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It's been an interesting start to 2023. I've always identified as straight, but I think I have slid a little bit.
Maybe I'll start at the begining. The first week of January I was sitting in starbucks reading a book and enjoying the quiet time away from my crazy household. A tall blond woman walked in and ordered a drink. She looked familiar but I couldn't really place it. It nagged at me awhile but it quickly passed. Fast forward a week or so, and my crew is out for a few drinks (we work in heavy construction) it was Thursday, so I was drinking bourbon. One of my coworkers, Aaron, commented that it was funny a guy who drinks cappuccino would slug bourbon and soda at the bar, he figured I'd be drinking wine.
I don't think in the history of forever, I have gone for a coffee with any of my coworkers. I asked him how he knew I drank cappuccino. He told me he saw me in Starbucks last week. I didn't remember seeing him and apologized for not inviting him he said it was all good I looked pretty in to my book.
A few hours later, my alcohol addled brain put it together. I busted out my phone and sent him a text "blond, leather blanket and Lulu's"?
I don't think it was 20 minutes later my phone rang and he was in tears. He was terrified that I would tell the boys at work. He had nothing to worry about. I felt really bad. I tried, pretty successfully, to talk him down and once he did calm down I invited him back to that star bucks for a coffee. He accepted.
I arrived first, I ordered my drink and made my way to the comfy couch by the fireplace and waited. I didn't wait long, ten minutes or so Aaron walked in, still visibly shaken, he grabbed his drink and sat down across from me. Not feeling particularly patient at the moment. I addressed the elephant in the room. I told him he had nothing to worry about, what happens off the job is his business. He seemed to relax but still looked upset.
Now, at work most of the guys call me "dad" not because of my age, but because I tend to fret about my coworkers, and I often have some good dad advice or a shitty joke.
I told him he's going to have to tell ol' dad what's eating him. I don't like seeing him upset. He turned bright red and said it's pretty embarrassing he wasn't going to talk about it in public. I agreed and asked if he'd like to speak about it somewhere privately. He suggested his apartment which was only a couple blocks away. So we finished our drinks and took a walk.
Once the door of his apartment closed he collapsed into tears and immediately spilled his guts. He never felt quite right in his body and his "dressing up" helped him feel natural. I always suspected he wasn't interested in women, he was a bit distant when the typical construction worker conversations started, but it wasn't my business so I let it lay.
I'm a father of two girls, so I've survived my share of meltdowns, and I knew how to handle this (I thought) I picked him up off the floor and moved him over to the couch, sat down beside him, pulled his head into my chest and started stroking his hair. "it's okay sweetheart, now what should I call you"? I asked.
The transformation was instant, they recoiled a little before looking up at me, just like a scared little girl before whispering "Elle".
She physically relaxed at that moment. She was still sobbing, but had stopped trembling. I realized I had no idea what to do at this moment. I'm not nearly as smart as I think I am. So for a few awkward moments we just sat there.
Then my moment of brilliance struck. I patted her on the back. "Elle, I'm going to the kitchen to drink your beer, you are going to clean yourself up and introduce me to the real you"
This seemed to be the right thing and she sprung off. As I say in her kitchen drinking the absolute worst craft beer or the plant, I realized I had no idea what was going on or what I could actually do. I just knew my friend was hurting and I needed to do something. So naturally I drank, after the first one the next 3 didn't taste so bad.
I was just about to get up for beer number 5, that's how long she had been gone, when she finally showed up. She had done her make up, put on that blond wig I had seen before and painted herself into a very flattering blue knee length dress. With her figure and bone structure it was tough to realize what she was an hour before. She had put on a set of falsies, a tasteful c-cup and opted for a pair of matching pumps. At 10pm in any bar, she'd be beating them off with a stick.
She looked at me expectantly, I could see the terror in her eyes again. As I took in what stood in front of me I couldn't stop myself from smiling. Despite the look in her eyes she stood with a confidence I had never seen from them before. I didn't have the right words, so my half drunk mouth just led the charge "well sweetheart, sit down and tell me about yourself".
We sat in the kitchen for a couple hours while she told me all about Elle. We finished off the beer and started drinking a bottle of wine we found in a cupboard. At one point we moved to the living room because the kitchen chairs sucked.
Somewhere around midnight she stopped talking and just stared at me. In my state it took me a moment to realize this before I asked what was wrong.
She stood up from her chair and fell to her knees in front of me, I thought she was going to cry again. I didn't know if I could handle anymore tears.
Instead she surprised me and started running her hands up my thighs. What really surprised me was how my cock responded. It was instantly rock hard. I think she sensed this and moved her right hand to my growing bulge and started rubbing it more forcefully.
I admit I was confused, I knew who this person was, but all I saw was this sexy blond eagerly trying to play with my cock, I felt zero reason to stop her and a hundred reasons to let her do it.
