A blue-haired woman in her late fifties at least, was taking cock in all three holes while she was surrounded by at least six additional naked men with hard cocks: A sissy feels no shame for who she is or what she does, but only pride in her ability to bring joy to as many men as possible.
I had to admit that sometimes I still felt shame… for instance at this very moment, while I fucked myself with a dildo and imagined being used by as many men as possible… but that shame was always overridden by my lust for cock.
The video ended with Continued in Sissy Training 4, and then a URL with a command to take another test.
I snapped a picture of the URL, and then becoming very curious about something, I slipped the dildo out of my ass… having felt so full, and then suddenly so empty. I pulled on some sweats and went downstairs, and saw Mom and Dad watching the news. So I snuck into their bedroom and looked through Mom’s panties drawer.
My Mom was full of surprises!
Besides panties and pantyhose, a garter-belt and some stockings, were some thongs and, to my complete surprise, in addition to a vibrator… a strap-on harness and cock!
Why the fuck would she have a strap-on cock?
No way she used it on Dad!
Or did she?
On the other hand, no one would believe I sucked cock, wore panties and fucked myself with dildos either.
I borrowed a pair of her black pantyhose, and for some reason, just impulsively, some red nail polish, and crept back to my room.
I put the pantyhose on… which took ten minutes… since they certainly aren’t the same as socks… before I lay back on my bed and brushed my hands over my legs.
The nylons felt so soft and silky, and they made me feel sexy… sensual… feminine.
As I gazed at my feet, my impulsive nail polish grab now made sense… since my feet suddenly didn’t look right… and since I always wore socks to school, I could paint my toenails and no one would know.
So I slipped off the pantyhose and spent twenty minutes doing my nails… they say patience is a virtue, and I really challenged mine while I did my nails. Once I was done, which included a stealthy trip back to Mom’s room to snag some nail polish remover when I did a bad job at first, I let my toes dry and typed in the URL.
The website was called: How Big a Sissy are You?
It featured a collection of charts listing sissy things to do and how many points each item was worth if I’d done them.
Section 1: 1 Point Each
Used an anal plug
Dressed like a girl
Sucked a dildo
Worn heels of at least five inches
Worn panties
Had your nails done
Worn pantyhose
Gotten a pedicure and manicure
As I read through the first section (1 point each) I felt pretty good about myself, since out of a possible eight points, I only scored three, and ironically two of those points had occurred in the last fifteen minutes… since I’d just put pantyhose on and then taken them back off to do my nails. (Yes, I’d had them done for that charity event back in the day, but I was sure that wasn’t what was meant. The whole point of that exercise had been comedy, not sex.)
Either way, I typed in 3 for section one.
Section 1: 3/8
3 points
Section 2: 2 Points Each
Fucked your own ass
Sucked a cock
Came on your own face
Taken a facial
Swallowed a load
Worn thigh high stockings
Eaten your own cum
Worn lipstick
Worn a thong
Watched hypno sissy videos
Obeyed the instructions while watching hypno sissy videos
Watched gay porn
Oops! My masculinity took a hit in section two.
I’d been fucking my own ass almost constantly during the last two days.
I’d sucked many, many cocks… so many of them I’d totally lost track of how many I’d sucked and how many loads I’d swallowed.
I hadn’t ever come on my own face, although I imagined if I wasn’t caged, I likely could, if I tried aiming at my face. I could shoot pretty far. Over four feet… I’d measured… I know, weird… but I’m a guy.
I’d taken a few facials. One of them just yesterday.
Of course, I’d swallowed a lot of cum… a Super Big Gulp worth by now, I imagine.
I hadn’t worn thigh high stockings… even though I’d considered doing it just a little while ago.
I hadn’t ever eaten my entire load, but I’d eaten two of my own cream pies… one a few weeks ago from Rose’s pussy, and very recently from Camry’s butthole, so I guessed technically the answer was yes.
I hadn’t worn lipstick (except for that charity event, which I’d decided not to count) or a thong, although I did have a thong in my dresser… pink, of course.
