Fun and Games Ch. 06

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it and it was fighting back. The act of standing up from a sitting position was enough to remind me of the nasty anal bashing I had taken of late. What began as dull discomfort had become a stinging, biting pain at my tender entrance. But deeper inside, especially where Ron had lodged his giant cock up my ass, it had compressed some unknown body parts and I felt lingering sensations of something weird. I had read about it enough to understand that this was somewhat normal when someone engages in a lot of anal sex, especially with a large penis, and after 2 days of abstinence my body was finally returning to normal.

In the days without male sex my thoughts had begun to turn to a wonderful fetish I've had for years and I wanted to share it with someone. After 5 days of much-needed recovery after my last encounter with Ron, I texted Tim and asked him to meet me for lunch. It was of course going to involve sex but I felt that this particular discussion warranted a face-to-face explanation that would allow me to read his reaction.

We ordered lunch and after the waiter walked away I explained why we were here.

"I have a fetish", I hesitated. "It might sound a little weird so just bear with me. I like to wear pantyhose under my clothes sometimes. They feel good and especially in the winter they keep me warmer when I work outdoors on cold days. But to be honest it's mainly because of how it makes my thing feel." I avoided using the word "penis"...after all we were in a fairly crowded restaurant.

I was waiting for a facial reaction from Tim but there was none so far.

"I was wondering if sometime we could work that into something fun. Like maybe some time I could come over and have them on already and we could, you know, with me wearing them", I trailed off almost inaudibly. Tim was now smirking and it was hard to get a read on what he was thinking. Was it time to be embarrassed or was it time to make arrangements for me to come over?! It wasn't possible to say at that point.

"Basically", I lowered my voice, "I have fantasized playing a submissive role while wearing them, so you can kind of figure out where I am going with this, not something I want to say out loud, right? Not here, anyway." I sort of looked at the ceiling, wondering if this was a bit of a mistake, revealing now a fantasy and a fetish to someone who I still did not know all that well. Strike that...I knew him well enough to suck his cock but this was by far the strangest friendship I'd ever had. The combination was still really weird as it settled into my head that I had openly admitted that I wanted to be dominated while wearing sexy pantyhose. The cat was out of the bag.

"Oh, I know exactly where this is going and where it is going to go!" he laughed. "Coincidences with us are becoming so common it's hard to imagine what's next! I had an experience, a few actually, with similar things so, yes, by all means, we can work it in. What time do you have to be back to work?"

"I could probably spend another 45 minutes away. I have a meeting at 1:30. We don't have enough time for that..."

"No, not that" he said, "but I have another idea. Let's get going."

We made our way out of the restaurant, which was in a plaza that had several shops all around it. Tim knew exactly where he was going and I followed him into a department store and to the woman's lingerie department. The precision with which he moved through the area suggested that this was not his first time buying pantyhose, which I ribbed him about.

"So are you a 3x girl?", I laughed.

"Fuck you, 3x, I'm a 2x queen size!" he shot back with a laugh. "Actually I don't do this often enough to know my size. I have to use these charts to figure it out every time."

"So you like wearing these, too?" I asked in a low voice.

"Yeah, it's actually perfect for wearing under a suit. Keeps your dick in nice and tight and they go perfectly with when you wear sheer suit pants. I got used to wearing pantyhose for that reason a long time ago. I don't wear suits every day but when I do I usually pick up a pair of these to wear. When I come home after wearing them, it's as if I've been edging myself all day long. I'm usually so excited I have to pop and I enjoyed doing that quite a bit. How did you get into it?"

"It started with a suggestion from another guy to wear them in the winter when you're outside. He was right; it makes a huge difference especially when it's windy. But I began to like the way they feel and every once in a while I pick up a pair and masturbate with them. I usually cut holes in the front and back so I can, you know, myself." I was barely speaking above a whisper and a few ladies walking by gave us quizzical looks, no doubt wondering what two guys were doing in the pantyhose section talking in low voices.

