Matchmaker, Matchmaker

A bit about myself: I'm the youngest of four children, Montgomery by paper but Moe to friends and family. My mom lost her husband and our father when I was fifteen; Dad provided well, even after death. With members in his family passing at an early age, he made sure to carry a good amount of insurance just in case, and doing so allowed Mom to continue to put us kids first as she always did. We were some lucky ones, a stay-at-home Mom and a free education.

So here I am, returning home from college with a degree in hand. Since I left, Mom's focus has turned more to her grandchildren, and since leaving and coming back, she already has four of them and one more on the way. One of the things on my to-do list when I get back is to sit down with Mom and inform her not to plan on getting any from me. I dabbled in bisexuality during my first two years away, but since it has been all guys only for me. Not that I don't like girls, I just like cock much better.

But as things tend to do, things got more complicated when I got back--or, better said, fast-paced. I never found the opportunity to speak with Mom, and now she is setting me up with a friend's daughter. "Oh, she is so sweet. I know you'll love her." Mom babbled. The one thing I got from Mom was the inability to say no, so I caved in. "Great, I will call Karen and tell her you are interested in Jamie."

"Mom, I said I would go out with her, so don't get too excited," I told her. