This installment of the saga follows on from the episodes linked here:
Categories…. This story has anal, first time, blow jobs, gay male, lesbian, crossdressing, voyeurism, taboo.
Pick your poison.
Lucy had been masturbating while she watched Janie fuck my ass with the big strapon.
Now she suggested that since it had been me jerking off to Bruce’s cock that started all the activity off, we should invite Bruce to take part.
Janie didn’t know about the earlier Skype session and got pretty worked up as Lucy explained about it. Janie definitely wanted to see for herself how big Bruce’s cock was.
She seemed a little disappointed that Lucy had been fucking Bruce but it was quickly dawning on her that what she had going with my syster wasn’t exclusive.
Lucy also pointed out that she’d been pretty enthusiastic while she was pegging her bruther (me). Janie admitted that she was into it, and then added that she’d like to get fucked by a guy soon. It was months since she’d had a real cock inside her. I caressed her voluptuous body and told her I’d be happy to oblige whenever she wanted.
“How about right now, sweetie?”
“Oh god, yes!”
But Lucy nixed it.
“No, you two. I want to play with Bruce.”
So did Janie. And so did I, but I didn’t say so aloud.
I was so horny, wanting to fuck Janie, but the thought of Bruce’s big cock…
Lucy had an idea.
“Let’s play a game with him. We can let him pick who he gets to fuck then that person goes over to his house and the other two watch online.
“But let’s make it look like he gets a girl, no matter what.”
“How will we do that?” I asked. Lucy went to her dresser and picked out a pair of her panties.
“Put these on.”
“Yeah really, then we can line up in front of the cam, showing just from the waist to the knees and he’ll pick the one that he wants.”
Janie was into it and stood to pull up her panties.
Lucy did the same and I reluctantly slipped my syster’s underwear up my legs.
It felt very sexy, actually. The silky fabric running up my calves and then my thighs. I tucked my hardening penis into the panties and looked at myself in Lucy’s full-length mirror.
Turned around and looked over my shoulder at my ass. I looked hot. My petite little ass fitted Lucy’s panties perfectly.
I am naturally smooth skinned, so there was no manly hair on my legs that might give Bruce a hint.
Lucy’s ass looked very similar, of course.
Janie looked fantastic to my eyes. Big and bouncy, her ass barely covered by her skimpy drawers.
When she turned around and I saw how tightly she had pulled her panties up… the camel-toe… I became fully erect. Now the panties couldn’t contain my cock. Two or three inches were poking out above the top hem.
Lucy took hold of my meat and tried to tuck it between my thighs. This just made me harder.
There was no way I was going to lose my erection while Lucy was handling it. Or while I was wearing panties, for that matter. So we decided to line up and show Bruce our asses, instead.
We lined up and checked ourselves in the mirror. I stood between my Lucy and Janie. We were all three of us naked except for the tiny silken underwear. I was so turned on. I was going along with the plan because I was sure Bruce would pick someone else but I knew I’d be OK if he picked me.
Lucy had shown me how much I liked ass-play, and I’d cum while Janie had fucked me. Thoughts of perhaps having my anus stretched as Bruce slipped his cock into me filled my head.
We didn’t know how Bruce would react if he realized he’d picked a boy to fuck. Even though Lucy had been present when he and I had watched each other jerk off she didn’t know how far Bruce’s interest in guys went. So, maybe I’d get Bruce’s big cock in me. Or maybe he’d send me home.
I hoped that if I was picked, that the least we would do was some mutual masturbation and I’d get to grip Bruce’s monster. It was all good.
Or I’d get to fuck Janie while we watched Bruce doing Lucy.
If he picked Janie, I might get to fuck Lucy again, or maybe she’d do me in the ass again. I wasn’t so keen on Janie getting Bruce’s big cock because I thought it might spoil her for mine, later. But the odds were in my favor for a good outcome.
