Eli discovers his Bi side

My given name is Elijah, but everyone calls me Eli. I'm a fit Mexican male in Southern California. Life here is what you make of it. In my early to mid 20's, life is as fun as I make it. All through school and college it was women I chased and when I got lucky, nailed. I love the female form. Their bodies; tall/short, thin/thick, hourglass or a pear...all do the trick for me. Asian, Latina, Black, Middle Eastern are all attractive to me. So I was shocked when I accidentally had sex with a man.

It was a late Thursday night, after work, and I was driving home. The streets were dark and there was little to no traffic. I was pulling up to a red light, and saw a car waiting in the left turn lane. As I came to a stop, I looked over and saw a 'woman' in a red dress, and long white gloves holding the steering wheel. I say 'woman' but they were clearly crossdressing. I took the chance as she looked over, and gave her the international hand sign for a blow job. My fist pumped in front of my mouth, while my tongue poked the inside of the cheek creating a swell. She nodded 'yes' just as the light turned green.

I followed her as she drove to the left and pulled over in a side street. Parking my car behind hers, I got out and approached her. The outfit was very convincincing. She was sleek & slim. The dress was a red satin or silk, and the white gloves that came up to her elbows gave her that classic Hollywood vibe. The long flowing black hair had to be a wig, but it all worked.

"Hello" she said in a slightly raspy voice "how are you?"

"Better now" I replied "You. Look. Beautiful!" I praised her

She put her hand on my chest and ran it down to my abs, then belt buckle. My hand fell on her waist/hips and pulled her in. I started kissing her neck down to her collarbone. Her hand started to undo my belt buckle and zipper. Her hand found my stiffening cock monster, and she started squeezing it.

"Mmm! You're big... and thick" she smiled.

"Only the best for you baby!" I said, sounding corny.

We stepped apart and she took my hand. She led me to her car, and I locked my car with my remote. When I sat on the passenger side, she immediately put her hand on me cock. I opened up my pants and dropped them so she could have full access. She took her gloves off before she drove away, allowing her to feel me skin to skin. Just a block or two away from where we initially parked, she pulled up to a driveway of a house.

"Are we going inside then? I queried

"I can't...rules are rules" she replied.

Her head dropped towards my lap, and I shifted the seat to drop so I could lay down more. Soon, I could feel her breath on my nether region. Her lips were placing dainty kisses around my shaft, teasing me further. My dick was fully erect and my foreskin was taut. Her hand was now squeezing my stick and then her lips touched the head of my cock. She started mouthing my manhood, lips and tongue working together to give me a sublime experience. My tummy was twitching with excitement, responding to the very well practiced fellatio. She really knew what she was doing! While she was face fucking my piece, I started to fondling her. I rubbed my hands over her prepubescent sized breasts, squeezing her nipples. My other hand massaged the back of her neck. I took my left hand and hiked up her dress and started squeezing her tight little ass. Parting her cheeks, I started running my fingers over her bumhole. This didn't last long before I put several fingers in my mouth and coated them in saliva. My left hand again explored her butt, opening her cheeks and starting to insert my fingers, just one at first, then a second. My middle and ring finger entered one knuckle, then a second knuckle deeper.

That's when she slowed down and came up to kiss me...I hesitated. Thoughts raced through my mind. I was okay with getting sucked off, but was I ready to get intimate with a man in a dress? After a pause, I looked her in the eyes...then took her to me and kissed her deeply. My tongue forked in & out of her mouth. I tasted just a hint of dick...and it excited me.

"I want to sit on you" she gasped.

"Then let's move to the back" I suggested.

We climbed out and pushed the front seats up and tilted them down. We climbed in from opposite sides, and I planted myself in the middle. She pulled out some condoms and started to slide them over my thickness...but struggled. Long before, I had learned that condoms also came in 'large'. She had regular size. Taking the condom from her hand, I put it on. She then produced a 2nd condom, this one with ridges. Understanding immediately, she wanted protection in case one of them ripped. Facing me, she straddled my lap, taking my monster cock in her hand and placing it where her anal pleasure pocket began. Slowly sitting on it, putting the tip right on her entrance, she put more pressure till it started slipping in. Soft and slow, she started with the head, then a little more. She pulled up, bringing the ring of the helmet closer to the sphincter... a moan escaped. She started down again going slightly deeper, then starting up again reaching the same point where the tip was just inside the pucker. Then down, this time a little more confidently. Now she was actually bouncing on my Big Johnson. She was fucking me like she had never been fucked before.

