Date with Ricky

On the next day my girlfriend and I went to the gym; as was our custom we both wore casually sexy outfits. My own collection of feminine clothes was slowly growing, so less and less often I had to borrow anything, either from her or from my sister. For the workout I also had my own outfit - pink yoga pants and white padded sports bra. Dani had a matching outfit, but with the colours reversed. We came to the gym primarily to exercise, but of course we wanted to use the opportunity to talk with Ricky. Before mentioning the anal sex we did a proper warm-up, set of exercises and stretching afterwards. All supervised by Ricky; as usual the supervising included a lot of touching, which by most people would be considered inappropriate. But most of the gym goers ogled us with pleasure and no-one complained. After showering and putting our sexy dresses back on we returned for a chat. As was to be expected Ricky eagerly accepted our proposal; we set up a ‘date’ for the next day.

“Still no kissing?” Ricky asked at the end.

“Oral and anal aren’t enough?” I replied in a teasing voice.

“Hey! I’m just asking. A man can hope, right?” he said with a grin.

For the date with Ricky we picked different ‘outfits’ for ourselves. Clothed sex looks good in porn, but in reality it is not so easy to find clothes which are comfortable enough for such activity. I did not want to be naked, because without the illusion of femininity I simply found sex with men unattractive. Dani agreed with me, although she looked at it from a different perspective; after all she was mostly an ‘active spectator’. The key elements of our outfits would be bodystockings; mine would be white, because we agreed that this colour fit me best, Dani’s - pink. Both items were crotchless, for obvious reasons, but for now we covered our crotches with sexy lace panties, in appropriate colours. This time I wanted my transition to be complete, so I glued pads to my chest and covered them with a lace bra (one that made a set with the panties). Dani and I also put on sexy makeup. All of these were mostly for our own pleasure, because Ricky was not overly attracted to femininity. My girlfriend and I also put on high heels and short dresses; to break the uniformity of colours Dani’s were white and mine - pink. These would most likely be temporary, but I did not want to greet my ‘boyfriend’ dressed only in lingerie. Underneath the clothes I was wearing an anal-plug. The same one that had prepared me for sex with Max. Ricky was also well-endowed, so such preparations were necessary.

When Ricky showed up I could see that he wanted to greet me with a kiss, but fortunately he respected my boundaries. He ‘restrained’ himself to touching my body instead. He eagerly groped my buttocks and even did so with my ‘breasts’. I did not know what Ricky's feelings towards boobs were in general, but for me it felt oddly attractive to have my artificial tits fondled; it further solidified my feminine persona. All three of us took light drinks and I explained in more detail to my ‘boyfriend’ what kind of experience I had with anal sex.

“All right, darling,” Ricky said when I finished talking, “I think it’s time for you to get down onto your knees and suck my cock.”

“I thought you came here to have anal,” I replied, surprised.

“That too,” he said with a grin, “but I don’t want it to be just a quickie. Plus you give really awesome blowjobs.”

“I’m easy to buy with compliments,” I replied with a smile.

I stood up from my chair, only to kneel down in front of Ricky. I still had all my clothes on when I retrieved his penis from his trousers and wrapped my pink-painted lips around its far head. Dani remained in her chair and watched my efforts closely. Initially I thought that Ricky just wanted me to get him ready for the real deal with my mouth. Once I made his penis fully erect and wet with my saliva, I stopped. Still fondling his large testicles, I asked in my best feminine voice:

“Ready, big boy?”

“Don’t stop,” he replied, “I want you to finish me with my mouth and swallow every drop. You won’t regret it, my second round will be even longer,” he added with a wink.

I just nodded, now understanding his motives and the reason in his arguments. I looked at Dani, she also nodded and smiled encouragingly. I could not say no to sucking a beautiful cock, so I eagerly resumed the blowjob. I no longer considered it a foreplay, so I sucked Ricky’s penis with the sole intention of making him cum. My own cock was also slightly erect, even though no-one had touched it yet; sheer excitement had that effect. I had to work for his seed for a few minutes, but it was pure pleasure for both sides. Naturally I had to deepthroat his penis too, not merely for the mutual pleasure of doing so. I also wanted Ricky to know that I was making progress on all fronts. Ultimately I swallowed his entire voluminous load and then licked the head of his cock clean.

“Damn, girl, you’re good!” Ricky said in a breathless voice.

He made a short pause, during which I stood up.

