“Veni, vidi et illa occurrit” Part 3

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It wasn’t that long after Rick (dressed as Ricki) left me at my hotel room that I got a text message from his wife Honey.

I had met Rick and Honey at a swingers’ club the day before, a Sunday afternoon. They were regulars at the club but it was their first time going to one of their TG and admirers parties. Dressed in matching S&M female outfits they had expected to be swarmed by the admirers and trans girls there. Quite the opposite. They had been shunned by most. They didn’t realize that our admirers all would be looking for t-girls who looked like real girls.

Then smelling a story I decided to talk with the couple and of course found that they were really nice people who just needed a little guidance and in return I might get a neat story for you readers. How do you like it so far?

To make a long story short Rick and I spent the next day shopping for femme clothes for him and having him get a makeover at the MAC counter of a large department store. We finished the day by giving him his first full transformation to Ricki and sending him home to Honey.

Honey’s text message read: “Who is this lovely woman and what have you done with my husband?”

I replied: “Do you like?

Honey: “She’s hot! Good thing I swing both ways because she wants to be all over me!”

Me: “Go to it girls. Just save some energy for tomorrow night.”

The next night Honey, Ricki and I were scheduled to return to the club for the weekly Tranny Tuesday party where we were to see whether Ricki had the right stuff to go all the way with one of the admirers. Apparently Rick particularly liked the taste of Honey on another man so he had a little experience. However he had not been one on one with another man. Remember this had all started because Rick had wanted to experience what it felt like for Honey to be ‘intimate’ with a man.

“It’s a big step,” I had told him, “the key is to be relaxed, to let your muscles relax. That takes practice.” I suggested he come over to my hotel Tuesday afternoon while Honey was at work and we could practice, loosen him up, so to speak. Then Honey could pick us up at the hotel and we could go to the party together.

It was one of those days when I had to work in drab in the morning. I was just back to the hotel and changed when there was Rick knocking on my room door. He had a suitcase with him.

“Hey, you’re early,” I said, “that’s great we’ll have lots of time to get ready.” But that was not what I was thinking. I was hungry and I wanted to take a nap. I decided to settle for one of the two. “Put your case down and let’s get a bite to eat. We’ll have a lot to do later.”

In the hotel restaurant Rick excitedly told me about his night with Honey. I wondered if anyone around us could hear him but I thought not. The restaurant wasn’t very busy. The day before, dressed as Ricki, my friend had arrived home with a half hour of anticipation building inside him. Remember that his previous crossdressing experiences had all been towards finishing with a sexual climax. In that way he was conditioned like one of Pavlov’s dogs, the ones that respond to a bell that signals food and they start salivating. At first they are salivating because of the food but soon it is the sound of the bell that has their mouths watering. Just like many of us at some time in our lives, he just had to put on the femme clothes to get very aroused. Heck at one point in my life for arousal to occur I just had to think about putting on a bra and panties. I knew what he had been feeling. I knew that I had only a few hours to get that feeling under control or we may never make it to the club. Somehow I had to de-condition Ricki.

Rick told me the rest of the details of the previous night, how he had modeled his dress for Honey and how she had been so receptive to Ricki’s advances. ‘TMI,’ I said but to no avail. It was only the arrival of our sandwiches that had any effect of curbing his enthusiastic re-telling.

“You did a lovely job on your nails,” I changed the subject. I was pretty sure the server had noticed the dark red lacquer but she had not batted an eye. In her business they see it all.

“You like? Honey did them for me last night. And she put on a clear base coat before applying the color, just like you said to do.”

“She did a great job,” I replied, “I should hire her to do mine.”

“Yours look great,” complimented Ricki, “how do you get them to grow so long? Are they real?”

“Yes they are real. I put the nail file to them every morning. Little chips will happen. Little chips will snag on something and become big cracks that cannot be repaired. A little preventive filing helps keep the little chips from becoming big ones.” I liked that Rick wanted to learn so much about the art of crossdressing.

Eventually we made our way back to my room, or should I say my suite. My status with that chain had earned me a free upgrade to a one-bedroom suite complete with mini-kitchen and oversized hot tub.

Rick was eager to get started with the makeover and I was eager to oblige but I had one more trick. I ran a nice very warm bath, complete with bath suds. I love that soft skin feeling. Rick was eagerly stripping and getting in the bath. Me? I don’t look so pretty when I’m naked so I discreetly slipped in to my favorite one-piece swim suit and slid in behind Rick. I picked up a bar of soap and started lathering him, first the back, then his chest and belly. When I got down below the waist I found him ready and waiting for me. Funny but it took me a long time to get his groin clean enough for my taste. He didn’t mind the care I took.

