A Night of Firsts

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The ongoing adventures of Rob, transgirl May and little Andi

This is a continuance of my story "Rob Finally Does It"

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"Well, yes. I thought you'd never ask!" May replied lovingly with a touch of sarcasm. I could feel Mays' cock explore a bit deeper. "Mmmm. You feel so good wrapped around my cock. Yes, I am going to fuck you now. Are you ready?"

May, at that point, really didn't care if I was ready or not. OK, she cared, but she didn't. Balls deep in my ass, she already knew that I wanted her and we were now completing the loving connection she had so desired. Both of us wanted her orgasm. I could feel her cock pulsating against my prostrate as she held it firmly in my butt and I myself began to respond. I ground into the bed, wetting it up with precum. I was soon as hard as a rock.

"Ah, yes, move for me. Oh no. No, no, stop! You're gonna make me come too soon!" May whispered, kissing me with a giggle.

"I love you May," I said as I continued my slow grind, ignoring her, "Come. Come in my ass. I want to feel you squirt."

"Stop it! You're gonna make me come. You're gonna make me come. Stop! Oh!" May gasped. I could tell that she was trying to hold back, but I wouldn't let her. I kept it up. Plus, it felt nice moving my cock against the sheets and I liked the fullness of May's cock in my ass and knowing that it was hers. I was surprised that May was so close, so soon. She and I could fuck Andi for what seemed like hours and I would almost always finish before her, regardless of which of Andi's holes either of us happened to be in.

May was on the edge, she was getting nearer and nearer with each of my subtle movements. As she retreated to set up a thrust, I squeezed her as hard as I could. I wanted her to feel that slippery tightness that she had so often provided me. I loved her and I was going to make her come. I reflected in the moment of what a good job that Andi had done lubing me up for my first time.

With a final, pinning, but gentle thrust, May unloaded deep in my ass. "Ughhh, oh God. Ughhh!" she grunted as I felt her cock repeatedly pulse and deliver while May continued to push as deep as she could. I could feel the bulbous head of her cock expand and contract as it involuntarily pumped again and again. It was fun for me to hear and feel her lose control of her body as she ground both me and my cock further into the bed and with her cock as far as it could go up my ass. She hugged me and kissed my neck as she came and I felt her gradually soften. My anus then thrust the head of her cock out of my ass as May pushed off of me. She then smacked me hard on my ass with one hand as she spread my cheeks with the other.

"Hey! What was that for?" I asked.

"Your tight, virgin ass made me come too soon! But now you owe me. Come on, come on, let me see it, let me see it! You always do this to me! I'm just paying you back!" May replied with a laugh.

"Ok, ok. I get it. You're so bad! But you're in trouble now because I have a great hard on!" I said laughingly. May was a real cum machine. She would, more often than not, come hard and with volume. Judging from her immobilizing pin of me to the bed and from her relentless, pumping squirts, this one had to be another of her "good ones". But there was really only one way to find out.

I would now have the new experience of squirting cum out of my ass. May's cum. I got on all fours for some leverage and bore down. My ass was embarrassingly audible as I expelled May's creamy ecstasy and I could feel its warmth slithering down my balls. It felt like quite a bit, but I could only imagine what it all looked like down at the other end.

May started to say something, but our post orgasm assessment was interrupted by us hearing a giggle coming from the other side of the bedroom door. Andi. Fucking Andi must have been listening the whole time, that little shit. May and I started laughing. She hopped off the bed and opened the door with a giant smile, her limp cock glistening in the candlelight. Sure enough. Andi.

"Andi, you're a bad little girl!" May said playfully. In a surprising display of dominance, May grabbed little Andi by her hair and shuffled her over to the bed. I was still on all fours, craning to see the spectacle, but I was afraid of making more of a mess by getting up.

"Well, Andi, since you want to be part of the action, you can clean up the mess," May said laughing while directing Andi's head inches away from my drooling asshole. Andi was giggling the whole time, but she dutifully complied with the clean up order by licking my balls and asshole. She deliberately nipped my balls with her teeth and circled my slimy anus with multiple orbits of her tongue. She also used some of the goo to stroke my unsatisfied cock, thus bringing it back to fully ready.

"So, which one of us are you going to fuck, Rob?" Andi inquired, "I hope you're not going to waste this on May!" May smacked Andi's ass. Andi giggled.

