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!

Virginity? Seriously?

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?


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Sissy In the Dance Club

I am thinking we need to go to the Dance on the Deck night tonight!

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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.

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You Seriously Want Me Losing My Virginity?

“You bet your sweet pussy I do!”

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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!

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Onward Ho!

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.

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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.

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Tomorrow, Mistress Audrey takes her place on the Sissy Cruise!

Happy Sweet 16th Birthday, Get Girlie!