I needn’t have worried. Lucy started the online chat with Bruce, asked if he wanted to play – yes he did, obviously – and we lined up and let him see our asses.
Again, I stood in the middle. I couldn’t believe it when he said “Number two.”
Lucy asked if he was sure and he said that he was. So she told him that number two would be over to his house in a little while and broke the connection.
Lucy and Janie seemed disappointed and yet excited. I tried to look apprehensive and reluctant, but I wasn’t. I was going to get to see Bruce’s cock in the flesh and who knew what else.
Lucy had another idea. As he was expecting a girl, then I should go over dressed as a girl.
I’d never thought about dressing up in girl’s clothes before but the panties… how erotic it was. I agreed and the two girls started going through Lucy’s wardrobe to pick out an outfit for me. Since Lucy and I are both slim and about the same size there was plenty to choose from. Lucy has some very sexy clothes and soon they had an ensemble for me to put on.
Before she dressed me, Lucy said I should be smooth and sexy for Bruce and Janie giggled her agreement.
They marched me into the bathroom and Lucy turned on the shower. Then we all three stepped under it and the two girls started soaping up my entire body.
Lucy found her razor and began to shave all the pubic hair on my body. First around and above my cock and then my balls. She was very good and never nicked me once. My cock was rock hard with the attention it was getting and with my imagination of being with Bruce and being so close to the glistening naked flesh of my syster and her voluptuous friend.
When she had finished with my genitals Lucy made me lift my arms and she carefully shaved my armpits. My legs and arms have barely any hair on them and my chest has none so she pronounced herself satisfied and we got out and dried off.
First, they handed me a sports bra to wear. Lucy’s titties are sweet but not huge. The bra on me seemed to fit around my pecs perfectly. I felt myself hardening again as I looked at myself in the mirror.
Janie handed me a pair of knee-length white socks. Then came a micro skirt. And a satin slip. My slim runner’s legs looked long and lean. The skirt only just covered my ass. The shoulder pieces of the slip were mere string, so the straps of the sports bra showed. I looked very slutty.
I felt very slutty.
None of Lucy’s shoes would fit, so I wore a simple pair of gym shoes.
As I looked at myself in the mirror, I wondered… is this how girls feel when they wear clothes like this? Like they want cock?
Because that’s how I was feeling. I wanted cock. I’d never had cock before, but I wanted it now.
With shortish hair and no makeup, I looked like a boy in girl’s clothes, but a very femme boy.
Lucy thought about giving me some cologne to wear, but the soap they had washed me with was scented and feminine. I hoped it would appeal to Bruce. Oh man! I was hoping to appeal to Bruce. Like a girl on a first date!
Lucy had one more piece of preparation for me. She had me bend over and pulled down my panties.
Then she poured a ton of lube on her fingers and crammed it up my ass. Finally, she shoved a large butt-plug into me.
I stood back up and pulled up my panties. The plug was firmly in my butt. I loved how it felt. Lucy declared me ready. Asked Janie her opinion.
Janie took me in her arms. “He looks like you, Lucy” she said over my shoulder, and I felt her hand slip between my bare thighs and then up under my skirt where she cupped my freshly shaved balls through the panties I was wearing.
She whispered in my ear.
“So sexy. I like girls, but I like being fucked, too. When you get back, you can fuck me while you wear these clothes, if you like.”
My knees went weak as I stood there in her embrace.
“Oh yes, Janie. You’re my dream girl.”
“Sweet boy. Now off you go and enjoy whatever happens.”
Lucy drove me over to Bruce’s house and told me to start Skyping when we were ready. She and Janie would find something to do while they waited.
Bruce opened the door and looked surprised. I heard Lucy laugh as she drove away and then Bruce took my wrist and pulled me inside.
But Bruce wasn’t surprised about it being me, he was just surprised at me being dressed like a little slut.
“I knew it was you. I wanted you. I picked you.”
I was flattered. Didn’t know Bruce was interested and said so.