"I have a better idea!" May exclaimed. She turned me over on the bed against the pillow pile so that I was almost sitting and then wrapped a sheet around my head, blindfolding me.

"Come on Andi!" May said as I felt her velvety tongue glide over my cockhead, licking up some precum. I then felt another pair of lips and a tongue as talented Andi joined in. While Andi was the true cock suck pro, it was really hard to tell exactly who was who as May was doing a surprisingly good job of keeping up. This was another first in my relationship with these two; strangely, they had never before administered a double blow job. A night of firsts for me.

I felt a hand grasp the base of my cock, while another cupped and massaged my balls. Then a pair slimy tongues on each side going up from the base to the head, stopping there for some licks underneath and a hard suck. A couple more teasing flicks here and there and then an exquisite display of deepthroat, first by one and then the other followed by a gag and a coordinated spit. I jumped as one of them bit the side of my cock and pinched my balls, followed quickly by some evil giggles. The experience was almost like that of visiting a gloryhole. I never could predict what was coming next or who was doing it. I did, however, make sure that I had each of my middle fingers deeply inserted; one in May's tight ass and the other in Andi sopping pussy.

It had to be May who had me in a deepthroat since I heard Andi whisper something, but I couldn't make it out. May giggled with me in her mouth. They were up to something and both of them knew that I loved surprises. They both got up at that point and I thought that I heard a squirt from a lube bottle. Next, I could feel the weight on the bed of what was two legs straddling me and then a hand on my shoulder as whoever it was began to guide themselves lower and lower. Another hand held my cock vertically and steady.

As my cockhead touched flesh, I knew immediately who it was. It was May and her tight ass in a position known as reverse cow girl. Her fleshy bud of an asshole was instantly recognizable and I could feel it just begin to open as she perched atop my cockhead while moving to adjust me to dead center. With the head now almost in, she let her body weight do the rest and I felt her o-ring anus slide down my shaft. With me now in all the way, May squeezed hard around the base and worked me in a circular motion. I just laid there motionless and blindfolded while she gently squeezed and ground. It was both relaxing and stimulating at the same time, almost like a massage. I was on my way, but I could have lasted quite a bit longer with her and her massaging movement. Tonight was our night of gentle lovemaking. Or so I thought.

Although I wanted her to stay and do that all night, May had other plans. She pulled off me and kissed my cheek.

"Now, we're going to make you come. Andi?" May said. Yes, May could have easily made me come, even by only slightly ramping up her gentle lovemaking. Ever the considerate lover, she knew that Andi had gotten rather worked up by listening to our lovemaking through the door but, in any case, she wanted Andi to fuck me to orgasm, hoping also that Andi would get hers in the process.

Tiny Andi climbed on top of me and, while pulling my blindfold off, slid her finger trap pussy down my insanely hard cock and kissed me. She then smacked me hard in the face and said firmly, "Fuck me." The massage was over.

Taking advantage of our physical size differential, I rolled Andi over on her back, the effort causing the last and deepest remnants of May's orgasm to exit my asshole in a rather audible cum fart. Andi giggled, so I smacked her back in the face whereupon she again yelled, "Fuck me!". Needing no further provocation, I pulled her hair, smashed her lips against mine and drill fucked her mercilessly. My balls loudly slapping against her, Andi wrapped her legs firmly around my upper torso while she screamed and wiggled.

It didn't take long for either of us. As soon as I felt the first spurt deep within the tightest of tight pussies, Andi bucked wildly and screamed, "Ohhhhh, Fuuuuck! Fuck me!" Her constricting legs almost preventing me from breathing, she ground her pussy hard against me as she came. The two of us almost felt as if we were one while we held each other tightly, coming down from our highs with each of us still pulsing from our orgasms.

I loosened my grip while she did the same and I kissed her gently on the lips, noticing that the side of her face had reddened. "I'm sorry for smacking you. I really didn't mean to hit you that hard," I said. Andi kissed me back, "Oh, no Rob, that was really hot! I think that sent me over the edge!"

"Fucking Andi," I thought to myself, "She's such a machine." May, who was simply sitting on the bed next to us during the furious fuck, joined us with a collective hug and kiss.

"Rob," May observed, "Your face is a bit red on one side also!"