My Accidental Orgy

If you don't enjoy stories about oral sex, transwomen, sissy sex, or orgy situations, then you need to check out the Reader's Digest website, because that's all here, and a bit more.

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Hi! I'm Cassandra. Growing up in the 60s and 70s (in an Alaskan logging camp no less) I became very familiar with men's magazines and Penthouse Letters.

Before I move on with this story I should mention that I am a non-operative Transwoman. That means that I am, and always have been, a WOMAN; my body just didn't seem to have gotten the memo.

The letters Penthouse printed were always hot, usually so hot that most people said many of them were bull.

I can't send this one to Penthouse. It's not like anyone would believe it. I mean, while it was happening *I* could barely believe it!

But I assure you every word is true.

I had been married to a wonderful woman forever, if since the end of the Vietnam War is "forever" enough for you. Of course, I kept Cassandra as my little 'secret' before we married. "We" didn't meet until, of all things, the night before I went away to MCRD San Diego (that's the West Coast Marine Corps boot camp). And I must say she handled it admirably!

1.She was relieved; having found her closets moved about she was afraid that I might be looking for things to sell so I could buy drugs (romance and sex ARE my drug, I don't need to do anything else).

2.She quickly stuffed me into: one of her bras, a nightie, deep red lipstick, and proceeded to screw my brains out.

I didn't really have the vocabulary to define what I was (back in the 70s no gender issues were really even discussed) so I convinced myself that I was a Transvestite.

"If we divorce, or she died, I might consider full-time girl living." TV? Yeah, right!

It was 20 years later when I stopped lying to everyone, including myself! I didn't want to trade her for who I have to be. She had handled being married to a part-time girl with a roller coaster response. Some "let's play" days balanced with a good-old West Texas, "you're going to Hell" reaction. But she absolutely lost it when she was informed that she was, in fact, married to a woman! For a time I was even forced out of the house.

We both dated; I had my very first date with a man, and met my first cock, to "show my appreciation" for the evening. ... OK! He made me horny!

Her dates were similar but didn't satisfy, and we eventually got back together. She finally left me in February of last year. Oh, no! She didn't divorce me. Worse! She made me a widow.

I swore I never wanted another relationship. I couldn't stand being left behind again! But after 6 months, I couldn't take not being touched or held any more. So I went looking for a woman on Craigslist. No luck, but I did find lots of horny men. I tried a couple of them but that was a total bust. All dick and no heart or tenderness. Then it hit me: back in my TV days we met with several couples and single TVs at group functions. Many of these TVs (cross dressers) were miserable because they couldn't find a woman who would support them in their needs. I had always supported them by telling folks that "cross dressers make the best boyfriends and husbands!" That's it!

I put an ad on Craigslist for a SINGLE TV/CD who wanted to find a woman who would embrace their fem side. I found someone who sounded perfect! Married, oops! But hadn't dressed in 3 years. Come on over! The wife is out of town until Monday and I am inviting a few other CDs over. I thought "Great! Maybe they can lead me to a sweet hubby/bride."

And here is where it truly becomes unbelievable!

As I arrived I noticed a man going into the house. Hmmm. When I reached the door my hostess Lissa was providing the gent ahead of me (who looked exactly like Dwayne "Dog" 'The Bounty Hunter' Chapman) with a pair of panties. Ohhhh-Kay.

Lissa, who looks like a tall Samoan girl, met me with a hug followed by about 3 lip-locks. While I wasn't expecting that, it wasn't off-putting; it was actually rather nice.

I really didn't know how to conduct myself, especially since Lissa was over across the room swapping spit with "Dog". So I decided to play it cool and just grab a drink. The next thing I know, Lissa is on her knees with "Dog's" cock in her mouth. I was beginning to wonder how he qualified as a cross dresser. He was wearing the panties he had borrowed, but with his handlebar mustache and overall 'biker' persona he just didn't fit my idea of a cross dresser. Lissa didn't have a problem and seemed quite happy on her knees going down on "Dog".