By now I’d probably watched hours and hours of hypno sissy videos… which was a huge part of the reason for the predicament I was in… although predicament wasn’t really the right word, since that implied I regretted being where I was in my journey. And yes, I’d been parroting back all those ‘Repeat after me’ instructions since the very beginning.
And regretfully, after watching some hypno videos, I’d briefly perused the porn hub gay section, but hadn’t found them all that stimulating… although hearing masculine men whimper like bitches in heat had been kind of hot.
So sixteen points out of a possible twenty-four had me looking quite sissy-like.
Section 1: 3/8 affirmative responses (or guilty pleas?) for 3/8 points
Section 2: 8/12 affirmative responses for 16/24 points
19 points total
Since my nail polish was now dry, for some reason I felt compelled to maneuver the pantyhose back on. So I slid the sexy hosiery back up my legs, it going a little more smoothly the second time.
One they were back on, I confronted the three-point list.
Section 3: 3 Points Each
Deep throated a cock
Worn a cage
Gotten face fucked
Made a video while fucking yourself
Eaten a cream pie
Worn a garter-belt and stockings
Gone out in public wearing full make-up
Gotten pegged
Kissed a guy
Sucked a BBC
I scrolled down the list.
I quickly scored nine points by ticking off the very first three items on the checklist. Not only had I deep throated a fair number of cocks, several of them more than once, but I’d loved doing it! I was currently wearing a cage of course, and I’d been face-fucked numerous times by now, by now almost daily… and just like deep throating a cock… I loved it… loved the humiliation… loved the submission… loved being used like a slut.
The next item on the list was something I hadn’t ever done, and I never would. I couldn’t fathom ever making a video of fucking myself… what if it got into the wrong hands?
But as mentioned, I had eaten a couple of cream pies: one from Rose’s pussy and another from Camry’s ass. And I gladly would do so again.
I hadn’t worn a garter-belt and stockings… yet… but the idea of doing it was kind of appealing… they were very sexy.
I didn’t think I’d ever go out in public in full women’s regalia, and if I did, it wouldn’t be because I wanted to, but then again I wouldn’t put it past Rose to doll me up and take me someplace we wouldn’t be recognized. And if that’s what she wanted me to do, I’d do it. But for the purposes of this test, no I hadn’t.
Of course I’d been pegged by Rose and was hoping it would happen again… I would do anything for Rose.
I hadn’t ever kissed a guy, and although I loved sucking cock, I had no intention of ever kissing a guy… that was undeniably gay.
Lastly, I had… many times by now… sucked a BBC… I’d sprinted through three of them today alone.
So, I counted up the additional points I’d just accumulated. Six out of ten.
Eighteen points.
Not too bad.
Based on that section all by itself… I was 60% sissy.
Section 1: 3/8 (3 points)
Section 2: 8/12 (16 points) for a running total of 19/32 points
Section 3: 6/10 (18 points) for a total so far of 37/62
37 Points, or just a smidgen shy of 60%
Section 4: 4 Points Each
Taken a cum walk
Worn a vibrating butt plug in public
Served at a glory hole
Dressed in full girly attire
Eaten a cream pie of your own cum
Given car head.
A short list, and I’d only done two of the six.
I hadn’t ever taken a cum walk… and although I found the idea of a girl walking around in public with a load of cum on her face really hot, I couldn’t see a scenario where I’d ever do such a thing.
And until now, I hadn’t even known a vibrating butt plug was a thing… although I did wonder what it would feel like. Having a cock or a dildo in my ass felt pretty damn good, but what would it vibrating inside my ass feel like?
I had served at a few glory holes… and found it perhaps the most exhilarating of all my wild adventures… just cock after cock… although the BBC bathroom was also pretty wild.
Panties recently, and today adding pantyhose into my wardrobe, certainly wasn’t full girly attire since none of it would ever be visible on the outside, and I had no intention of ever going that far.
But then the only two cream pies I’d ever eaten had been filled with my own cum, and given all the cum I’d chugged down that wasn’t mine, I certainly wouldn’t hesitate to go there too.