“Man, I’ve been checking you out in the changing rooms for a while. Your sexy little body turns me on.”
It excited me to hear him say that and I said so.
Bruce told me that he had never done anything with another boy. Watching me jerk off and having me watch him was the first time he’d done anything like that. But he’d been very excited, both by watching me stroke my cock and by knowing that I was watching him while I did it.
I told him I was the same, and I told him I was definitely interested in exploring more.
Then I asked, “Do you like what I’m wearing?”
“It’s the same outfit Lucy was wearing when I first fucked her. Did she suggest it?”
“Yes. So… I guess she is hinting something…”
Neither of us needed any encouragement, but Lucy didn’t know that.
“So, Bruce, we’re supposed to get online and let Lucy and her friend Janie watch while we do whatever it is we’re going to do”
“Are you OK with that?”
“I guess so. It’s kinda hot.”
We were still by his front door. The flat shoes I was wearing did nothing to change the big difference in our heights. I looked up at him, feeling feminine and submissive. He put his arms around me and drew me to him.
“You smell good.”
My knees weakened again, as they had when Janie held me the same way. I fell into him. Felt his hands slip down from my shoulders, down my back, and rest on my ass.
I looked up into Bruce’s eyes.
“Do you want to fuck me?”
As I said it, I reached between us and rubbed his cock through the front of his jeans.
His hands squeezed the cheeks of my ass through my skirt. It was then that he felt to end of the butt-plug I had embedded inside me.
“Oh you’re ready for me, I think.”
He lowered his mouth to my neck and nuzzled me there. Fondling my ass. His finger tips on the end of the buttplug were gently pressing it into me and then releasing it. Over and over. His hot breath was on my bare neck.
“Yes, I want to take you to bed, Abie.”
Suddenly all these words came tumbling out of my mouth.
“I want your cock Bruce. I want to touch it, feel it. I want to taste it. I want your cock in my mouth. In my ass. I want you to fuck me. I want to give myself to you. You can do whatever you want.”
He lifted his face from the corner of my neck and again I was able to look up into his eyes.
Then he brought his lips down onto mine and kissed me.
It was tender and earnest and my arms went around his neck. He bent down and his strong arms cradled me under my ass and he lifted. I spread my legs and wrapped them around his waist. Still kissing me, his hands back under my ass, he carried me through to his bedroom. Then he laid me gently down onto his bed.
He straightened up and I watched as he stripped off his clothes.
His cock was hard and huge. I wanted to touch it.
I sat up on the edge of the bed and Bruce moved to stand in front of me. It was a natural move to reach up and take him in my hand. Except my hand didn’t go all the way around, so I gripped him with both hands and started to stroke the length of his hard penis.
“Mmm that feels good.”
It did to me as well. He rested his hand on my head, tousling my hair as I pumped my hands along the length of his shaft. And then I felt a little pressure, just a hint, but it was all I needed, bringing my face closer to his cock.
I brushed the head of his penis with my lips. Started kissing his cock.
From the head and then holding it higher than his erection already made him, I leant down and kissed all the way down towards his balls. Then back up.
My kisses became sloppier and by the time I reached the helmet again I opened my lips as wide as I could and took as much of him as I could into my mouth.
His hands were both on my head now, holding me gently but firmly in place as he started to move his hips.
Fucking my mouth with that huge cock.
I was still able to grip the shaft with both hands, protecting myself from choking. My tongue explored the flange of his cock head and I tried different things. Sucking, licking, keeping my mouth wide, even a letting my teeth graze him slightly. His hands told me what he liked and what he didn’t. Before he came, Bruce pulled his cock out of my mouth and drew me to my feet. Holding me against him again.
“I want to fuck you, Abie. I think I’ve wanted to fuck you for a long time.”
“We should get online for Lucy to watch.”
“I suppose so, but it’s not how I imagined we might do it. I’ve jerked off thinking about your sweet little ass, Abie, and thought about fucking you. Making love to you.”