Suffice it to say that with all that warm water, cleaning, caressing and a bit more caressing Rick was overwhelmed with pleasure, if you know what I mean. Mission accomplished. I knew that he may be subdued for a while but for the evening we should be able to keep his anatomy and his sexual urges under control. It was a trick I used a lot in my younger days. You have heard of premature ejaculation. I called this preliminary ejaculation.

But suddenly Rick was alive with questions: how do you know when a man is liking what you are doing for him? What does it taste like? Does penetration hurt? How can you make it easier?

We had the time so I opened up to him. Of course I cannot go in to a lot of detail in this family oriented enterprise but I think you will know my references.

Imagine it is a warm day and you have been given a large ice cream cone, a two-scooper. Your best friend does not have one so naturally you do what?

“Share with him,” asked Rick.

“No silly, you tease him. At least that is what I would do. I’m going to stretch out the eating of the cone as long as possible. I’m going to want him begging for me to share the pleasure of the cone.”

I grabbed a handy banana shaped toy and held it to my mouth pretending it was the ice cream cone. “First I would gently lick my tongue across the top of the cone, just getting the slightest taste. Then I would run my tongue around the base of the top ice cream scoop. That fuses the two scoops together and makes the cone more solid.

“Oral is like that,” I continued, “You know there is an old saying in marketing — ‘sell the sizzle, not the steak.’ It’s the same in sex. Let the anticipation build in your partner. Let him believe how great it is going to be.”

“But how about at the other end?” asked Rick, “I have no experience there. Isn’t that going to hurt?”

“It can,” I said, “but I was going to show you a series of things I do to get ready for that just before I go out.” I went on to describe how I douche and use progressively larger toys to help me relax and get ready for whatever the night may bring. Also I lubricate, lots of lubricating.

After drinks and a bit more chatting Rick was prepared for his serious transition to Ricki. By serious I mean the makeup had to be just right, the Ivanka dress had to be spotless and smooth and complimented with just the right jewelry. I was going to chip in the jewelry and one of my favorite ash blonde Henry Margu wigs. Oh, I love that wig!

Honey was due to pick us up at 8:30. Ricki got me to take some pics with her phone. Then she sent them to Honey with the caption: ‘Meet U in hotel bar.’ Oh that girl was getting bold but she deserved to be. She looked great and she told me I did, too.

Truth is I think we both could have scored dates without even going to Tranny Tuesday. The hotel was hosting a convention of some sort of municipal workers and those old boys were looking for the experience of a lifetime. But not this time. Honey arrived and we were on our way.

The club is situated in an industrial part of the city, busy during the day but pretty quiet at night. We had no problem parking near the club which was a warehouse converted to a banquet hall converted to an adult play area.

We were among the first to arrive. We found a table where we could see and judge the later arrivers. We all had the same goal. We wanted to find the right person to take Ricki’s virginity. We had a bit of fun judging this guy and that guy. Other t-girls were not eliminated either.

Soon I slipped out of the game to meet up with an old friend. We chatted for a while and by the time I got back Honey and Ricki had decided on who Ricki was to seduce. Ricki turned to me. “Are you going to help me out?” she asked.

“Oh, no. You’re on your own. But he’s a nice guy, romantic but not too big,” I commented, “you will like each other.”

“But what if he doesn’t approach me,” Ricki asked.

“Approach you? Girl this is not the junior prom. This is a ‘tranny party.’ We are expected to pick and choose and make our approaches.”

“What should I say?’

“Anything you like. Ask to join him. Talk about the club. Talk about what you are wearing. Talk about football or hockey. Stay away from politics. I shouldn’t tell you this but that’s his business. At least that is what he told me.”

With drink in hand Ricki moved over to talk with her prey. I don’t know what she said but it worked. They were together from then on. Honey and I watched in amazement how well Ricki exhibited those flirtatious characteristics like the wave of her hair when she laughed at whatever he said, tapping her hand on his shoulder, sitting on the stool cross-legged so the hem of her dress rode up almost to reveal her garter belt.

Soon after the playrooms opened Ricki and her friend disappeared to the back. Honey and I waited a while before cruising back there ourselves. The action was not long in heating up. We looked for but could not find Ricki. She and her friend had chosen one of the private rooms but which one? It didn’t matter. Ricki was certainly going to find out what it felt like to be Honey. My job was done.

But what of the future? Would Rick be able to put the genie Ricki back in the bottle? Would his curiosity be satisfied now that he knew what ‘being a bottom’ was like? Or would he want more?

I never found out. We left the club around midnight. Ricki was quiet. After a quick change at my hotel so they could return my wig and jewelry the two were out the door and on their way home.

I never again heard from them.

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Tags: crossdressing, featured, sex

Category: Transgender Fun & Entertainment