Then she looked up at me and said, "Don't you want in on this?"

Well...heck. Ok, I guess. So I went over to him and he pulled me into a tight tongue-kiss! Now this was not my first tongue-rodeo, but it definitely was my first experience with a walrus mustache; a rather unique experience. However it wasn't nearly as distracting as his tongue reaching all the way down to my kneecaps!

I was just getting into the kisses (this guy did everything rough!) when he started pressing down on my shoulders; there was no mistaking his demand, and with "Dog" it was definitely a demand! However I consider myself to be rather good at this particular event.

I usually have no trouble taking control of the situation. A woman may look to be subservient being on her knees, but in reality she has a great deal of power over her hapless victim. To give or withhold pleasure is all in her...ahem...hands. I was in for a surprise though!

Guys really like eye contact when you go down on them. So as I slid to the floor I kept my eyes "adoringly" on his as I slipped his cock out of the sheer black panties our hostess had provided him. I was about to find out why he didn't look like a cross dresser, and why he had to borrow panties.

As my freshly painted lips slid down his very nice cock (I always enjoy the taste and velvety feel when I first taste fresh man-meat, and this one definitely qualified as a "real man") he ran his fingers through my hair. Ohhh, that felt nice. I closed my eyes in pleasure as I showed off a bit by deep-throating his rod. It was quite a bit larger than any of the playmates I had encountered since leaving Alaska. It was about nine inches long, and a tasty two+ inches thick.

Then he repeated the caress through my hair, until I felt him wrap my hair in his fist! While I am a woman, (yes my clit is a bit different from most of my sisters, but still) I'm not a Sissy. However, for the next ten minutes I was in for a crash course in "Sissy-Experience 101"!

Apparently with Sissies that eye - contact thing is writing a "blank check" to the Real Man that they are kneeling before. It says, "Please Sir, enjoy me!" Not knowing this I had just strapped myself on to the back of a bull when I wasn't even aware that there was a rodeo in town!

Using my hair to take control of me, and I do mean total control, "Dog" slammed my face against his pubes! The good thing was that since I had just relaxed myself to accommodate his tool I didn't gag. The bad thing was that this may have been the opposite of what he was hoping for. For a period of what seemed like forever he turned my throat into a pussy and continued to slam fuck my throat! By the third stroke I became aware that I had no more control over this scene than a cheap inflatable doll from a novelty shop!

At one point as he was ramming his manhood all the way home he completely cut off my air! I remembered not to panic and to breathe through my nose, but it was too little too late and the room started to grow fuzzy. Even trying to force myself back to gain breathing room was futile. However once he was sure that I had gotten the message, that he was the boss and I was his current fucktoy, he pulled back and let me catch my breath.

He loosed his iron grip on my hair and then *allowed* me to pleasure his cock. After a minute or two I began to enjoy it again. The taste and feel, the rush of being made a throat-pussy, tripped some switch in me and I began to enjoy him in my mouth again. I used all my best tricks. After just a few moments of my worshipping his Real Man's Cock, even knowing that I was just being given the "privilege" of doing so, I was thrilled to feel his cock swell, then jerk, swell even larger, and reward me with a flood of "man-cream"! [MY GOD! I nearly came just now remembering it!]

It was hot, salty/sweet, and abundant! Shot after shot pulsed from him; as if he had just been released from jail and hadn't cum in weeks. Perhaps he had though! The first two blasts went right down my throat but I backed up so I could taste his cream as it filled me. I had to swallow twice to keep from either drowning or losing his flow. Still I managed to get enough from the final seconds to fill my mouth to capacity. It was good! Or, perhaps, the realization that I was "back in control" made it more enjoyable. I looked up through my lashes at him and then showed him my mouthful of his man-juice, before making a show of swallowing every drop.

