Question Answered

I began to dress for Mark, my lover who had a thing for mature crossdressers like me. I knew that like most men, that after removing my dress or skirt, he would be thrilled to see me in sexy black lingerie. Starting with my black satin corset waist cincher, and garter belt, I then sat down on the seat at the dressing table. Taking one of my stockings, I leaned forward and gently pulled it over my foot and up my smooth shaven leg. Repeating this with my other leg, I then attached the garters to the top of the stockings in the front and back. Every crossdresser learns at some point that for quick access to your panties, you have to put them on after your garters and stockings! Knowing that Mark would be fully turned on, I selected my black satin front panties with lacy trim and sheer stocking like back that showed my tight butt. Pulling them on, I felt my cock stirring again. What an evening it was going to be. Next, my favorite part of dressing to complete my lingerie. I selected my black satin 38 C bra with lace trim on the edges and lace back. Gently I slipped it over my shoulders and reaching my hands around back I deftly fastened it. Adjusting the front, I inserted my larger size silicone breast forms. Mark would be very pleased when he saw me like this, but he'd have to wait. He was going to see the totally feminine me fully first! I stood up to look for an outfit that would thrill him.

Looking in the mirror I recalled the time many years earlier that I was caught crossdressing by Greg, the husband of my ex wife's friend Ginny, wearing the exact same lingerie. They were staying at our house for a week while they were having some major remodeling done. Greg was a big strong guy, 6'2", maybe 200, a construction worker. His job site then was way down in the south suburbs, and he usually got back home around 6:30 or 7 pm. The girls were at work until at least 5:30 and I had the day off and the house to myself. Hmmm, day off, no one home, what do you think that a crossdresser is going to do? Yes, I went straight downstairs to the secret stash in the basement closet of course! Putting on my brunette wig then my sexy black satin lingerie and the highest heels that I had, I danced around the bathroom downstairs and got out my makeup. I love the whole process of getting ready then trying on outfits and snapping selfies. I had all the time in the world, and my makeup was on point. While I was applying the finishing touch, my lipstick, I saw Greg in the mirror watching me from the doorway. I turned around startled and ashamed that he now knew my secret!

"Greg! What are you doing home so early?"

"Whatever, dude!" He replied. "I never thought in a million years that I'd come back and find you dressed up like this! Tell me what's going on here?" He said sternly.

Not knowing what to say, I responded with "It's a hobby of mine since I was young, dressing up as a girl. No one knows about this and you can't tell anybody, ever! Why are you home now, what's going on?" My voice was shaking.

"There was an accident at work and a guy got hurt pretty bad. They sent us all home for the day while they investigated. I still can't believe that you're dressed up like that. It's so fucking weird seeing you like this. Are you some sort of faggot?"

Stung by this slur and embarrassed to be caught like this, I pleaded with Greg, "Please don't tell anyone about this, it has to be a secret! I'll do anything for you if you don't ever tell!" I was shaking.

"Anything?" he questioned. I could detect a slight change in his tone. "This is awfully hard for me to wrap my head around. I don't know how I'd explain this to anybody. My wife's friend's husband dressed up as a slutty whore!"

My head was spinning from this turn of events. A relaxing day of dressed up interrupted by a house guest who now knew my secret and was confronting me with it. "Greg, please!" I pleaded again. There was no way out of this except embarrassment and shame if this got back to my wife and family.

"Anything!" I said again.

"Anything? he asked. He looked me over and said nothing for what seemed like ten minutes but was probably only a minute.

"How about you be a slutty whore and suck my cock?" He said to break the silence. What other choice did I have? Of course I would suck his cock, but I didn't want to roll over too easily. In reality, it would be a pleasure to do so! I just had to pretend that he was in control and not appear too eager to comply with his request. My sexual adventures as a crossdresser and my gay explorations had given me a thirst for cock. But, he couldn't know this as it might be too gay for this normally straight guy.

Trying to sound scared and incredulous "Oh my god! Do, do you really want me to suck you off? I know that I said that I'd do anything for you, but I don't know if I can do that!" I replied.

Greg then reached into his pocket and pulled out his phone. "Well, let me snap a pic and send it Ginny!"

