Maria Ch. 02: Continuing Explorations

Continuing Explorations - with Gina?

After that first night with Maria, I was a bit confused about how I felt about what had happened, but rapidly decided that I wanted to see her again, and experience more of it.

I called her later that day, to thank her for a wild night and to make plans to see her again – as soon and as often as possible.

On our second date, we were talking over dinner about how she had completely drained me during our first night together, and then had me cumming again, even with no semen left in my balls. She told me that she had just been trying to give me as many orgasms as I had given her, and then laughingly challenged me to see how many times I could bring her to orgasm before I passed out. Once again, we rushed back to her place, eager to get naked together. We started out with my face buried in her pussy while I was still fully clothed. I couldn't help but think of the Sam Kinnison comedy sketch about "licking the alphabet", "writing a letter with your tongue", and "making her cum twice before she even sees your dick" – good advice on any date, but I was going for much more than two.

Once again, I was able to bring her to a rolling series of orgasms while licking, tonguing, kissing, and sucking on her labia and clit. She reached a point where I backed my glazed face away an inch and was able to bring her to further orgasms by just blowing softly on her sweet, inflamed pussy. She later joked that this was the first time she had ever been on the receiving end of a "blow job".

The pussy eating continued for hours, including several changes of position, and me stripping off my clothing while she was panting for air. The highlight, for me, was when her thighs were wrapped around my ears, and she had both hands pushing my face into her crotch as she ground against my lips and tongue – I was delirious with pleasure as I served her and gave her that much joy. I'm not sure exactly when it happened, but I apparently came while eating her pussy, came without either of us touching my cock. My boxers were soaked with what I was assuming was precum, until Maria told me to lick them clean, and I realized that there were thick globs of semen there, too.

The evening concluded with me fucking Maria, dumping a load in her ass and then having her get me hard while wiping my cock off with a warm washcloth, and then sucking my cock and fisting my ass until I came again, filling her mouth with my third, and final, load of the night – which she made sure to share with me during a deep kiss.

I was able to see her one more time – a total of three times over two weeks. On that third night, there was a point where Maria had left the room to go to the bathroom right in the middle of fisting my ass and blowing me. Maria sent her transgendered roommate Gina into the room so that she and I could suck each other off in a wild sixty-nine that left both of us drained and breathless. Maria stood in the doorway, fingering herself to orgasm as she watched. She then had Gina fuck her, and had me lick Gina's cum out of her pussy as Gina got her rocks off for a third time while fucking my ass – which Maria had stretched out earlier.

Other than telling me that she had gotten back together with her ex, and so couldn't see me any more, I never heard from Maria after those three dates, even though I would occasionally send a friendly, nonsexual "How are you doing?" email. But I did hear from Gina, quite unexpectedly, over a year later.

During that intervening year, my life had changed dramatically. I had been deployed with my Reserve unit and a work related event had caused me to suffer nerve damage, and it changed what I was able to do. Any strenuous physical activity would now result in severe vertigo attacks, which left me twitching helplessly on the ground. I had to spend months in recovery, learning my new limits and capabilities, finding the right levels and mixes of medications, and going through physical rehabilitation. I had been dating a woman named Josie, who I will try to write about in a different story, who broke up with me when she discovered that, with my disability, I often had trouble "finishing up" our very vigorous sexual activities.

It was while I was still recovering (physically from the disabling event, emotionally form losing Josie) that I got an email from Gina. At first, I wasn't sure who it was form, since Gina and I had never exchanged contact information (just loads of cum), but I recognized her references to Maria. Gina had invited me to attend a "shemale" party as her guest. I decided to give it a try since it seemed like a guarantee of sex – especially when she asked me to bring proof that I was HIV negative. I was really turned on at the thought of fucking, and being fucked, by Gina, without a condom.

I met Gina at a lounge near the hotel, so we could have a drink before going to the party, and I could give her the results of my most recent HIV test (negative), as she had asked (she also showed me hers). As I remembered, she was a larger "girl", and not fabulous looking – or very passable in full lighting. But I remembered her as being a lot of fun in bed, and so got over my fear of being seen in public with her – after all, it was unlikely that I would run into anyone that I knew at a place way out by the airport.

Gina and I talked a bit about old times before heading over to the party.

"I really wish Maria had kept seeing you," Gina told me. "The guy she got back together with is a real jerk. If he didn't have such a good job and such a big cock, I don't think Maria would stay with him. I'm surprised she never called you up for a repeat visit – I know I suggested it to her every time she and her new guy got in a fight and 'broke up' for a few days. I'm just glad she finally gave me your email address, but I wasn't sure if you'd want to see me, or even remember me, so I never emailed – until this party came up."

"I would have been happy to hear from you earlier, Gina." I said, trying to be gallant, even though we both knew that she wasn't anywhere near as attractive as Maria. "I always enjoyed the time we spent together."

"Enjoyed my cock is more like it." She responded. "Not all guys like it when a girl like me wants to use her 'clit' for some pleasure. I appreciate that you seem more than willing to give pleasure as well as receive it – which is why I thought you'd like this party."

"So what exactly is the party for? Is it a special occasion, someone's birthday? How do you know the other couples there?"