Lastly, although I likely would enjoy doing it, I hadn’t given any car head. I’d gotten car head… three times, if I recalled correctly. Once at a wedding (or rather just outside in the parking lot), once after a football game, and once in my car when a MILF snuck outside for a load while her husband and kids were sleeping. Interestingly, the car had been parked all three times. But before you start giving me kudos for being a painstakingly safe driver, you need to know I wouldn’t hesitate to give or receive head in a moving vehicle, even if the recipient was driving.
Section 1: 3/8 (3 points)
Section 2: 8/12 (16 points) for a running total of 19/32
Section 3: 6/10 (18 points) for a running total of 37/62
Section 4: 2/6 (8 points) for a total so far of 45/84
45 Points, and down to less than 54%
As I advanced to the five-point section, I ran my hands up and down my legs… loving the feeling of nylon covering them.
Section 5: 5 Points Each
Got ass fucked
Had a sissy orgasm
Made a video while sucking cock
Got cream pied
Sucked a cock in public
Sucked a friend’s cock (as opposed to a stranger’s, or someone you only know because you’ve sucked his cock previously — N.B. a family member counts as a friend)
Sucked a cock while girlfriend watched
After feeling pretty good that my score had actually fallen after being just two for six in section four, I racked up some noticeable points in this next section.
The first two had both happened this past weekend when first Rose had pegged me, then the shemale Alyssa fucked my ass the next night, and both times I came from just the good, hard fuckings… thus sissy orgasms… thus ten points in a single kind of submissive act.
I hadn’t made a video of me sucking cock… nor would I ever.
A third five points also happened during my one and only real cock ass fucking when Alyssa had filled my asshole (or pussy) and triggered my sissy orgasm.
The next one threw me a little… since what defined public? I’d sucked BBC in a nominally public bathroom and in a classroom… so both were somewhat private… yet as I pondered this, I had to admit it would be hard to argue a public bathroom wasn’t public.
I definitely hadn’t sucked a friend’s cock… and most certainly not a family member’s!… a friend’s dad, yes… but not a friend. That said, I couldn’t claim it couldn’t ever happen, since having a friend I could suck every time I craved a cock and a load, such as Sammy for example, would be very fucking convenient, and given all the reports I’d heard about various of my teammates who also sucked cock and/or took it in the ass, who could say? We could quite possibly all run into each other and get it on at the upcoming Secret Cock Suckers and Cock Suckees (or whatever it was called… I hadn’t been told yet) Annual orgy!
And one final one that had occurred during my first real cock sodomy, as Rose had watched me suck Alyssa’s cock before she used it in my pussy.
Section 1: 3/8 (3 points)
Section 2: 8/12 (16 points) for a running total of 19/32
Section 3: 6/10 (18 points) for a running total of 37/62
Section 4: 2/6 (8 points) for a running total of 45/84
Section 5: 5/7 (25 points) for a total so far of 70/119
70 Points, and back up to almost 59%
Section 6: 6 Points Each
Got spit-roasted
Got fucked while girlfriend watched
Participated in a train
Participated in a bukkake
Ass to mouth, where you were the receiver in both holes
There were only five items in this section, and I’d only done two of them… although the other three all intrigued me… and I was even more intrigued after watching those sissy training videos.
Getting spit-roasted intrigued me.
Being the centerpiece of a train where cock after cock railed me, intrigued me.
Being surrounded by cock and taking load after load on my face and body intrigued me.
And this time, both of the ones I’d done came from my lone shemale sodomy:
-Rose had watched me getting fucked by Alyssa while I moaned like a bitch in heat, loving it, because the humiliation cascading through me only enhanced the pleasure.
-And then Alyssa had slid her cock into my mouth after depositing her load inside me, adding to my submission… adding to my humiliation… while I was on the receiving end of ass to mouth.
Section 1: 3/8 (3 points)
Section 2: 8/12 (16 points) for a running total of 19/32
Section 3: 6/10 (18 points) for a running total of 37/62
Section 4: 2/6 (8 points) for a running total of 45/84
Section 5: 5/7 (25 points) for a running total of 70/119
Section 6: 2/5 (12 points) for a total so far of 82/149
82 Points, back down to my being a tad over 55% sissy
Section 7: 7 Points Each
Made a video of getting fucked
Streamed having sex on a live site
Went out in public dressed completely as a woman, including full make-up, a wig, tits, hosiery and heels
Attended an all-male orgy
I hadn’t done any of those final four things… and only one of them had I imagined ever doing.
