It has been a miserable year and a half following Covid-19. My sex life has been totally non-existent, except for some self-loving (let’s face it, a lot of self-loving). I decided I needed a substantial social break and to celebrate that I am still alive. I needed a party. No, not just any party but a sex-filled Halloween Party, no wait; make that a Sissyween Party. After all, let’s face it, Halloween is a sissy’s Christmas.
I don’t have many friends and none of which I would choose for sexual partners. More importantly, I have no friends that know I am a weekend sissy. So I decided to have my party with strangers, not just any strangers, all cross-dressers, sissies, trans/shemale, and the like. It was going to be hens party, hopefully with benefits.
Only one problem, I don’t know any like-minded gurls. After putting on my thinking cap, I came up with a plan. I opened up one of the searching apps for hookups. I did a 50-mile radius search for cd/trans. Jackpot over thirty names, only twenty-five had real pictures. I figured the rest were either lurkers or too shy about their sexuality and wouldn’t attend anyway.
So I drafted an email invitation to send to everyone that met my search criteria.
Next Thursday or Friday night, I am hosting an all-gurls Halloween party, or as I like to call it, Sissyween. I will be renting a room in a local hotel. I am inviting some of you ladies, cross-dressers, Trans, Sissies, she, they, them whatever you want to be called for a meet and greet: a night of non-judgemental fun, costumes, conversation, and lots of old fashioned debauchery. If you’re interested and, if so, which night works best, Please RSVP.
I pressed send on the email. It is too late now to change my mind. I am committed and should be committed! I have never appeared outside the house en femme. And now I am hosting a party full of strangers, dressed as a woman. I haven’t even come to the full realization of my new sexuality. I only began this journey shortly after Covid hit. I am still unsure if this is a mid-life crisis or where I want or need to be.
Within minutes I had my first response, “I would love to come. Friday works best for me.” Definitely, I am committed now! Responses continued to come through the next two days. I was constantly checking my mail to the point that it was an obsessive behavior.
After two days, I had thirteen positive responses. Seems like everyone needs a break or a party. Crap, this is for real. I need to make some preparations.
So many things to do:
I booked a hotel with adjoining suites.
What was I going to wear? The decision was easy since I was the hostess. I would be the ultimate Halloween hostess: Elvira Mistress of the Dark. Shopping at the local Goodwill store, I found a long slinky black dress that I could cut a long slit into. I figured the shoes must be unique. I chose a real pair of catch me, fuck me, shoes. They were 5-inch black platform pumps, peep toe, sandals with bows, and zippers. I selected my best lingerie, featuring a Rago black corset with eight garter straps.
Makeup, not my strong point. Usually, when I try to apply makeup, I look like a zombie with black eyes. That won’t work for the party. On second thought, that just might work. I was off to the drug store for new makeup and brushes. I practiced every night till the party.
I drafted a new email confirming the party, location, time and established a few rules:
At the party you must be en femme, you can change here if you need.
Have fun, let your hair down, so to speak
Please don’t be shy, be who you want to be.
Bring your condoms, toys, etc. Unfortunately, no bareback action (do that on your own time)
Don’t leave anyone out. We don’t want wallflowers. We here all for the same reason, this is a non-judgemental party
Just like fight club, no one talks about the party
Finally, since I have a huge stocking fetish, everyone must wear gartered stockings or thigh hi’s. Stealing a page from Literotica’s famous author Silkstockingslover. Stockings will be colored coded:
Nude: I don’t want to participate at this time; I just want to watch
Pink: I just want to suck cock
Gray: I just want my cock sucked
Mocha: Peg or fuck me
Black: I want to be air-gapped
Red: gangbang me, please
Other colors: Ask me
If any of this offends you or you want to change your mind about attending, let me know.
I got a few responses, mostly confirming they would be there. No negatives replies and several gurls were commenting how they loved the stockings idea.
The week just flew by. I was finding out that I was horny all week just thinking about the party. I edged and denied myself every day. I came so close to cumming on multiple occasions. I thought I would explode if I didn’t get relief soon.
On the day of the party, I was a busy girl. First, I was off to the store to get necessities, decorations, snacks, water, a case of Rose wine, condoms, several bottles of lube. I went to the adult bookstore to pick up a couple of dildos, strap-ons, party favors, and gifts for prizes.
Next, it was to the nail salon. I have never had a pedicure. If ever I was feeling gurly enough to warrant a Pedi, it was today. I was not going to go with polish but just get a clean-up. But then, I looked at the girl next to me. She was getting beautiful red nail polish on her toes. I asked the beautician for the same, she also recommended press on nails and painted them the same color.
After checking in to the hotel, I hauled all my goodies to the room. It was a gorgeous suite with multiple bedrooms. I began setting up the table for the refreshments, name tags of all the girls laid out, bottles of lube, and spread toys throughout the room. I put out a bunch of Halloween decorations. I even hung a sheet with a Gloryhole cutout on the closet entrance.
After the room was finished. It was my turn. I drew a bubble bath, shaving my body and relaxing the best I could. I could not tell if I was more nervous or excited. Getting out, I patted myself dry and put on my makeup, and dressed. In case you’re wondering, I was wearing black stockings. I looked in the mirror. I couldn’t be happier, I got the makeup just right, and I thought to myself, “I would fuck me.”
