tagTransgender & CrossdressersMy Two Lovers Ch. 01

My Two Lovers Ch. 01


Leland shuddered as I twisted my fingers inside him. This was supposed to be one of our twice-a-month weekends together, but something had come up and he had to go back home in an hour.

So no time for Lolita today. Or rather, I didn't want to take the risk, even though he was. I wanted us to play it safe, just for a couple of years, until he could be free and we could think about a life together.

He lay face down, in what I had begun to think of as a standard milking position for him: ass up, feet close together, with his penis pulled back through them, so I could fist him while I ate him out.

It was a shame: a lot of effort and planning went into our get-togethers, and it hurt to see it go to waste. It hurt more to see his efforts go to waste. I had gifted him strawberry scented astroglide the last time we met, and he had taken the hint, working it in after he douched himself. It made rimming him even more fun.

His anus wasn't the prettiest one; he was a couple of years older than me and age had taken its toll, but he took good care of it, with bleach and cream, and it was a joy to behold as it opened up for me.

If you aren't rimming in your relationship, you're really missing out. It's bad enough a lot of people haven't discovered how erogenous their asshole is, don't further deprive them of this lovely experience.

When you're milking though, you have to have a firm grip on your partner's cock, with a sort of rippling motion going down.

"That's it baby, come for me," I coaxed him, licking his balls and drawing them in. His balls didn't hang low like mine, but stayed in a tight sac that I could squeeze gently and fit entirely in my mouth, and roll around a bit.

I stopped fisting and laid it on my palm, feeling it move. We had done this so many times that I could feel his heartbeat through his dick, feel how close he was getting. And he was close. I resumed tonguing his hole, and started running my finger tips along his length.

He grunted into the pillow and immediately started spurting onto my hand. I smiled at being able to bring him off with a sense of control, at our level of comfort with each other. Normally we would share his cum, but today I licked it and then went to wash the rest off.

When I returned, he was sitting forlornly at the edge. "At least let me blow you?" I shook my head and drew him up to stand, silently initiating one of our "couple's time out" sequences.

We kissed, and we each held the others cock in one hands, not too hard, but not too soft either. I slipped my hands around his globes and slipped one finger in, and he brought a hand to my face.

It was a way of saying: I'm holding you in my hands, I'm feeling you, I'm supporting you. I can sense and fulfill your needs, I cannot hide my feelings from you, nor you from me.

"Your cock is my cock, your life is my life, your seed is my seed", he whispered to me, and I whispered back, "your pussy is my pussy."

This was a sort of personal manifesto we had shared during the early days we slowly realized the two of us wanted to belong to each other for a long time. After it, we always felt like everything was going to be okay.

"Alright, just ... real quick, come over here." I sat down on the edge of the bed, and pulled him on to my lap. I brought our cocks together and rubbed us, and he held on to my shoulders as he threw his head back. Precum flowed from both of us, and I slicked us up, then slowly pushed him, lined him up, and sat him down.

I didn't want to nut in him today, so I tried my best to focus elsewhere. He wasn't having it though, and tightened around me. "Don't! I can't!"

"Yes you can. Do it."

"I don't want you to be leaking, baby."

"Don't worry about it. I love you, I'm not going back empty. Is that what you want?"

"Of course not, you know how much I like being in you, but ..."

"It's okay, don't worry about it. Look at me. Relax. Let it go."

We were both vibrating with excitement now, his own cock rigid between our bellies. I scrunched my face up, and he brought me to his neck, whispering encouragement.

"I want to feel you blow, baby. Breed me. Stick your juice inside me. I want to feel it flowing within, I want to carry it with me, I want to soak it up."

I exploded, gripping him tightly as I shivered with each spurt. We remained attached, as he stroked my hair.

"Don't worry baby, it'll be alright. Don't worry."

He leaned over and picked up a small plug, and brought it between our lips so we could kiss its tip. We carefully maneuvered so he was on his back, and I pushed up, rolling him upwards, until his hole was facing up.

I held his cheeks apart, as he carefully placed the plug next to my shrinking cock, and pushed it into place as I withdrew. I licked around it, making sure there was nothing that would leak downwards later.

"Well, if you're going to wear that, you might as well wear this too," I picked out the pair of panties I had got this week (I made it a habit to buy some one small item every time we met — it made both of us happy), and placed his feet into it.

He smiled and slipped it on, then got up and got dressed. "I suppose you'll be needing additional care tonight?" he frowned. I looked away for a moment, since I knew he was right, and I knew he knew he was right.

"Darling, you know you have nothing to worry about." I saw that he had forgotten to tie his hair back, into the pony tail that he customarily wore, and let down only for me, and tied it into place for him. "Now go, and take care, and ... I'll see Lolita next week. I have something special planned for her."

I put my robe on, and I paced the room for a couple of minutes, but it was a foregone conclusion. I texted Brandon, "booty call", and got a smiley in return, along with "on my way."

I fixed a couple of drinks, and though I felt guilty at using the stuff I had intended for Lolita with Brenda, went through with it anyway, setting out the bath, and the candles in my room.

I scrolled through our previous messages, finding a pic he'd sent me a couple of days ago, on all fours, panties pulled down just a quarter inch below his dangling cock, showing off his smooth hole.

I flipped up to the previous pic, a selfie he'd taken when I was balls deep and in the act of pulling out, the angle making it look like his cock continued where mine left off, as if I had punched a hole through him and come out the other side.

I was sitting near the window when the bell rang, and Brendan popped in, his usual perky self. He hugged me tight and gave me a peck on the cheek.

"What's the matter, daddy, the wife isn't enough any more? She got too old? Left you?"

"Now now, be nice," I said, with a playful pat on his bottom as he turned and dropped his bag on a chair, "how's school?"

"Good. Had something to submit after the weekend, but I'm mostly done already," he took his jacket and shirt off, and stretched his arms out, "so I'm all yours for a day."

I twitched. He knew it. With Leland, he knew that the slightest turn of her hands on my balls affected me, and had complete control that way. With Brandon, he knew that the slightest twirl of his smooth, sleek body affected me, and had complete control that way.

He stayed stretched, waiting for me. I relented, and fell to my feet, undoing his trousers, pulling them down. Brandon always wore panties, but unlike Leland, liked buying them on his own. The young and their silly fashion sense.

I rolled the top of his panties down, freeing him. His lovely little cock flopped down, and I kissed it. It fit in my hand, along with his balls, and I held them now as I stood up, lightly squeezing them to make him jump.

There is a spectrum of love that everyone needs, and for me, cliche as it may sound, I needed a wife, and I needed a mistress. They were different, they loved me differently, I loved them differently, but I wasn't complete without both of them.

With Lolita, there was always a certain kind of reciprocity, or lines that I couldn't ask her to cross; with Brenda, I could make demands, ask her what I wanted, more forcefully, more freely, and (I hate to admit it) often more honestly.

"Yes," I nodded, raising his chin with the other hand, "mine." I kissed him deeply, and he parted my robe. I lifted his hands, and kissing them, brought them to my dick.

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