I had no interest in making a video, or streaming myself, or enduring a complete female makeover.
But as for the all-male orgy, I was certainly hoping to be part of a massive one next Saturday, which seemed a long time away at the moment.
Rose had taken me to a sex party and while I was there I’d taken part in some wild sexual encounters… but it hadn’t been an all-male orgy, even though except for arriving and leaving with Rose, I’d only interacted with men.
Section 1: 3/8 (3 points)
Section 2: 8/12 (16 points) for a running total of 19/32
Section 3: 6/10 (18 points) for a running total of 37/62
Section 4: 2/6 (8 points) for a running total of 45/84
Section 5: 5/7 (25 points) for a running total of 70/119
Section 6: 2/5 (12 points) for a running total of 82/149
Section 7: 0/4 (0 points) for a total 82/177
82 Points, all the way down to 43.6%
I realized that by the end I’d done 26 of the 52 sissy things listed, exactly half of them.
And I ended up scoring 82 out of a possible 177. I pulled out my phone to doublecheck that was still only 43.6%. Did that mean I was 43.6% sissy?
43.6% woman and 56.4% man?
As I pondered this, I noticed there was a legend for the scores. I scrolled down to it so I could see where my 82 points had landed me.
1-15: You’re not a sissy… perhaps you just had a moment of weakness.
16-30: You’re curious about beginning your sissification.
31-50: You like cock.
51-80: You love cock, and you get it anytime you can.
81-110: You want to be a sissy.
111-140: You’re well on your way to becoming a complete sissy.
140-173: You are a complete sissy.
My phone buzzed as I looked at the summary and saw the verdict.
A level higher than I would have picked… although I was almost at the very bottom end of it.
81-110: I wanted to be a sissy, but just barely.
That said, I had no interest in rising to any of the other levels, or even in scoring better in the level I was in. I certainly didn’t want to be a sissy the way it was described in this test… but according to my answers, I kind of did.
I glanced at my phone and saw it was from a number I didn’t recognize. I clicked on it.
Cocksucker. I’m in my truck just down the road. Get out here right now. Red truck.
I responded, even as my cock tingled in its cage at the anticipation of a cock to suck: Who is this?
A church goer.
I responded, as I scrambled out of my bed and pulled on my sweats: I’ll be right there.
Hurry up!
I slipped into some shoes, still in my pantyhose, and went outside. My parents were in their bedroom now, but their lights were still on.
I saw the truck just down the road and went towards it… recognizing it instantly. This was Mr. Mulroney… one of my buddy’s dads.
I got to the truck, climbed into the passenger seat, and he said only, his cock already out, “Get sucking.”
“Right here?” I asked dubiously, since with the light from the lampposts, we could easily be seen.
“Don’t be stupid. I’ll drive, you suck,” he said, as he snapped his fingers next to his cock.
“Yes, sir,” I said, as I tried to recall how many points car head had scored on the list. Just a few minutes ago I’d said I hadn’t ever done it.
I leaned down and took his hard cock in my mouth as he started driving.
It was so weird to be leaning in this position while I slowly sucked him.
“Oh yeah, nice and slow,” he praised, while I focused on his cock head.
I swirled my tongue as he drove slowly, savoring this cock… feeling so fucking horny. and craving some release after that sissy video and the sissy test.
“Yeah, you’re such a good cock sucker,” he said, enjoying my slow burn blow job.
“Mmmmmmmm,” I moaned on his cock, briefly adding some vibrations to the mix as I slowly sucked on only his cock head.
He slowed down and parked a moment after making a turn.
“We’re in an alley,” he reassured me. “Perfectly secluded.”
Again I moaned, since I didn’t want to take his cock out of my mouth.
“Shit, I can’t believe you’re so new to this,” he said. “It’s like you were born to suck dick.”