Once she realized I wasn't going to stop her, she slid her hands up and started opening my belt, moving quickly to by jeans. She ripped my Levi's open with a pop, pop pop as the buttons opened. She slowly slid her hands to my back and ripped them out from under me, boxers and all.
I know I gasped a little. I couldn't believe how turned on I was. I could feel the precum leaking out the end of my dick.
She rocked back on her knees staring at my cock. She noticed the precum and leaned in and licked it off with the tip of her tongue. I let out a soft uncontrollable moan.
She stood up and leaned into me, "you've been so good to me it's my turn to be good to you" she whispered softly.
My cock jumped a little.
My cock isn't anything special, average girth, slightly above average length. It's pretty as far as penis's go but nothing to write home about. She stared at it as if it was made of solid gold.
She reached out and grasped my shafty gently, slowly working up and down, slipoing her hand under my sack and gripping them firmly. I gasped again. Elle just smiled and licked her lips.
As she leaned in towards me my cock twitched trying to jump in to her lips. She pressed her lips against my head forcing my cock through them, the sensation was amazing. As my head passed her teeth she drove her head forward until I felt myself in the back of her throat. Again, I couldn't suppress the moan.
She released my cock from her eager mouth and looked up at me, the terrified expression I saw rlearlier was replaced by a look of determination. She lifted my cock and ran her tongue along my balls and up the underside of my shaft. "I want this cock and I'm going to make sure you never want anyone else to have it"
She stood up and pulled me to my feet, I stopped to step out of my jeans, she dropped back to her knees. She knew what she wanted and decided not to wait. She took my full length into her mouth and gently slid up and down my full length. Her left hand slid up and down my thigh stopping to rub my balls occasionally.
One point when she grabbed my balls her fingers brushed close to my asshole, a gasped and my cock twitched in her mouth. She stopped what she was doing and released my cock letting it hang in front of her. She slid her fingers into her mouth working then in and out like she was just doing with my cock. She pulled them out with and loud pop and immediately took my cock back into her throat.
As I was distracted by her tight throat pulling on the head of my cock I felt her gently pressing her finger against my hole. Until this moment, no one has ever touched my ass, I didn't know what I was feeling, but I knew it was good. I was breathing heavier now, I could feel my heart pounding against my ribs like it was trying to escape.
Elle could feel my urgency. She pulled away from me and stood up, pressing her body against me. She leaned in close and wispered heavily into my ear "I'm going to give you the best orgasm you've ever had, but you are going to owe me, and I am going to collect"
I could feel her own cock, rock hard pressing against mine. It felt smaller than mine, but having it running against me felt good.
She pushed me towards the bed and I tripped and fell on my back. She walked around to the nightstand, this was the first time I noticed how great her ass looked. She reached into the drawer and produced a small bottle of lube, and proceeded to poor a good about on her hand.
While I was trying to figure out what she was doing she went back to work on my cock, gagging as my cock hit the back of her throat. I felt her finger back and my hole, slowly working it in. Without thinking a spread my legs wider to give her better access. She looked up from my cock and smiled. "I want all this cum you've been saving," as she licked my balls. She went back to my cock and very quickly buried it again deep in her throat, I was so distracted I didn't notice that at the same time she drove her while finger into my ass.
The sensation was amazing, I had no control over myself as her finger moved in my asshole I drove my hips up and lost complete control of my cock. As I came I could hear her gagging but she didn't let up, she kept sucking harder and harder as a squirmed to get away. She finally let me go and stood up, my cum had dropped down her chin and was now sliding down her dress. I was a mess, I don't think I had ever cum that hard. My legs were a little numb.
She rocked back and sat on her feet. She has made no effort to wipe the cum still dripping off her face. She smiled at me and asked if I mind. She laughed a little, it was probably the confused mook on my face. She slid her dress up past her waist, she was wearing matching lace panties, that was struggling to contain her. She slid them aside and out popped her own cock.
It wasn't a big dick, honestly it was only about half the size of mine. She wiped the cum of her chin and used it to lube herself up, working it up her little shaft, never breaking eye contact. I could feel myself getting hard again. She knew what she wanted.
She took her other hand and started working my shaft again until she was satisfied. As she stood up she laughed and said "I was going to wait to collect, but it looks like you're ready now" as she stepped forward I felt our bare cocks touch l, then I felt her wrap her hand around both of them squeezing them together.
"This is the first real cock I've ever seen, mine is just a clit compared to it." She gently punched me back, she adjusted her pillows so I was laying at and angle I could see her stroking our cocks together. "I want a real man's cock inside me, so bad it hurts"
She grabbed the bottle of lube beside us and emptied the entire thing into her hands. She applied a good amount to me, I could feel it dripping down my balls and across my own hole, she reached underneath and added a liberal amount to her own ass. I think she might have fingered her self a bit because she seemed to go cross eyed for a second. As she climbed on top of me, she pulled her skirt all the way up and out my dick between her ass cheeks.