I’d never realized that Bruce had been having fantasies about me. I was so flattered. It made me want to let him do whatever he wanted. Even more. I was very aroused by his interest.
“Well,” I said, “perhaps we can do what you want first.”
“They’ll be impatient. And I don’t want to annoy Lucy. She has a weird hold over me.” Bruce admitted.
“I don’t care, Bruce. I want you to have me the way you want.”
“I never imagined you dressed like this, but I want you to keep the clothes on.”
“I like being dressed like this. It makes me want you to fuck me even more.”
He pushed me back gently and I laid back on the bed.
He reached up under my skirt and tugged down my panties. Then I spread my legs for him and he slowly extracted the butt plug. I wanted him inside me so badly then.
“Fuck me, Bruce. I want your cock so much.”
I looked up at him as he moved between my legs. Gripping his cock to aim it at my little asshole. I felt the head of his enormous cock touch me there and then some pressure as he started to push into me.
The lubed-up plug had done a good job of making me ready, and my desire for him to be inside helped, and I felt his slip his length into me in one smooth motion. I groaned in pleasure. Bruce did too.
“Oh Abie, I’ve wanted you for so long.”
I spread my legs wider below him and Bruce lay down onto me. He started moving his hips and his cock went in and out of my ass.
“I love your cock, Bruce. It’s so big. Stretching me. Making me feel good.”
He was making me feel very feminine and I liked it. Lying under him, in my slutty girl clothes, being penetrated by him.
I lost my erection while he was fucking me. But the sensations were fantastic and I was incredibly aroused.
His lips went to mine and he began kissing me while he fucked me. I put my arms around his neck and whimpered with the pleasure I was feeling.
Then I felt him tense up and he started thrusting harder into me and I knew he was close to cumming.
“Cum in my ass!” I clung tightly to him, encouraging him to finish off inside me.
He took his weight on one hand and slid the other one under my slip and he found the sports bra I was wearing. The final piece of female clothing for him to discover. He slid his hand under the bra and started rubbing my nipple. It was too much for him and he started to cum.
One last deep shove into my ass and then grinding himself against my cheeks as the cum spurted out of his cock and deep into my bottom. Finally he collapsed onto me. His hot breath on my ear.
I kept holding on tight, so happy that he had taken such pleasure from my body.
At last, he got up onto his knees and slowly pulled his cock out of my bum.
Bruce wanted to make me cum then and I wanted to cum myself but when he moved his hand up under my skirt and leant down as if to suck me off, I didn’t want it.
While I was dressed this way, I wanted to be very submissive. I didn’t know how to refuse him but instead suggested we take a quick shower before going online with the girls. He reluctantly agreed.
He went to turn on the water and I stripped off the girlie clothing I was wearing. I kicked off the little lace-up gym shoes, sat at the edge of the bed and rolled the knee-length socks down and tugged them off. Found the button at the waist of the micro skirt I was wearing and then the zipper and stood to let it fall to my ankles.
Except it didn’t fall. My erect ion had returned and the skirt was caught on it. Undressing from girl’s clothes is apparently as exciting to me as putting them on in the first place. I gave the skirt a tug and my cock sprang free. The skirt fell. Then I pulled off the slip. I caught sight of myself in the full-length mirror.
A petite guy with a big boner, no pubic hair and a bra. I stared for a few seconds. I was turning myself on. Then I took off the bra and went to join Bruce in the bathroom. My cock, sticking out in front of me, bouncing up and down as I walked.
Bruce was already in the shower and I opened the door and joined him under the warm spray. It was a natural thing to start soaping his body. He tenderly did the same to me, paying particular attention to my cock and ass. We were soon clean, stepped out of the shower together and started to towel each other off.
Now that I was out of the female attire, I felt more manly and while Bruce was drying my privates I let him stroke me and got up the nerve to indicate with my touch that I wanted him to suck my cock.