“Mmmmmmmm,” I again responded, trying to communicate I was born to suck his dick.
“God, I’d love to fuck that football player bottom,” he groaned. “Have you given that muscular back door up yet?”
So horny and definitely willing to get fucked, I responded, while taking more of his cock into my mouth, “Mmmmmm-hmmmmmm.”
“Is that a yes?” he asked, sounding surprised.
“Yes,” I replied, briefly taking his cock out of my mouth, enjoying giving ‘truck’ head, really enjoying sucking dick as he drove, and now willing to do even more if he wanted me to.
“You like it in the ass?” he asked.
“Yeah, but I’ve only taken two dicks in it,” I admitted, “although I’ve also used a couple of dildos on myself.”
“Then I think it’s high time we increased that number, don’t you?” he asked.
“I’m your slut, Mr. Mulroney,” I responded, addressing him so formally exciting me for some reason.
“Well,” he said, looking around cautiously, “let’s drive a little further into this alley.”
“Yes, sir,” I agreed, leaning down and resuming sucking his cock, keeping it hard for my pussy.
“Shit, who would have known our star linebacker is a complete faggot fuck toy,” he said, sounding just a little shocked to learn I wasn’t just a cock sucker, but a bottom bitch too.
He drove for only a few seconds before shutting off his truck and killing the lights. It was pitch dark.
“All right, let’s do this outside,” he said.
“Outside?” I asked, surprised, although I couldn’t see how else he’d manage to fuck me… although I quickly realized we could have gone into the backseat of his crew cab, except it was full of shit.
“Yeah, I’ll bend you over the tailgate,” he said, opening his door. “Hurry up.”
“Yes, sir,” I agreed, sitting up and getting out on my side.
We both felt our way to the back of the truck, me trembling with excitement and fear. If I’d been concerned about choosing wrong about public sex meaning in a public bathroom, this next activity would officially make my original assessment correct.
Reaching the back, he flipped the tailgate down and instructed, “Rest your hands on the tailgate.”
“Yes, Mr. Mulroney,” I said, again using the formal term.
“You like that I’m your friend’s dad, don’t you?” he asked, squeezing my ass.
“Yeah,” I admitted. “It’s a real turn-on.”
“I bet my son would either let you suck him or he’d fuck you,” he said, as he brought his hands to my sweats.
“I’m still in the closet,” I demurred, although if that was true, that closet door was pretty wide open by now.
He pulled my sweats down, touched my ass in the complete darkness and gasped, “Pantyhose?”
“Y-y-yeah, today’s the first day I’ve ever worn them,” I stammered, embarrassed to be caught in them, but happy I’d at least taken my panties off.
“Well, I’m sure your muscular ass would look extra cute and fuckable in them,” he said, as he glided his hands over my silky sheer ass.
“They’re my Mom’s,” I explained for some reason.
“Then I won’t rip a hole in them to access your cute asshole,” he said.
“Thanks,” I said, feeling so sexy, so feminine and so horny as he complimented and caressed me… although as usual my cock tried to rise up, and also as usual it was halted by a steel ceiling.
He pulled my pantyhose down to my ankles, well, my Mom’s pantyhose, and then pulled his pants down and directed his cock to my ass… thankfully not able to see the cage in the dark and in my bent over position.
“Shit, you really do have an ass made for fucking,” he said as he pulled my ass cheeks apart.
“Thank you, Mr. Mulroney,” I said weirdly. “I’ve had a dildo in my ass a lot tonight, so I should be gaped enough for your big cock.”
“You really are a muscle faggot,” he said, seeming to like that I was built like a man but willing to be used like a woman.
“Thank you,” I repeated again, readying myself for the inevitable pain-pleasure principle that was bound to occur once his cock slid into my ass.
After my ass being called a pussy throughout the training, I was a bit startled to hear him call it an ass. He positioned his cock at my hole and said, “I can’t believe I’m fucking a future NFL star.”
“Oooooh,” I moaned, as his cock slid into my asshole.
“So fucking tight,” he groaned, as his cock went deeper into me.