"Well, I'm getting these" Tim said. "Brown is my color" he said laughing, "and this is my size." He rubbed the material and said that it felt pretty good. I picked out my own size and we went to the register like a couple of high school kids buying rubbers. I paid for them since it was my crazy idea and we started out of the store.

Once we were out of earshot of anyone, I said very brashly, "I want to get fucked like a whore wearing these pantyhose, Tim. Can you handle that?"

"Only if you can promise to do the same to me", Tim said.

"Cut a hole in the ass", he ordered. "I'll use it to feed my thick cock up your ass. Now that you've had anal a few times you know what to expect."

"Fuck yes, I do", I hissed quietly. "I'm ready to get a full night of authentic ass pounding. When you come I want you to spray all over my sissy pantyhose, my ass and back. Then we can take a break and you can clean off your cock and then I'll suck you until you come in my mouth. You can feel free to try to force me to swallow since this is all about whoring around and pleasing your big cock."

"Definitely!", Tim said. "I'll fuck your tight ass while you wear your sissy hose. I'll come on them and wipe my cock on them and the next time you put them on you can tell me how much you loved getting drilled while you wear your pretty pantyhose and I fuck your tight asshole."

Tim loved the idea and surprised me by insisting that he go first! He had done something similar a few years ago with some panties and was eager to experience anal sex while wearing sexy nylon pantyhose.

"I can't wait to see your big dick trapped by those sexy stockings", I said. "I wish we had more time! I'd fuck you up the ass right now!"

"Let's plan it for tomorrow" he said. "My asshole still needs another day to recover and I have some stuff to do tonight anyway. Plus it will give us a full day to anticipate it."

***

Back at work, with my sexy new pantyhose in my pocket, I made my way to the men's room and slipped them on. I loved the cool, silky feeling as each leg was covered with the sheer material. I put my underwear in my pocket and walked nonchalantly back to my office. The fabric of my pants rubbing against my legs felt so good, and my penis was super-sensitized by the nylon. After 10 or 15 minutes my testicles, pinned down by the stretchy panty, were electrified and just walking around made my cock rock hard, but the pantyhose hid my secret by reigning in my thick tool tightly against my body.

Wearing my own silky pantyhose I felt so feminine and sexy, and it was even more exciting to walk around the office wearing them without anyone's knowledge. I loved my rather innocent little secret.

"I love embracing this side of my personality, a sensual, feminine side where things feel nice and look nice", I thought. Anyone that knows me knows that is so not my normal personality! I am not a metrosexual by any stretch; I work construction so I'm frequently in jeans and dirty clothes at work and when I'm home it's more of the same. Any of the guys or women that know me would be shocked if they knew I liked to wear pantyhose and fuck myself silly with slippery dildos, but that's exactly what I love to do in my spare time. And now I could add "sucking cock and getting drilled by huge dicks" to the list of experiences that I enjoy.

To prepare for our pantyhose party, I cut a hole in the front so I could fuck Tim's ass without taking off my pantyhose. Likewise, when the time came to give up my own cherry red asshole to Tim, I was ready by having a perfectly round hole cut for his big dick. When I got home I took off my pants and looked at myself in the mirror with my sissy hose on. I was hard, my penis straining against the nylon and spandex. My balls had been trapped in the waist panty all day and were charged with sensitivity and damp with sweat.

As I watched myself in the mirror, I was trying to imagine which was going to be more fun: fucking Tim's tight ass while he slinks around in his sexy pantyhose, or having him pound me in my ass while I'm in my sheer hose. I began masturbating and decided that it wasn't all that important but it was sure going to be a fun comparison once the experiences were behind us. As I pictured both scenes I began to pop and shot a huge load of come right onto the leg of my pantyhose. I let it dry without wiping it up and read a book to fall asleep.

When I woke up I jacked off immediately, delivering a nice big slimy load of come onto my fresh fabric. I was going to work, so I decided stinking like a come shot at the office was probably not the best of ideas and I cleaned it up somewhat, although a semen stain was unmistakably visible.

In the morning I promised myself that I wasn't going to masturbate no matter how revved up I became. But promises are made to be broken and by 10:30 I was in the bathroom releasing a huge, hot load of cream.

