lotion to his ass by placing the tip of the bottle to his ass and squirting it into his hole. Then I put more in my hand and rubbed it all over my cock which was now coated in a white film. I moved between his legs and lined up the head of my cock with his stretched hole.

As the tip of my cock touched Chris' hole, Chris pushed back while I simultaneously pushed forward. His hole was ten times tighter for my cock as it was for my finger but my cockhead started to stretch his opening. I rubbed Chris' back as I pulled back and pushed forward a little harder. I felt his hole give a little more each time I pressed in. I wanted this to be the best experience he could imagine. I wanted him to love it having a real cock fuck him.

My cockhead now went in almost all the way, but not past the sphincter muscle. I placed some more lotion on his ass and when I pushed forward Chris slammed back against me causing the head and the first couple of inches to disappear into his boy pussy.

Chris exhaled, "YES! Don't move, hold still and let me get used to it. The pain is so sharp but it is easing up just as fast. Oh man I could feel my ass stretched open."

I continued to rub his back and held myself real still. He slightly moved in and out, and wiggled around my cockhead trying to adjust. I knew the pain and enjoyment this brings as your body adjusts. Once the initial pain subsides the following is pure bliss. I leaned forward bringing my chest to rest on Chris' back, being sure not to dislodge myself from Chris' ass. I purred into Chris' ear "Is it everything you expected? Does it feel good to have a cock pressing into your tight pussy? Ya that's it baby shake that tight ass of yours and beg to be fucked like the little pussy boy you want to be."

Chris was almost in tears fighting back his pent up emotions as he pushed back against my cock and accepted nearly the full length, "UUHHHH! Yes James please fuck me. Fuck me please. Your cock feels so good. Stretch my pussy please. Fuck me long and hard."

I kissed his neck just below his ear so that he could feel and hear the tenderness of this emotion. I was grateful that he chose me to pop his cherry and I hope he does the same for me. I want to feel what a real cock feels like fucking me. I slowly rose back up to the kneeling position behind Chris. I grabbed onto Chris' hips for support and slowly pulled my cock out of his ass. It was so exhilarating to watch my cock coming out of his ass as his puckered hole clenched around my cock. The skin of his tight little hole was stretched open like a beautiful flower blossoming. It was pure poetry.

I pushed back forward very slow. I wanted to enjoy this just as much as Chris. My cock disappeared into Chris with little resistance now. His well-defined muscled body flexed as I continued to push my cock into his body becoming one with him.

Chris was begging me to fuck him now, "Please James harder. Fuck me harder. Faster fuck me faster. I want to feel your balls slap against me. I want to feel your cock deep inside. FUCK ME PLEASE."

I held onto Chris' hips almost digging my fingers into the fleshy part of his body between his hips and cock. I started a nice easy rhythm, at first bringing my cock almost all the way out and pushing back in, until my balls slapped against his dangling ball sack. Chris was moaning and grunting. His cock was swinging underneath him and a few drops of his precum flung beyond our bodies and landed onto the concrete patio. I was fucking the juice right out of him. That spurred me into a little frenzy and I started shorter more aggressive lunges into him.

My cockhead started to hit his prostate. "OH ya that's it James. Oh my god, yes that's it. You're going to make me cum, fuck me harder James please. Make me cum by fucking me. SSSHHHIITTTT YEESSS!"

I felt my cock head press against the hard nub of his prostate and I held still and ground my cock against it before I started my hard assault on his ass. "Is this what you like Chris, having a man shove his cock in your tight little pussy? Huh boy? Tell me you like cock? Tell me you want to be filled up with my cum and treated like a little cock slut! Ya that's it push back on my cock Chris, show me how much you want this cock buried inside your ass."

Chris was pounding back against me just as hard as I was shoving my cock into him. The sounds of our skin slapping against each other filled the backyard with the sounds of an audience of applause. It was too much for me to hold back any longer and Chris was there as well. I knew Chris couldn't stop his orgasm as his body froze and tensed up. My cock pushed his prostate button for the last time.

"AAAGGGHHHHHH!!!!! MMMMMMM" Chris screamed as his body trembled in my hands.

I held him tight as my own balls tighten up and I felt the surge of cum rush through my cock as it expanded his ass just a little more. I jerked my body a couple of times to let the cum flow into his ass. I wrapped my arms around his chest and rested by body on his back. Chris flexed his ass muscles a couple of times around my deflating cock until I felt it slip out of him. I pressed my softening cock back against his ass and let my cum drip out of his ass and down and onto my cock. Chris wiggled his ass against my cock thanking it for a job well done.

I kissed his back and sat back upright. Slapping Chris on the ass I stood up and dove into the pool. I came back up and propped my head on the edge of the pool facing Chris. Chris was on his back fingering his stretched hole and jacking his cock. His legs were up in the air and his cock was pointing to his face as he let loose another torrent of cum all over his face and chest.

I never witnessed another guy jacking off before and it was very erotic. It was so erotic that I felt my cock rise again. I hoisted myself out of the pool and walked between Chris' legs and grabbed his ankles. Without asking I just shoved my cock back into his cum dripping ass. I leaned into Chris and started to lick his cum from his cheek. Chris turned his head and drew me into a kiss. This is the first time that I made out with a guy, just between us guys. It felt different. There was an emotional connection.

I fucked Chris like a lover this time. I watched his eyes glaze as my cock fucked him. He was enjoying the pleasure of being fucked. The elation in his eyes as all of his inhibitions released as he enjoyed being ravished. I kissed him deep and hard. We didn't cum again, this was about bonding emotionally. We both got up and went into the pool.

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