"Dog" grinned, and then the hair went tight as he used it to pull me to my feet and hold me in place as he forcefully ravished me with a kiss. As soon as he broke the kiss he pulled me back, locked eyes with me, and released his hold on my hair; then gently ran his fingers through it a couple more times as he watched for a reaction. He got one! I immediately found myself in 'heat' as I dove into his arms and passionately kissed him. I was no longer even a temporary Sissy, I was a woman again and as I joined my tongue with his to battle in his mouth, I was on fire!

Running my nails through his short, white, hair and grazing his scalp with my nails, we met in sex-crazed battle! The force and heat of each kiss was met and returned in equal measure. Finally, I kissed my way over to, just less-than-gently, bite his earlobe. He retaliated by kissing his way up and down my neck. That's my 'Kryptonite'! I instantly melted, softening all over (except for my clit in my panties). I suddenly found myself in another "first": as the "filling" inside a "kiss sandwich" between 'dog' and our hostess, Lissa. 'Dog' was back to enjoying my, now slightly bruised and puffy, lips as Lissa was feasting on neck, ears and shoulder as she fondled my breasts and lightly pinched my nipples. Even though I wear mastectomy breast forms due to massive weight loss a few years ago, I could actually feel the sensations as she stroked and pinched each breast, one after the other. My knees began to feel weak and "Dog" picked me up and carried me to the couch.

He told Lissa, "Give me a hand?" And between the two of them they removed my black, faux-velvet slacks, and shoes revealing my black one-piece garter belt/lace hose set and sheer black, backless panties. I also had a lacy black top over my black lace bra, but they left me these (some small comfort)!

He sat down on the couch, placing me across his lap as if I weighed nothing, a good trick as I am a solid girl, and again returned to assaulting my neck. Lissa knelt on the couch on the other side and did the same. I was going into overdrive! I had never been subjected to that much sensation at one time before; the kisses, "Dog" stroking my legs, and Lissa seemingly fixated on my breasts.

One thing I can say for "Dog" is that he's anything but boring! Having had his fill of feasting on my neck (and not a hickey left behind! A gentleman no less!) he slid out from under me, easy to do in his black leather pants, dropped between my knees, and tossed one lace-encased limb over each shoulder!

Uhhh guys?! VIRGIN IN THE HOUSE!! I had not expected to lose my cherry that night. True, to be safe I had douched the way a Domme girlfriend warned me to do, "Just in case, ya never know." But I *really* was hoping for something gentle and romantic for my first time! Somehow those terms and "Dog" didn't seem to be connected.

OooohhhhHhhHHH! I did NOT see that coming!! "Dog" had ripped away my poor panties (I guess he owns two pairs now) and was, with no warm-up or warning, tongue fucking my pussy! Dude! I will give you just...till...the end...of the WEEK...to stop that perver...oh god! Oh god that is... oh baby...don't stop!

But he did stop! "Heaven" was quickly replaced by two rough, bike-scarred fingers that were rapidly hammering my pussy! Less than a dozen strokes later it became THREE. And I don't remember any lube being added! Next came the interrogation! And me going back to copying Sissies I had seen!

"You're a whore, aren't you!? AREN'T YOU!? You'll fuck guys in alleys and anywhere, won't you SLUT!? WON'T YOU!!?"

"YES SIR!" and "YES DADDY!!" found their way from my lipsticked mouth without hesitation! I was in a frenzy and he was in total control, and he was definitely getting off on it!

He didn't take me with his cock, I am still technically a virgin. Though I did wind up being throat-fucked for about 3 minutes more until he erupted deep inside me, as Lissa was tonguing my clitty. His jets were hot as fire, but surprisingly sweet. As he shrank between my lips I milked every drop and licked him clean. He gently ran his fingers through my hair again before leaving, as Lissa crawled up on the couch to hold and snuggle me.

Dazed and a bit in shock I had to growl at my hostess, Lissa: "Hey! You KNEW what was going to happen! You threw me to the Wolf!"

"Yeah, Sistah! He was playing too rough for me! I hadda do sumpin'. Rest a bit, there's a nice young couple coming over soon."