He didn’t need much of a hint. We went back to his room and he sat down on the floor with his back to the bed. He motioned for me to stand over him. I stood with my legs apart and bent over him, leaning on the bed. He took my cock in his hand and stroked it briefly before opening his mouth and letting me feed it to him. Our position let me fuck into his mouth as he sat there below me. I moved my hips back and forth. Feeling his moist lips run the length of my dick. Feeling his tongue brushing my cock head.
Bruce’s hands reached up and he gripped my ass, pulling me deeper into his mouth. He began deep-throating my cock. I stayed still and let him take my entire cock in. Felt his nose bury into the bare skin where my pubic hair had been before Lucy and Janie had shaved it.
It was an amazing feeling and I couldn’t stop myself. I move one hand to the back of Bruce’s head and I bucked my hips, trying to go even further down his throat. Moaning and telling him how good he was making me feel.
He sensed I was ready to blow and pulled away from my cock for just long enough to look up at me and say
“Cum in my mouth.”
His lips went back around my shaft and his hands were caressing my buttocks. I bucked my hips. He sucked my penis. His tongue was rough against the head. Lips clamped around the shaft. Sucking. And he made me cum. I shot into his mouth and he sucked it all down. Swallowed every drop of my sperm, I felt him sucking the last dribbles of cum out of my cock.
I pulled out and lay down on the bed. Bruce climbed up and lay next to me. Looking at me.
“I liked doing that. I liked how your cum tastes.”
“You were very good. I want to feel you cum in my mouth, now.”
“Later, maybe. And who knows what else? But we need to go online now or Lucy will be mad.”
So we logged in and connected with Lucy and Janie back at my house.
Janie was lying on her lovely stomach facing the cam. I could see past her shoulders and down the length of her curvy body to that spectacular ass. Lucy was behind her, wearing her strapon. The same one that Janie had fucked me with earlier.
Lucy told me to assume the same position. So I lay down facing the cam on our end. Now me and Janie were face to face. I could see in the corner of the screen what she and Lucy could see. I could see Bruce move between my legs, mirroring Lucy’s position.
“So Bruce, shall we fuck?”
“Abie, I want you to describe how it feels when Bruce fucks you.”
I wanted the girls to think this was the first time. I glanced over my shoulder…
“Take it slow, Bruce…”
“Don’t worry. I won’t hurt you.”
Lucy leant down and, although the view was obscured by her pretty face and flowing hair, I could tell by Janie’s expression that my syster’s strapon had penetrated her. Lucy lay atop of Janie and her face came close to the cam as well. She was slowly and gently fucking Janie while they intently watched Bruce and me.
I lifted my ass up a little. The girls could see what I was doing and both gave a sly grin. They knew I was into it. They could tell that I wanted to be fucked up the ass.
They didn’t know I’d already had the pleasure, but that was a secret for Bruce and me to enjoy.
“You want it, Abie, don’t you?” my syster asked. Teasing me.
I didn’t care. They both knew I like girls too. But since discovering the intense pleasure of having something enter my ass, I was like an addict.
“Yes Lucy. I’m ready for Bruce’s cock. I want it.”
Bruce leant down and placed his cock against my ass. Resting it in the crack. Then he started humping himself against my ass.
“Abie’s ass looks just like yours, Lucy.” he spoke over my shoulder into the cam.
“Will you pretend it’s me then?” she asked, “because you know I’m never going to let you ram that horse cock up MY ass, Bruce!”
I didn’t think Bruce would be imagining my syster while he was doing me for the second time. I knew I was enough of a turn-on for him. I reached behind me and touched Bruce’s thigh. Stroking his muscles there. And I lifted myself in time with his humping. Feeling his hard meat sliding along the crack of my ass, but wanting him to penetrate me again.
Lucy wanted a commentary, so I spoke up.
“Fuck me Bruce. I want your cock.”
He lifted himself and positioned his cock at my back door.