"Nooooo!" I screamed, now I was really scared about someone else finding out. "Please don't take a picture! We have to keep this a secret between us!"

"Then you'll just have to suck me off like I asked you to." Greg replied as he put his phone back into his pocket.

Feigning resignation, I said "Oh fuck, okay, I'll do it! Our secret, right?" I had no assurance that this encounter would ever stay a secret, but at least we'd both get a thrill from it.

"Now! I want you to take care of our little agreement!" Greg commanded me.

My heels clicking on the tile, I walked over to him and seductively spun around showing him my tight panty clad little ass. He reached out and grabbed me by my hips, fondling my ass and reaching around front and feeling for my growing hardness. I spun around again and rubbed my hand on his crotch. He was wearing loose athletic shorts and his hardness was quite apparent.

"So it seems that you do like what you see?" I asked.

"Get down on your knees and I'll let you know if I like it after you wrap your lips around my cock!" he again commanded me. It seemed like he hardly noticed my pretty makeup, my eyes and lips painted so feminine. He was focused only on the pleasure that I was about to give him. Getting down on my knees as he directed, I again rubbed his hardness through his shorts. I pulled down his shorts in one motion taking his underwear with them. "mmmmm" He moaned as I pressed my pretty face against his cock and balls, savoring his masculine scent. Amazed at how rock hard he was at this moment, I tenderly began bobbing my painted lips over his cock, pretending to be a novice. Again, he moaned with pleasure. What guy doesn't want his cock sucked on demand, by a woman or a pretty crossdresser? Continuing with my sucking, I wanted to control the action. I didn't want him go all out and face fuck me. The pleasure had to go both ways.

Pausing for a moment, I pulled off and looked up at him making eye contact as I stroked him. "How's that? Are you enjoying this?" Before he could respond, I wrapped my lips again around his cock, maintaining eye contact, and continued my up and down motion. I gently cupped his balls, then pushing his cock against his belly, I sucked on one and then the other. He was moaning with pleasure as I took him in my mouth again. Now, the only question was how fast I wanted him to cum. Maintaining eye contact always turns a guy on, and a little vocal encouragement will help things along too.

"Mmmm, mmmm. Your hard cock is soooooo tasty!" I said seductively, coming up for air. Then, jacking his cock while still looking up at him, I paused again briefly. Holding his cock with both hands I licked the mushroom tip all around. He was delirious with pleasure at this point and I knew that he had to be close. He was now my toy and plaything. Releasing my grip, and sliding my hands around to grip his butt cheeks, my mouth slipped down his hard cock as I throated him. I slowly pulled back up to the tip, licking it then sliding my mouth down slowly until my nose was nestled in his hairy bush. Moaning loudly he exclaimed "oh fuck yeah, suck me!" For several moments, I continued, pausing at the bottom, then attending to his cock head and sensitive underside.

Gay guys love to throat, but I'm sure that it's the rare married guy's wife who will freely throat her husband's cock. I was feeling very gay and free at this point. Beyond hard, I was super turned on too and a wet spot of pre cum had moistened the front my panties. Greg was getting the full loving attention of his manhood and didn't care who's mouth was wrapped around it.

No longer able to delay his pleasure, it happened. "Ohhhhh, fuuuck, yeaaah!" he yelled as I felt the first shot of his load shoot into my mouth. I locked my lips around his cock in a loving gay embrace. He shuddered and his legs were shaking as he pumped his load into my waiting mouth. His tasty semen coated my tongue as I attempted to handle it all, gripping his naked butt cheeks to maintain control. It was safe to say that we were both in heaven. His motion slowed as the last of his load emptied from his hardness. I kept my lips tight around his cock, savoring the taste, feel and enjoyment of the endorphin rush. When he was done giving me his load, his cock didn't soften, maintaining it's wonderful stiffness. That feeling of being so sexually charged that your cock stays hard even after you've cum.

He pushed me away, finally done, and leaned back against the wall and slid down to the floor, sitting. He exhaled "wow! That was incredible! Beats any half hearted blow job my wife ever gave me! You've done this before, haven't you?"

"A couple of times" I lied. "I try to copy some the more exciting scenes that I see on the porn videos." Half true, who doesn't get off on exciting blow job and cum shot on a porno?