“There’s something I want to tell you, girls,” he continued, “a secret, so to speak. You see, I actually swing both ways. I maintain this flamboyant gay facade, so that women, my trainees, feel more comfortable in my presence. I hope that we feel comfortable enough in each other’s company that it won’t make a difference to you.”

Obviously it was fine with me, but I looked at Dani to learn her opinion.

“Sure,” she replied, smiling, “at least now we know why you like my girlfriend so much,” she added with a wink.

“Yeah,” Ricky agreed, turning his gaze from Dani to me, “you’re the best of both worlds.”

“I’m the best in general,” I replied with a wide grin.

“Of course you are. You mentioned pegging earlier. I was wondering whether you could do a little warm-up show for me.”

Dani and I looked at each other and smiled. Of course we were more than happy to do that.

“It might be time to take our dresses off,” my girlfriend said.

Now that we were aware of Ricky’s preferences we could make the striptease into a little show. Dani and I began to leisurely sway our bodies to an unheard music.I began to slowly peel her dress off her body; as my hands moved down I caressed her nylon-covered skin. My penis stirred inside of my panties. Eventually the dress landed on the floor and Dani gracefully stepped out of it; she then returned the favour. I could see the appreciation and lust in Ricky’s eyes; he was admiring both of us. Our panties went down in a similar fashion; this revealed my semi-erect cock which was already leaking pre-cum. But my penis would not be getting any attention just yet, Dani’s was; she had to put it on first though. I continued to dance for my one-man audience, while my girlfriend got the strapon from the cupboard and put it on; she also brought a bottle of lubricant. Once she was ready I laid on the bed on my back, raised my legs and put my knees by my sides; in moments like these I fully appreciated my hard-earned flexibility. While Dani lubricated my anus and her dildo the stiletto heels of my shoes were pointing at the ceiling; Ricky was watching us closely. The crotchlessness of my bodystocking finally showed its real value. I could have sex while remaining (mostly) dressed and thus feeling a lot more feminine. The fact that Dani looked really hot in her bodystocking was not irrelevant either.

My girlfriend aimed her plastic cock and inserted it into my ass with just the right speed and ****, she knew my capabilities perfectly; I issued a soft feminine moan. With the whole dildo inside of my ass she stroked my penis a few times. It reacted immediately, but she stopped before it became fully erect. Dani chose a moderate pace, after all this was supposed to be merely a warmup; and she surely knew how to warm me up. Every now and then she would reach out and stroke my cock; it never got the chance to become fully erect though. We maintained eye contact most of the time, but occasionally I glanced at Ricky. His eyes were glued to us and I could see the lust building behind them. After a few short minutes I noticed that he began to stir in his armchair.

“I think that our man is ready,” I said between the moans to no-one in particular.

Dani stopped with the dildo buried deep inside of my ass and turned around.

“Rested already?” she asked Ricky with a grin, looking at his crotch. His penis was slowly getting hard again.

“Almost,” he replied, “how about I touch that hot body a bit before we fuck,” he was answering her, but was of course talking about me.

“As you wish,” I said and my girlfriend withdrew the fake cock.

I stood up from the bed and slowly approached Ricky, I swayed my hips as I walked. He admired my body and motions, but apparently got impatient quickly. As soon as I got near and stood in a wide stance over his lap he reached out with his strong arms and grabbed my buttocks. Naturally I was expecting to be groped, but Ricky’s other action astonished me. Still holding my buttocks, he opened his mouth and took my cock into his mouth. I moaned softly and I thought that I heard Dani gasp in surprise.

Ricky continued to suck my penis, as his hands groped my ass and thighs. I got hard almost immediately, it was clear that he knew how to give blowjobs as well. I did not want to cum before the ass-fucking, but it felt too good, so I did not stop him. I also had a feeling that Dani was enjoying the new kind of show too. Fortunately Ricky stopped before I climaxed.

“Dont’ cum just yet," he said with a smile. Clearly we all wanted the same thing.

Still holding me closely, he stood up and turned me around. As my back was pressed against his muscular chest, he began to grope my ‘breasts’. It was an odd feeling, naturally the silicone pads did not transfer the sensation of being touched, so the physical aspect was limited, especially with my bra still on. But mentally it was arousing and it pleasantly enhanced my femininity; having your boobs appreciated does that, even if they are artificial. I could also feel Ricky’s cock getting hard, while it was pressed against my buttocks. Finally he stopped groping me and led me to the bed.