The more I thought about it, the more I realized it was tighter than any pussy I had fucked before. Worried I might cum too soon, I took the opportunity to run my hands over her upper torso. I shifted her back so my hands massaged her tiny breasts (wondering if she had taken hormone treatment). My lips started kissing her nipples, gently at first as she continued riding my stick shift. Reaching behind her, I placed both my arms behind her so my forearms were laying on her shoulder blades. This allowed me to cup her shoulders from behind. Now I had the leverage to start fucking her back and dragging her down hard on my oaken stiff member. Her moaning was rising to ecstatic cries of pleasure from the rough fucking I was giving her.

"Fuck me harder papi" she mouthed breathlessly.

Of course I obliged, pounding myself into her. She crested back, arching her back away from me even further. I lost his handle on her back, my hands immediately reached for her pubescent breasts and started twisting her nipples. She exploded cum onto Eli's stomach and moaned her approval. More and more I was getting so close to cumming but I didn't have quite the right angle. I pulled her forward, again placing my arms behind her and once again cupping her shoulders to really ram her down. A few minutes later, I was arching my back as my big thick cock exploded long ropes into the condoms.

The car windows were steamed up. The only sound was both of our ragged breathing and panting.

She looked at me, her eyes bemused with the pleasure she had just experienced. She reached down and wiped her cum off my stomach, and licked her cum covered fingers. So I reached up and started kissing her, tasting what remained of her sticky cum. We sat there kissing deeply, tongues wrestling like someone had declared a 'thumb war'.

"Oh. My. Gawd! Thatwasincredible" I mouthed breathlessly into her lips.

She smiled..."Wait till next time papi"!

In the days that followed, I secretly started watching gay porn. I was transfixed with the six pack muscle bound gay men, but more and more I was pulled to the sissy porn. It started giving me ideas.

It wasn't long before I started texting her dick pics. She responded with ass shots, and pictures of her lips with milk leaking out. She wanted me to think of her cum filled mouth, and I admit it was very enticing. Sadly, we had not been able to 'hook up' again. When we did, it had to be a quickie for lack of time and differing schedules. She loved to blow my veined rod, and I loved cumming in her mouth. Several times, we literally met in some parking lot or behind a building where she sucked me to completion. She had also started rimming me, which just blew my mind. I had never thought of my ass as a sexual organ, but it felt divine.

Since a holiday weekend was coming up, I started planning. I texted her to make sure she kept that weekend free. I had discovered a local coastal town was having a musical festival, and it had the reputation of being very gay friendly as well as hedonistic. In planning for it, I told her I would be taking her somewhere, and she should plan for nights out as well as for 'fun & games'. She begged me via text to come fuck her again, but I reminded her we would have a three day weekend together. I also said I wanted to save up my spunk for her slut mouth and precious bottom. Going farther, I sent her some pics I had lifted from a porn site of a few sissies, in full sissy attire. She texted back with shocked emojis and hearts. The weekend was here, and as planned, I picked her up from the house she had originally sucked me off.

She wasn't in her dress, no cross dressing today. He was dressed semi-casual but also stylish. Cream colored slacks with short sleeved button down and 'Cuban Pete" fedora. As we started driving out of town, his hand stayed on my bulge, gently squeezing it from time to time. Instead of hitting the freeway, I drove us to a head shop that had a lingerie section in the back. Leading him in without hesitation, I showed him an outfit I was going to buy.

His jaw dropped.

"No! Really?" he exclaimed.

"Not for you?" I asked, mildly surprised.

"Oh gawd no! I love it! I can't wait to wear it for you!" he panted.

With that, we had everything we needed. We drove with the windows down, enjoying the warm air. As we approached the coastal freeway, we could smell and almost taste the salt in the sea air. The breeze took on a quality that reminds people they can relax, they were near the ocean. It wasn't long before they pulled up to a hotel. It was a 60's era building, but since it was a beach town, it was well maintained and 'chic' in its own way. Quickly unloading their luggage, they got checked in and went to their room. I jumped in the bathroom to relieve myself, and when I came out I saw a sight to behold.