When I got to Tim's house that evening both of us were so eager with excitement we could barely contain ourselves. He suggested in the interest of mutual pleasure we dildo fuck ourselves and come first. I made a counteroffer of having him lie face down on the floor and present his asshole to me through his pantyhose. Fortunately he was willing to negotiate and before long I was sliding my thick tool right past his pink ring and deep into his taut bung hole. He moaned like a whore as I began to slip my cock in and out of his tight little asshole.

"Yeah, you big fucking sissy", I said. "I'm wearing these pantyhose because I like to. You're wearing them because you like to get fucked in the ass like a sissy. Isn't that right you tight assed little sissy boy?"

"I LOVE getting fucked in the ass by your big hard cock!", Tim moaned. "I am such a sissy. Oh, fuck me like a sissy goddamit! Fuck my asshole like you want to! Fuck it hard and deep and fast motherfucker! Fuck me in the ass!"

I dragged my fingers over the sheer fabric covering his legs. It felt warm and smooth and so sexy. "Do you feel sexy?", I asked.

"Oh, yes, yes, I do!", he screamed. "I look so fucking good in my sexy pantyhose. I know I look good right now to you and you feel so fucking good up inside me. I hope you like looking at my sexy ass as you slide into my body! Feel me up and feel how sexy I am!", he said.

I grabbed at the flesh on his legs and buttocks as I slowed down a little and began a nice slow pumping of Tim's ass. "Oooh, yeah baby you look so good", I cooed. "You lookin' so good with me deep inside you. Oh, yeah, your body feels so good wrapped up in your sexy pantyhose." I became more excited and without warning I began to accelerate driving deep inside his body.

I slid my hand under his body and found his hard cock and traced the outline of it with my fingers. Tim screamed and began to orgasm wildly. I could feel the wetness of his semen trapped in the nylon as the less viscous fluids slowly began to drip from the surface of his pantyhose. My fingers fluttered over his hard penis trapped by the sheer fabric.

The anal assault I delivered to him in the following few minutes were unparalleled for me in my life. I have never fucked an individual, man or woman, with the brand of unadulterated, pleasure-seeking that he endured. I ran roughshod on his ass for as long as I could last, calling him sissy names repeatedly until my rubber stretched and snagged my semen load that poured into it. I had a tremendous payload of come that my body wanted to unload. Once the semen began to flow I practically blacked out, squeezing his stockinged ass hard as my glans super-pumped jets of hot come into my prophylactic.

"I feel like a bitch whore", he moaned as I screamed in ecstasy. "I'm such a dirty fucking whore", he trailed off as I wretched and spasmed inside his body.

My still stiff cock slid out of his tight asshole and he moaned as it popped past his ring.

"You are a fucking whore, no two ways about it", I said rather dispasstionately as I got up to get a drink of water. Tim was lying on his side covered in sweat, no doubt reeling from the pounding his ass had just taken, his dark brown pantyhose clinging to his body and covered in sweat, semen, and lube front and back. I laughed to myself as I looked at the hole in poor Timmy's stockings, vaguely recollecting ripping them wide open as I fucked him raw.

"I am a whore", he said, eyes closed. "I am such a whore. What can I say? I love to get fucked in the ass. I love a big cock in my ass and I'm not afraid to say it. It feels good getting stretched like a whore."

We both sat around and talked for a few minutes and then I made another suggestion.

"Tim, I'd love it if you could get hard go between my ass cheeks", I said. "I want to feel your cock against my skin with no rubber."

"You mean like a hot dog in the bun?", he asked.

"Exactly".

"Yeah, that would be cool. Let's do it."

I got onto all fours and Tim got behind me, slathering a huge amount of lube on my ass cheeks. In seconds his thick sausage was tucked inside my pantyhose and sliding against me, his cock trapped by my springy, sheer pantyhose, pulling it toward my body.

"Fucking awesome", he said softly. "Wow this feels fantastic. Your pantyhose are stretching to pull my dick against your ass cheeks and asshole. I can feel the heat of your asshole on my cock as I slide past it and it feels awesome!"