"I've always wanted to be a cowgirl" she said as she lifted her self up and pressed my head against her right hole. I could feel it puckering against the head of my cock, like a hungry fish trying to feed. She lowered herself into my cock, her startled gasp turned into a long low moan of pleasure as she gradually slid my full cock into her.
Once all the way in she say there for a moment. " I've never felt so full, its like my ass was made for your cock"
"Pussy" I wispered. I realized how hoarse my voice was, I haven't said anything for quite some time. She seems surprised too. "Pussy" I repeated. "this is Ellie's pussy, and it belongs to me now"
What was I saying? I was balls deep in a guy wearing a dress. Or was I? As I looked at Elle, I only saw a woman, in her glory, slowly working my cock in and out of her tight hole.
"I'm going to claim your new pussy tonight, I'll be the first and you'll always know it" she looked at me confused. I just smiled. "I'm going to cum in you, that makes you mine"
She liked what she heard, her eyes closed and I could feel her clutch my cock inside her" I lifted my hips and heard her gasp.
She opened her eyes and stared into mine, she was intense. I smiled and grabbed her hips. "That's what you want isn't it? A hot load deep inside you"? I could feel her trembling, I looked down and saw that her clit was starting to leak. I gently rocked her hips back and forth until she picked up her own rhythm. She was moving faster now, her clit was getting noticeably harder. She reached down and stared stroking is as she rode my cock harder and faster I grabbed her hand and pulled it away. "No, you are going to cum like a lady or not at all"
That hit her just right. She let out another moan, more urgent this time.
" You want to cum for me don't you"?
"Yes" she wispered weakly.
" What did you say"?
"Yes daddy" she said more forcefully.
I wasn't expecting that, and I wasn't expecting how hot it sounded.
" Are you going to be a good girl for daddy and cum for me"?
She moaned again, I could see the veins on her clit bulging, she was all in now.
"If you cum for daddy, Daddy will cum in you"
The sound that came next was half moan and half scream.
"Don't you want my cum inside you?"
"Yes daddy"! I could feel her urgency. She reached between her legs again but I swatted her hand away.
"No, you cum like a lady"!
She fell forward, putting her hands on my shoulders, frantically working her hips. I leaned up and wispered in her ear. "If you cum like a good girl, daddy will cum deep inside that tight pussy of yours. You'll be daddy's little slut forever"
She let out a cry of absolute ecstasy. I felt her cum hit the side of my face. As she collapsed on me I rolled her over onto her back. Still buried inside her.
I slowly worked my hips watching her writhe as my head almost popped out.
"You made a mess"
"I'm sorry daddy" she wimpered.
I drove my cock back inside her, she squeeked
I slowly pulled my cock out of her, I leaned over her and rubbed my head in the puddle of cum she had left on her stomach. I stood up and stepped away from the bed "come here, I want your ass up in the air so we don't waste anything"
She crawled over to the end of the bed, her legs were shaking she was having a rough time. She stared at my cock, a mix of lube, sweat and both of our cum coating it. She wrapped her lips around it and took it right to the back of her throat.
I almost came again right there. That thing was just buried in her ass, covered in our cum and she didn't even hesitate. I pulled her off and slapped her ass.
"No, I want your pussy"
She turned around and spread her cheeks wide, giving me a full view of her tight hole. I pressed my head back against it only got her to push back hard taking half of it before I knew it.
I was committed. I started fucking her with long hard strokes. My dick was so hard I just had to cum, I didn't care about anything else. I was vaguely aware of our balls slapping together. I thought I felt her hand on her own unit. I was so absorbed in my own pleasure I almost missed her crying out, "oh daddy, oh God daddy, I'm going to cum again, can I please cum daddy"?
"Cum for me sweetheart, daddy will put this baby in you"
As she tightened up on my cock again I felt that familiar rush as I came inside her. She must have felt the cum because she let out a gasp while her little cock shot all over my right thigh.
I just stood there for a moment. Taking in what had just happened. I was straight when I got out of bed this morning, now I wasn't sure. What I did know is I just had two of the best orgasms of my life.
Elle was laying on the bed panting and glistening with sweat. Her wig was a tangled mess and at some point she had ripped her dress. I walked to the bathroom and began the process of cleaning up. I wiped the cum and lube off me, grabbed a fresh cloth for Elle and left to find my pants.
As I was getting dressed Elle came out into the living room. She has changed into a silky red baby doll with the matching panties. I really noticed how sleek and feminine her legs were. She walked up to me and wrapped her arms around me in a big hug.
"Thank you" she whispered. She then turned and went back to her room.
I let myself out and locked the door to make the drive home. Still not sure what I have done.
Monday at work, the boss notified us that Aaron had called in and quit. He decided the lifestyle wasn't for him.
It wasn't long until I heard from Elle again.
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