I was ready to meet and greet my guest. I no sooner had poured myself a glass of wine and sat down that I heard the prearranged knock signal. It was 30 minutes early. My heart jumped to my throat. I opened the door to a gentleman of medium height, who apologized for being early but wanted enough time to change. I guided him to the bathroom.
He told me I looked beautiful, I knew he was exaggerating, but I beamed with gratitude.
The knocks kept coming over the next 45 minutes. I greeted everyone personally. I was very impressed, we had some drop-dead beautiful gurls, some fantastic costumes, and some of not so much But everyone put in a lot of effort. Best of all, not a pair of nude stockings in the bunch. Like, skittles we did, however, have a rainbow of colors.
The costumes ranged from two Wonder Women, Supergirl, three sissy maids, a sailor, vampiress, schoolgirl, Harley Quinn, Sluty nurse, witch, and the man who came early was Catherine the Great.
As I looked around the room, I noticed some conversations, some milling about, and maybe a hand on a knee or thigh. But we needed to do something to get the party started. I created the ultimate ice breaker, in my opinion.
Okay, gurls, get in a line facing me, okay now taking a cue from the movie “Trading Places,” I want you all to reach out with your left hand and grab and massage the ass to your left. With your right hand, I want you to grope the clitty on your right. I went and stood on the far right so the last person would have a clitty to grope. After about 30 seconds.
Okay, gurls, I directed “move around and switch places with others and repeat the process. We did this one more time. ”
Now that we have been appropriately introduced, let us play another game. Please break off into two lines facing each other. I gave everyone a blindfold, and I shuffled them around. Keeping track of who was where.
Okay, the instructions are as follows. When I say go, the group on my left will drop to their knees and start sucking the cock in front of you. After 60 seconds, you will be directed to stop and change positions. The other gurl will drop and suck. We will do this for 2 rounds. In the end, you will be asked to guess you sucked and who serviced you. Also, if anyone cums in the 60 second period, you will be penalized and pay $10 to the refreshment kitty.
If you do not want to play, raise your hand now. No one moved; I started the game. Watching it was sort of amusing but arousing as hell. I had all these people sucking cock on my command. To think, I always thought I was submissive or had wanted to be. It must be the outfit.
No one could correctly guess every dick they had sucked. Everyone got the biggest and shortest cocks right, so I decided to give those two the prizes. I had recieved enough money to pay for most of the refreshments except for the wine.
Gurls, that’s it for formal introductions. I ask that you “mingle” amongst yourselves. I would recommend changing acquaintances every 20 or 30 minutes. Think of this as similar to speed dating. If you find someone you really like, you can meet with them later. Everyone started pairing or grouping up.
I walked up to this pretty little blond sissy; she was dressed head to toe in a pink maids outfit. I guessed she was maybe pushing her upper 30’s, about 5’6″. A real cute little package, but then I am a little older and not as cute. We started talking, she was enjoying the party. She wished she could have worn pantyhose instead. But she was getting used to the stockings. She was just too damn cute. All of a sudden, I heard myself saying.
“Get on your knees slut, and suck my clit!” I demanded
Whoa, where did that come from? I wondered. She dropped and grabbed my cock and went to work on it. Damn, she sucked a good dick. After a couple of minutes, I told her I was going to cum, and I asked where she wanted it?
“On my face,” she exclaimed, I complied, and she didn’t wash it off all night. Later in the evening, I noticed her on the couch, being spanked, by the sailor.
We did have several other above-average cocks.The only gurl with a nine or ten-inch clit, Supergirl was very popular. I never did get a chance to suck or fuck that one.
I watched both Wonder Women sixty-nine each other, it was beautiful.
For the next three hours, I’ve never sucked or been sucked by so many people. It seemed like everywhere I looked, as one orifice emptied, another cock would fill it. I thought to myself, these gurls are hungry. COVID must have seriously impacted their sex drives.
Katherine the Great lived up to the sexual reputation. She was being gangbanged by nearly everyone and was looking for more.
Without me knowing it, someone had ordered food from grub-hub. A tall, handsome young man, maybe eighteen years old, delivered it. I answered the door in only my lingerie, thinking it was a late arrival. I shouted, Does someone want to pay him and give him a proper tip? He just dropped the food and ran. I laughed.
At one point, I was on top in a sixty-nine position with a very adorable Vampiressl. She had a very cute downward curved cock that fit perfectly in my mouth. I was just getting in the groove when I felt someone lubing up my behind. The next thing I knew, I was experiencing a feeling that I have wanted to feel all year, two nice cocks in me, at the same time. Once the mysterious cock was all the way in, I found myself rocking back and forth between the two cocks. I was like a toddler on a rocking horse. Before I knew what was happening, my left leg was shaking, my cock exploded in the gurl’s mouth, and I collapsed, totally fucked.
I never did know who had taken my virginity. It took me a while to recover from my first sissygasm ever. I looked around the room bodies were everywhere; clothes, costumes, and high heels were strung from one end to the other. It was just after 1:00am. I informed everyone it was getting late, and it was time to go.
I felt that everyone had gotten their fantasies fulfilled that night. If they didn’t, it was their own fault.
As they all gathered their items. I informed them that we would do this again next month, with guests allowed, and there would $100 bounty for whoever brought the largest cock. I kissed everyone on the cheek and grabbed their balls as they left. Damn, that one cock was huge. Maybe next time, I sighed.