She was in thigh high fishnet stockings, capped off with 'come fuck me' high heels. She had the thinnest silk thong on, and her ass was up in the air. She had taken the liberty of arranging the pillows to support herself, and she was face down. Her impeccable wig in place. She had a bralette on that matched her silk panties. I knew what she wanted. Her asshole had a ring of lipstick making her pink starfish so beautiful. I dropped my pants, and intended to fuck her good, but then I had an idea.

I got a bottle of lube out, and squirted some on her upturned ass. I started massaging her cheeks, and spreading them apart. I used my thumb to tease her hole. She started moaning, encouraging me. That's when I gave her a good spank on her tush.

"Ah!"

I went back to massaging her rear, and used my thumbs even more to tickle her fancy. Squirting more lube on her, my massages became harder, kneading her like a hardening bread. Raising my hand, I spanked her harder.

"OH!"

"Do you want more?' I teased.

"I want you to fuck me, but don't stop" she relented.

I swiftly gave her three hard spanks, my hands clapping loudly against her flesh.

"Oohhh" she groaned.

I dropped to my knees and started licking that lipstick on her hole. She was shocked to say the least. She pushed back, her tushy being shoved towards my waiting mouth. My hands opened her cheeks as much as possible and I ate her as I would devour pussy. My tongue would dip down and lick her taint, just shy of reaching her balls.

"Thought I was going to dick you down, didn't you" I teased.

"Yes, that's what I want," she gasped.

"And now?' I asked with an evil grin.

"Do what you want Daddy" she whispered.

I stood, lubing my throbbing shaft as I used my fingers to open her up. Again she pushed back, inviting them deeper. I pushed two fingers in, then tried for three. She loved it. I placed the tip my dick on her ass, and shoved it in hard.

"Oh FUCK" she almost screamed.

I grabbed her hips and started fucking her like a dog. Jamming my thickness into her, mercilessly. She was crying out in painful ecstasy. She reached back with one arm, which I grabbed by the wrist. She immediately brought her other arm back. I now had her by both wrists and used the leverage to fuck her with a hard rhythm. She was crying out, and made me fuck her harder. I didn't know it at the time, but tears were welling up in her eyes. Even if I had known, it only would have made me hornier and fucked her harder. She twisted her wrists away from me, giving me more leverage. I used it and started banging her bussy with reckless abandon. The clapping sound of my pelvic area striking her cheeks was intoxicating. I felt her body spasm...I was sure she had cum. I was near climaxing myself.

"Did you like that?"

"More...please..." she begged.

I finished with a fast paced thrusting that had her sobbing. When my shot leaped from my cock, she started moaning a long low guttural row. I gave her a few more thrusts before collapsing next to her on the bed.

"Make me feel beautiful," I said.

Her body, still in shock, winced over as she started kissing my body. Small little pecks across my chest, then abs. Her hands ran over my body with a silky smoothness. Her lips found my erect nipples and she started sucking them. She continued for a good while, while I dozed off in a euphoric stupor.

Later that evening, we showered together. When I say 'showered', I mean we groped each other in the steamy hot water. The soap was an invitation to rub our hands all over each other. We kissed, we licked each others lips and tongued each other. We stopped from fucking again, simply because we both wanted to wait and have our fun at night.

We had a quick dinner in a cafe just a short walk down from our hotel. A lot of people, like us, were in from out of town for the festival. The energy was eclectic, as so many young good looking men and women of various ethnicities and backgrounds came together to revel in our youth. After dining, we returned to the room to get dressed for the event. I decided to wear jeans with a pair of vans and silk T-shirt emblazoned with a psychedelic print. She came out of the bathroom, her makeup and attire matched. She was in Britney Spears' school girl outfit. The shortest of plaid mini-skirts and the tiniest of white button down shirt tied up like a bikini top. Her thigh high white stocking in a pair of Mary Jane shoes. Her wig was tied up in ponytails. Last, she had her collar around her neck that read "slave" on the front. She handed me the collar as she walked to me. Her eyes stared at me with intensity.

"I've never done anything like this before. And never in public! I'm so excited".