“Yes, Mr. Mulroney,” I moaned, “shove that big cock up my ass.” In truth it was pretty average, only about six inches, but he didn’t know he was small for me… since the dildo I’d been fucking myself with tonight was larger.
And for three or four minutes he fucked my ass… in the dark… in the alley….
If I wasn’t in a cage, I’m sure I would have had another sissy orgasm… and truth was, there was almost no pain in my ass… but considerable pain came from my throbbing cock desperately trying to get itself hard and be allowed to come.
“Oh yes, Mr. Mulroney, I love your dick in my pussy,” I moaned, as he was now really slamming into me and sounded like he was close.
“Pussy?” he asked. “You really are a little cock sucking, ass taking sissy, aren’t you?”
“Yes, Mr. Mulroney, my cunt was made to be used by strong dominant men like you,” I moaned, the pleasure so intense even as my clitty throbbed… referring to my cock as a clitty for the first time in my head.
He reached around to stroke my cock and found the cage. “What’s this?”
“My girlfriend makes me wear it,” I said, shame coursing through me, even though I wasn’t at all ashamed to be bent over the tailgate of Frankie’s dad’s truck with his dad’s dick buried balls deep in my pussy.
“Shit,” he said. “That’s a crying shame.”
“Not really. My purpose is to give pleasure,” I said, sounding like a line out of the sissy videos.
“Well, you’re certainly doing that,” he said, as he moved his hands back to my hips and resumed fucking me.
“Give me that dick, Mr. Mulroney, give it to me good,” I moaned.
“I’m going to come soon,” he said, a couple of deep, hard thrusts later.
“Breed me, Frankie’s Dad, breed me and make me your muscle sissy cum bucket,” I moaned, loving to belittle myself.
“Oh yeah, I’ll breed you, bitch,” he said, as he really fucked me, and as my cock ached with pulsing pleasure.
“Oh yes, Mr. Mulroney, fuck my pussy, breed my cunt, fill me with your manly load,” I babbled, dying to feel his cock erupt inside me… his cock rubbing against my prostate so good.
“Oh fuck, you dirty slut,” he grunted as he exploded deep inside me, keeping his dick all the way in as his cock pulsed inside me and he filled my bowels.
“Yes, Mr. Mulroney,” I moaned, as I exulted in the sensations of being filled, of his throbbing cock unloading and pulsing inside me.
“Yeah, boy,” he said, as he rested inside me.
After a minute, he pulled out and said, “My lad, that was amazing!”
“It really was,” I agreed, loving the hard fucking, even though I could feel a stint of blue balls coming… my constant inability to get hard was really wearing me down physically and mentally.
“I’d better get home,” he said as he pulled his pants up.
“Yeah, me too,” I said, standing up straight and feeling a little cum ooze out of my ass… which was such a slutty feeling. I pulled up Mom’s pantyhose and my sweats.
“I’ll drive you back,” he offered.
“Thanks,” I said, the aftermath of a sexual encounter with a guy always awkward.
We got back in the vehicle and he drove me the few blocks back to my place while I still felt cum leaking out of my ass and into the pantyhose.
As he stopped a few houses from mine, he said, “I hope we can do this again.”
“So do I,” I said, knowing I was no longer just a cock sucker… but I’d stepped up a level into being a willing two-hole slut for any cock.
I got out and went inside, wondering what this all meant.
I’d been pegged by Rose.
I’d been ass fucked by a shemale under Rose’s loving supervision.
Both of those experiences I could have defended as being part of an open, kinky relationship with the woman I loved.
But willingly going off with a guy, getting fucked in the ass, in the pussy, was definitely an entirely different level of kink… submission… and lust.
I got into bed, still in my clothes and Mom’s soiled pantyhose, and went to sleep trying to process what I’d just willingly done.
How good it had felt to be fucked.
How natural it had felt.
How it had made me feel so good inside.
How a load exploding in my ass/cunt had warmed my body the same way a load exploding in my mouth always did.
It had felt natural.
It had felt like home.
It had felt like I was born to do this.
Fuck!
I really was turning into a sissy!
THE END OF CHAPTER 10.