I got up and walked back over to the mirror to check my makeup. Except my lipstick which had all rubbed off on his cock, I still looked and felt pretty. My cock was very hard and still tenting the front of my panties and I leaned over the counter to reapply my lipstick in the mirror. The terror of potential exposure as a crossdresser had turned into an interlude of pleasure. I had no idea that it was about to continue.

Greg then got up and walked over to me at the mirror. Grabbing me from behind, he turned me around and kissed me passionately.

"You're so fucking hot!" he exclaimed and kissed me again rubbing my hardness with his hand. Surprised as heck by this turn of events, I was used to guys zipping up and leaving in a hurry after they got what they needed. He then reached into my panties and fondled my hard cock as we kissed again. Wowie! This was turning out to a very interesting afternoon. What happened next blew my mind. Dropping to his knees, Greg licked the tip of my cock then opened his mouth and started sucking me! After the way that he confronted me, I couldn't believe in a million years that he'd return the favor! Had I unleashed a latent gayness hidden deep in his psyche, or was it the random opportunity that had presented itself, being free to explore another man ( who was presenting feminine ) in a sexual way without any constraints.

I wasn't sure if he'd ever tasted cock before, but It seemed like with his new found desire, he couldn't get enough. Pulling off me, he picked me up and carried me out of the bathroom to the couch in the basement. He set me down gently and then returned to sucking my cock. Totally blown away by this new twist, I was again in heaven. Straight guys never return the favor and Greg seemed very straight except that he was slowly and eagerly making love to my cock. Going with the flow, I just was going to let him play with me until he was satisfied. As he explored my cock with his mouth and tongue, he slowly moved down to give my smooth shaven balls some attention. Spreading my legs open wide, he fondled and licked my balls, then he plunged his face between my crack and started rimming me. So fucking enjoyable and so very gay! I just couldn't wrap my head around how passionate he'd become towards me. Who doesn't love being rimmed? In my twenties I discovered the pleasure of rimming this girl who was a FWB. My wife had enjoyed it earlier in our marriage, when I rimmed her but then stopped. Like many guys, I enjoy giving or receiving depending on the partners.

Greg returned his attention to my cock and began to finger fuck my lubricated hole. I moaned from the intense pleasure from and if he kept it up, I was going to shoot down his throat.

He was finger fucking me hard. "Ohhh, that feels so fucking good, Greg. You are going to make me cum!" I yelled out not sure if he was willing to take it in his mouth. Then as I came I called out "Oh Fuck yeah!" Pumping the first of three strong pulses into his eager mouth. Question answered.

I was on my back on the couch. He moved up from my crotch and kissed me strongly sharing my load between us. So hot and so gay, I loved it. As he pressed against me with his embrace I could feel his hard cock on my thigh.

"Mmmmm, that was lovely," I said tenderly to Greg. "You sure surprised me with that!"

"So fucking hot!" he responded "You've got me so charged up" as he kissed me again, grinding his hard cock into my groin. "I'm going to fuck you silly now!"

Random, unplanned sexual encounters turn out to be so intense and hot. Ours was just that, and it was about to take another turn. Most of my previous sexual encounters as a crossdresser, I was a dominant top and took the lead. Now, I was about to bottom for a highly charged formerly straight man who, it seemed, couldn't get enough of my feminine charms, lol!

"Let's go up to your bedroom" I whispered to Greg. Also, it would be a lot more enjoyable if we were lubed up and I could grab some from the upstairs bathroom before he fucked me. He got off me and I gently drew my hand across his hard cock. I was still in a state of disbelief on the way things had turned out since he confronted me. My panties were on the floor next to the couch and I bent over to pick them up brushing my face against his cock. Slipping my heels off, stood up and pulled on my panties then walked seductively towards the stairs. My black lace bra, satin corset, garters and stockings were what got Greg going in the first place, and I was going to insure his continued interest. He started following me as I ran up the stairs, getting a nice look at my tight little panty covered ass. Sprinting to the bathroom on the second floor, I quickly located the lubricant and slipped into the guest bedroom where Greg and Ginny were quartered.

