In our on-going Sissy Cruise Blog Train, what a day yesterday with Mistress Harper and the Sissy Games on Deck! She got you sissies all pretty with manicures, makeup and even dressed for the evening and that readies you for my special treat for you tonight. Tonight, my sissy is losing her virginity!
With all that prettiness you have, now you are telling me you are a virgin? That you have never been deflowered by a person (man or woman)? Well, we will just have to take care of that, sister.
Let’s take your pretty sissy self out to the club so you can show off how sexy you are and how good you feel. Drink if you want to, but remember they charge you for alcohol on cruises! Don’t want to go in the hole at the bank for a couple of drinks. You could have a Virgin Strawberry Daiquiri, though. Great to stick to the theme of the entire night, don’t you think?
Sissy In the Dance Club
I am thinking we need to go to the Dance on the Deck night tonight!
We joined the throngs of people on the deck, each of us ordering a drink. I made sure my sissyfriend’s was a Virgin… Margarita is what she had.
She looked so pretty after her day with playing games with Mistress Harper, I wanted to show her off. We wandered from person to person and I introduced her to each of my friends and even to strangers. After each one, I would whisper in her ear, “Would you like losing your virginity to that guy?” and she would giggle until she realized I was damn serious in what I was asking.
You Seriously Want Me Losing My Virginity?
“You bet your sweet pussy I do!”
I think then, if she had not already been sober, she would have sobered right up knowing I really had in mine to get someone to take her virginity.
You see, my sissyfriend LOVES to suck cock. I have been with her, watching her suck one after another at friends’ parties. I mean, she really is a slutty bitch!
But she’s always been protective of her pussy.
“It’ll hurt,” she’d whine.
“And?!” I would reply.
What About You?
Then she got a wild idea of losing her virginity with me!
Well, it isn’t like I had never taken someone’s virginity before or anything, but I had been actively looking for someone else to do the delicious deed.
Instead, I took her into my cabin, dug my harness and dildo out from my luggage, strapped it on and then proceeded to ravish my sissyfriend’s pussy.
Well, if you must know the truth, I was gentle and slow and respectful and I used a TON of lube. In the end, she lay in ecstasy between the white sheets and I cradled her in my arms as she fell asleep.
Tomorrow, Mistress Audrey takes her place on the Sissy Cruise!
Mistress Daphne, your seagoing sissy will wake tomorrow to a whole new world now that she has had her virginal rosebud taken in such a sensual adventure.
“Damn the torpedoes…full speed ahead!” she will proclaim…actually now that Pandora’s box has been opened, as it were, it will be more like “I want torpedoes…full speed ahead!”
Every sissy remembers willingly giving themselves to a loving Mistress and the amazing moments as your satin chemise is raised your panties removed and your stockinged legs slowly spread apart to let in a brand new world. Sigh….
Mistress Daphne although I am sure I don’t have to remind you, keep a close on your sissy gurl for the remainder of the cruise.
Now that she has spread her wings she will be back at the club in her search for more faster than you can say “Jack Sparrow”!
(and she won’t have to worry about buying her drinks!)
I sure pray you are a writer, little davey, because you are A-MAZE-ING at it!
I love everything you said about keeping an eye on her and how much she will want repeat performances. You are totally spot on.
laughing so much at your visuals
You are great!
If you’d like I could help you to keep an eye on her. Arm me with a spyglass and send me up to the crows nest for observation!
The sight of me in my heels and short skirt climbing up the mast… (not the first mast I’ve climbed…or slid down!) may distract your sissy’s amorous suitors long enough for you to bring her back into the fold!
I am laughing so delighted at your play on words and your lilt of language.
I love the idea of you on the mast… humping it maybe?
You are great!
I have a great cabin on the Sissy Cruise….Mistresses Willow, Brighton, Erika,Harper and Daphne all have cabins on my deck… and my door doesn’t have a lock…(I actually don’t have a door…cum sail away!). Where are the sissies? Happy Anniversary Get Girlie
Mistress Daphne hearing your laugh knowing you’re amused must at least assure me of one more “port of call” on the Sissy Cruise!
I shall heed your warning, little davey. You are very wise!
Mistress Daphne, I loved your Sissy Cruise post today – a true Sissy fantasy if I ever read one!
Thank you, Ms. Audrey! So glad you enjoyed it.
Thrilled for your sissy
As crawl out of the life boat
And start my walk of shame back to my cabin an catch up on the an amazing cruise
I love poetry.
Walk of Shame… tsk tsk
Deflowered by Miss Daphne on the high seas sounds like just what sissies need to help them come out of their shell, so to speak. Sounds like sissy got a pegging she won’t forget. 😉
Thank you, sweet Duchess!
I think she did, too!