I reached back and with one hand pulled my ass cheek to the right, further exposing my most sensitive area. The lube and his thick, warm penis were exciting me so quickly I could hardly believe it. Even without penetrating me I was quickly approaching another orgasm. His thick bag of testicles slowly bumped against mine as he ground his thick rod against me again and again. With both contained by pantyhose, the sensations were electrifying because the nylon fabric scratched and stimulated each hair, each skin cell on both of our nut sacks.

"Oh, fuck that feels so fucking good!", I screamed. "Keep sliding your big dick on my ass! I fucking love it! I love you riding my ass with me wearing my sexy pantyhose! I am a fucking whore! Grind my ass!"

Within seconds I spewed another high-powered load of semen, although the evidence was hidden by the thick panty of my stockings. A wet spot appeared but in no way indicated what a raucous, intense orgasm had produced it.

Tim announced, "I'm ready to come!". I quickly slipped his cock out of my makeshift "pantyhose tent" or "bun slider" if you will, and rolled over onto my back, immediately jacking his big, slippery penis. To enhance his pleasure, I held my mouth open and stuck out my tongue, begging him to come in my mouth as I masturbated his huge penis. His ball sac was still snugly held in place by his dark brown pantyhose and I slid my hand up his thigh toward his balls and began to tickle them through the nylon fabric.

Each of his loud screams was punctuated with a watery jet of semen wetting my chest and stomach. I ran my fingers through his come with my left hand, rubbing it into my skin as he continued to ejaculate on me. As his orgasm waned, I wiped some of his slimy come onto my face, which caused him to hit yet another peak. He yelled even louder and as the last few pulses of spunk left his body I smeared the sticky fluid onto my face and hair, acting the full slut.

"That was amazing", Tim said, exhausted. "That was un-fucking-believable."

"I can't believe both of us had such intense orgasms without penetration. Very cool! I loved the come shot on my chest. I feel so...I don't know, feminine I guess. I like that feeling of getting come shot on me. It's really cool...so visceral and erotic."

"It definitely is a new direction for us. It's like...role play. It's a new way to see yourself and someone else."

"That's a good way to put it", I said. "I see myself as a submissive creature, my sexy feminine side. All men have it, just most are afraid to look at it in the mirror."

"Most are also afraid to have said feminite side fucked in the ass by another guy...wearing pantyhose, no less!" he laughed.

"You have a point!", I snickered. "This is so amusing and fun. I feel sorry for any man who has never stepped outside their heterosexual comfort zone and just..."

"Played?"

"Yeah! Played", I said smiling. "Just played around."

We took a few minutes to calm down and get cleaned up before I left.

"Before I go, Tim, I have a special request", I said.

"Name it."

"I would like to take my ass-fucking off-site. Can we combine fantasies?"

"Definitely!", Tim said.

"Well", I said, "I'd sort of like to..." I paused. "This is harder to say than it is to think about! I've fantasized about this for years!"

"Look at me, Jake. You just ass-fucked me while I wore pantyhose. I think we can share a secret! What is it?"

"OK", I laughed. "I want us to go out separately. I'll either be wearing these pantyhose under jeans or actually dressing up like a woman. I want to get picked up and fucked in an alley, preferably a dirty alley, standing up, while I hold onto a wall, or a dumpster. I want to get packed in the ass while standing up. A nice, filthy alley would be perfect, especially one where you can see people in the distance. The thought of being within earshot of a busy street is extremely exciting to me. Not so much to be discovered or even seen, just that it could happen."

Tim waited a few seconds.

"Well, it's certainly a specific request!", he said with a laugh.

"Yeah, it's a fantasy I've had for a long, long time. I had sometimes thought that was actually how I'd have my first experience, an unplanned outing that ends up in an alley. That obviously didn't happen! But I could still go for a deep ass drilling in that dark, dirty alley. It would be an added bonus if I got tag teamed against my will, as long as it was safe sex."

"I might need a little time to plan this", he said.

"Take as much time as you need. I've thought about this for years. Another week or two won't matter."