He caught up quickly and was fully naked. An attractive man with broad shoulders, muscular arms, flat stomach and narrow waist, Greg had a swimmer's physique. The quick jaunt up the stairs had not dampened his enthusiasm for making love to me as he was still rock hard. Approaching him I again stroked his cock. He grabbed me and again kissed me passionately, letting me know that he was ready for more. I dropped to my knees and began sucking and licking the underside of his tasty cock. Grabbing the lubricant, I then lovingly spread it over his manhood, handed him the tube and turned around with my ass facing him. This was going to seal our pact of secrecy and I was ready for him. Greg placed one hand on my hip and pulled my panties down. With the other he spread a generous amount of lube on my crack and inserted his middle finger into my tight hole causing me to jump a little. I knew what was coming. I was standing and bent over placing my face on the bed and giving him a better access to my boi pussy. Then I felt him press his cock on the opening of my tight hole. Using a gentle pressure he gingerly began to slip his penis into me, working it in slowly. The first insertion and thrust is always painful and I moaned softly in both pain and pleasure. He was a big guy and his big cock was very snug, taking a little effort to put it in as I tried to relax. He was taking his time and for that, I was glad he didn't just ram it in me. What little pain and discomfort there was soon subsided. It felt so good having him inside of me and I again moaned in pleasure. Greg grabbed my hips with both hands and started his motion.

"Ohhh, baby! You're so tight, you feel sooooo good. You're my hottie little bitch!" he exclaimed as he continued his rhythm. We'd already been in heaven twice today and now we were soaring to a crescendo of sexual bliss.

"Oh, yessssss! Fuck me! Your hard cock feels sooooooo good inside me!" I replied as he continued to pump his cock into me. His cock slipped out and I used it as an opportunity to jump onto the bed and lay back, spreading my legs for him. Climbing up on the bed, Greg again pushed his cock into my waiting hole, this time with one push and he was inside me with just an initial burst of pain. Ohhh, it felt sooooo fucking good! I was enjoying this so much, I resolved to switch teams and be a bottom more often. My cock began coming to life again. What's wonderful about bottoming is the dual pleasure of being filled up and jacking your own hard cock.

I had been fucked before, but never like this. Surrendering with abandon receiving his manhood into me, I wanted only to submit to his thrusts and to give him pleasure. My warm hole felt his presence deep inside of me. Greg held himself up with his arms on the bed as he worked up a steady rhythm, fucking my willing ass with his horny cock. I was squirming and writhing in a cloud of sexual ecstasy. His orgasm was approaching as he fucked me harder and harder, faster and faster. As he began to cum he let out a low moan and fell into me, kissing me passionately. His climax was intense, using quick forceful thrusts as he deposited his cum deep inside of me. The fullness of his cock inside of me felt wonderful.

His humping slowed down as he lay on top of me, both of us breathing hard. He rolled off of me as his cock slid out of me. Both of us fully satiated, we silently contemplated our private sexual union. "So fucking hot!" he then exclaimed, "you are one heck of a lay!"

"You surprised me with your enthusiasm", I replied, "I thought for a moment that you were going to beat me up!"

"You looked so sexy in your lingerie, I had to find out if you would really blow me. My wife really isn't into sexy lingerie and you could give her some pointers on how to give a blow job" he told me. "I've never hooked up with another guy before today, but I've fantasized and always wondered what it'd be like. I might have gotten carried away ".

Greg's cum was dripping out of me slowly as the pillow talk with my new lover continued. "That was so hot, I loved every minute of it. Your cock is amazing. I still can't believe that you jumped me after I blew you. I bet that you are happy you got sent home today!"

Not wanting to have Greg get second thoughts about our encounter today, I excused myself saying that he probably wanted to clean up and that I had to clean up myself and get changed. I gathered my panties again and quietly went downstairs where it all started. Removing my lingerie and makeup, I took a long shower, masturbating while I relived our hook up. Thinking about Greg, I wondered if this was a one and done for him. Perhaps he'd feel guilty and remorseful about what we did. You never know.

After Greg and Ginny moved back to their house I again wondered about his interest in hooking up again. I wasn't going to push him.

Then I got a phone call from Greg asking me if I wanted to join him for the weekend to go fishing at their cabin on the lake in Wisconsin. Just the two of us.

Question answered!