We hopped on a shuttle to the festival, it took place on a bluff overlooking the Pacific Ocean. If I thought we would stick out like a sore thumb, I was deeply mistaken. Many young men were in drag and leather bondage straps. Most of the lesbians were dressed in scanty rave attire, thongs leaving entire ass cheeks out and barely covering there pubes. Breasts were out for the world except for the tassels and stickers over their nipples. Any number of them also sported leases. Sex was in the air and everyone felt it's energy. As we approached the venue, the loud music was pumping and almost everyone danced/walked their way in.

It might have been a musical festival, but it felt more like a bacchanal. The music was the background for the sexual tensions being released so widely and abundantly. Gay & lesbian couples everywhere were dancing and grinding against each other. Straight couple tourists equally enjoyed the orgy of fleshen desire. Occasionally, people could be seen trying to be discreet in a handjob they gave their partner. Others were in groups of three or more giving their attention to one lucky person in the middle. Amidst all of this I walked my 'slave' around enjoying the sights.

"Is she really your slave?" asked a dark skinned young man.

He was dressed in the smallest of Speedos, and combat boots. His nipples were covered in a bandaid X that had 'fuck me' written on them. His wanton desire was obvious due to the packed nature of his codpiece. My sissy slave looked at me with lust filled eyes.

"Suck him slave" I ordered.

She dropped to her knees, and started kissing his thighs while her hand cupped his meat and massaged it. I watched, my own cock stiffening as the dark skinned youth smiled and grinned at me. She had moved his thong/cup aside and a large stiff dick stood up, free and breathing the sea air. She gulped it down and was taking as much of it in as she could. Others were watching with huge smiles on their faces, one of which I realized was twisting their nipples.

"I'm Danny," he said, shaking my hand.

"Hey, Eli" I responded. All the while she was sucking his dong.

The slurping sound could barely be heard over the music. We both watched as she worshiped his dark phallus. Tired of watching, I leaned over and started kissing Danny, my hand tweaking his nipple. I felt her hand on my bulge, massaging then looking to open my pants. Instead, I moved behind Danny and pressed my bulge against his cheeks, our faces twisted so we could keep kissing each other. My hands caressed his chiseled chest even as my slave did her duty to his mountainous meat.

"Mmmm" Danny moaned. He was going to pop soon.

"You gotta come back with us tonight" I said.

"Then I should go find my beau," Danny informed me.

I tugged on my slaves leash, letting her know to stop. I assured her we would have more fun. The three of us walked around, Danny leading the way. Eventually we came to a knot of people clustered around a gay cowboy. He was wearing leather chaps and cowboy boots. There was nothing under the chaps except for a fishnet thong. His trunk was highly visible as the thong might as well have been absent. He was rotating, dancing like he was bucking a bronco. The group of people around him cheered him on. He had a tiny vest and obligatory cowboy hat that was currently in his hand. He waved it around in his hand as he danced and hee-hawed his body. It was an impressive sight.

Danny caught his eye, and the cowboy finished his routine. He bowed for his audience and headed over to us. He immediately kissed Danny, then turned to look at us.

"This is Eli and his slave" Danny explained.

"We were just watching your dance. You're fucking hot!" I gasped.

"And don't I know it! He said, snapping his fingers in a Z.

Tom, the cowboy was his name and he was the most gorgeous man I had seen. In exploring gay porn, I had intially been amazed by the six pack, hard bodies and Tom was picture perfect example of a virile gay man. The sexual tension was immediate. We walked around as a group enjoying the show, drinking and taking turns dancing and groping each other. When the show started to wind down for the night, Danny informed Tom I had my slave suck him and Tom wouldn't believe how good she was. We all agreed to head back to their room, since it was larger than ours.

As we walked to the shuttle, I kept eyeing Tom, and caught him checking me out as well. It turned me on to think about it. So far, I had been in control, fucking my sissy slave and never blown a cock nor been fucked. Tom was tempting me to no end, as was Danny. I was imagining being in the middle of a Tom/Danny sandwich when the shuttle stopped at their hotel. We reached the top floor, and walked into their suite. Almost immediately we started pawing each other. Tom & Danny kissing and groping each other as I squeezed my sissy slaves ass as I kissed her nipples. We watched each other as we played with our mutual partners. The tension was growing, and I had to take things further.