“Yes, like that. I can feel it pressing onto my tight little hole.”
The girls were watching intently. They couldn’t see Bruce’s cock enter me, but they could see his body moving over mine. They could tell when he pressed himself past my sphincter.
“Oh oh, he’s pushing into me.” I moaned.
“So big. Stretching my ass. It’s too big! So big!” Bruce kept up the pressure and the girls could see him lowering himself onto me and knew that his huge cock was going further into my ass.
“He’s going in deeper. Stretching me more and more.”
“Does it hurt?”
“No. No, I like it. The buttplug helped. It just feels so strange. So big in my ass.”
Bruce bottomed out in my ass. I felt his balls rubbing against my ass.”
“He’s all the way in. So deep in my ass.”
I was talking for the girl’s sake, and I should probably have been paying attention to Lucy fucking the gorgeous Janie on the screen in front of me, but what I did was flip the images so that Lucy and Janie were in a small corner of the screen and the image of Bruce fucking me was the whole rest of the monitor. I was able to watch as Bruce labored above me, driving his cock into my bottom and then pulling almost all the way out before repeating the action.
“His cock is like a piston! He’s fucking me so hard now.”
“Do him, Bruce!” Lucy called out.
“Fuck his sweet little ass!” Janie added
“It IS sweet. So sexy. I’m loving it!” Bruce panted as he continued fucking me. Picking up the pace.
In the corner of the screen I could see that Lucy was still humping her strapon into Janie as they watched, then I returned my attention to the main screen and watched myself getting fucked and fucked and fucked.
Bruce picked up his pace again and I could tell, from how he had tensed up earlier, that he was about to cum.
“Cum inside me, Bruce!” I told him, for the girl’s benefit and titillation.
“Don’t worry, no way I’m pulling out of your hot ass until I shoot!”
“Bruce I never imagined you’d get so hot for a little boy ass” Lucy said.
“Nor me, but it’s like I’m fucking yours” he told her, then whispered in my ear “but I like yours better, Abie.” I squirmed under him, trying to give him even more pleasure.
“Cum Bruce. I want to feel you spurt into my ass!”
Bruce grunted. Bucked his hips. Grunted again and then rammed himself as deep as he could go into me.
“He’s cumming!” I said to the camera. “Cumming in my ass. I love it!”
“Oh god. so big and fat and deep inside me. Cumming in me!”
Bruce slowed and then stopped his motion.
“Show us!” Lucy demanded.
Bruce pulled his long fat dick out of my ass and moved towards the camera. His cock glistened with cum and he showed the girls.
“Now you, Abie. Show us the cum dripping out of your ass.”
I turned around on the bed and got up onto all-fours. Reached behind me and flipped the hem of my skirt back up to uncover my bare ass and spread my legs so that they could clearly see my well-fucked hole and the cum that was dribbling out of it, and down over my smooth ballsack.
My limp dick dangled between my legs, but I could feel it hardening again now that Bruce was done fucking me. It lifted up. Bruce reached down between my legs and started stroking it.
“Don’t make him cum, Bruce!” Janie spoke up. “I want Abie’s cock when you get back here.”
Music to my ears. Now I turned around and watched as Lucy drove the dildo deeper into her friend’s cunt. My darling Janie, getting fucked on camera for my entertainment. I wanted to masturbate while I watched, but the promise of her big, bouncy, curvy body enveloping mine while her wet pussy enveloped my cock… I couldn’t take the chance of missing out on that.
“We should get back there quickly, I think.”
“I’ll be waiting, Abie baby. As long as your syster doesn’t fuck me to death before you get here.”
Lucy leered over Janie’s shoulder at the cam. At me. Look at me, she was saying. Look at me, fucking the girl you have the big crush on. I watched her pumping the strapon more and more forcfully into my darling Janie’s cunt.
“Well, we’ll hurry up and come on over,” I said, and closed the connection.