"Other couples? I'm sorry, I thought you knew. While we are going to arrive together, and I certainly hope to spend some time with you at the party, it isn't for couples. This is a sex party, you might call it an 'orgy', for transwomen and the men who appreciate them – and I think you appreciate them more than most. Most of the people are single, but men don't get invited without a reference. I thought I'd invite you, partly to get another chance to be with you, but also because I think you'll enjoy meeting the other girls, as well."

And so there I was, in a darkened suite at a hotel near the airport, sucking off Gina shortly after arriving, while she sucked off a well hung black guy whose name I never learned, nor needed to know. It was exciting to watch, as well as to participate in, the many sexual acts going on in the two room suite. In addition to watching Gina suck that giant black cock while I was sucking her, I also got to watch him fucking her ass, and got to admire the beauty and technique of several other "girls" – as well as admiring the cocks that they carried on their sexy, and otherwise feminine bodies.

I had experimented a little with transwomen before (Gina, a "girl" I met at a gay bar, and a "girl" I had unknowingly made out with pretty heavily at a party during my college years, but had fled from when I realized that she had a cock) and enjoyed quite a few fantasies while alone and stroking myself, but this night turned me into a true fan of transwomen.

After my experiences with Josie, I wasn't sure that my cock could be relied on to stay hard throughout any sex – particularly any fucking, so I wandered, watched, sucked off a few of the girls, and let some playfully suck me for just a while at a time – usually either as part of flirting, or while they were getting fucked. I wandered from one person, couple, or clump to another, getting very excited by the action on display, and enjoying having girls flirtatiously lick and kiss the precum form my dick, and then kiss me and move on, suggesting we might want to finish later. Several were a bit surprised that I was not just willing to kiss them back, but obviously enjoying open mouthed kisses, even after they had been sucking cock.

I spent quite a bit of time making out with "Joy", a petite Filipina that really reminded me of Maria (Gina made the same observation) but who had a nice, brown, medium large cock that spurted two sweet, creamy loads into my mouth that evening, and who liked having me lick her ass to "soothe it" between rounds of being fucked by other guys.

Since I was not just there to pump a few loads into a sexy mouth or ass or two, and then leave, I was able to stay active through most of the night – until many of the men had gone home, and many of the girls had either gone home or gone to bed. We finished the night with Gina's cock in my ass, the first time she barebacked me. It felt great – the bare flesh didn't create as much painful friction as a condom covered cock did, and the precum kept things well lubed – plus I loved the feeling of her hot cum shooting deep into me.

"That was hot – and not something I see at these parties very often." Said a cute Asian lady who had been stroking her small cock while watching. "I'm Gloria, the one who organizes these parties. Care to suck my 'clit'? I'll suck you afterwards – I don't like to sixty-nine, it's too distracting." I looked at Gina, who was dressing and gathering her things.

"You go ahead, hon'." Gina told me, as she smiled and nodded. "I told you that I brought you here so you could make new friends."

Most of the guys at the party were there to be sucked, or to fuck girls' asses. I seemed to be the only one who was interested in sucking the girls off – which made me popular with the girls that enjoyed that. I enjoyed swallowing loads from Gina, Joy, and Gloria, as well as several other "girls" over the course of the evening, and Gloria exchanged emails with me and invited me back.

One regular feature of the parties was that if Joy was there, she and I would always make out for an extended time, and she would always give me all her cum, but would never give me her contact information, or agree to see me outside of the parties (I was very much smitten with Joy, to the point of imagining myself marrying her), Joy would suck off other guys who would be quite aggressive about holding her hair and face-fucking her, allow them to violently fuck her sweet ass, and also watch me orally servicing other girls (and later in the evening, at some of the parties, some of the guys as well), holding my head and pushing me down on their cocks so that they went deep into my throat, knowing that I liked to be treated the same way that she did while servicing cock. I tried fucking Joy a few times, but was not able to keep an erection through the aggressive style of fucking that she enjoyed while wearing a condom (I even went into a vertigo episode once while trying it), but she would often suck my cock (an act where I was able to simply relax and enjoy the sensations until I came), and even fucked my ass a few times (although she didn't fuck me bareback, like Gina did, I still loved having Joy inside me) .

Gloria always quietly let the girls know that if they wanted to fuck a guy, my ass would be available at the end of the night, once things had quieted down, and most of the guests had gone home. So I'd get fucked by at least one, and on one night an amazing (and somewhat bruising) four girl-cocks at each party. Every party also ended with Gloria feeding me a load of her creamy goodness before I kissed her goodbye.

I attended the parties (which took place every month or two at first, then dwindled into every three or four moths) regularly for two years, until I got involved in a relationship that I thought was going to lead to marriage (but ended after a year of living together in a monogamous heterosexual relationship with vanilla sex – pretty much just the missionary position - managed only by using the little blue pills) . After that relationship ended, I was unable to get back into the loop of the parties – and am not sure if they were still going on. Emails to Gloria went unanswered and Gina had already stopped attending, before I did, because she got engaged. I still dream about finding Joy again, and having a real relationship with her – or at least rekindling the series of wonderful interludes we had enjoyed at those parties.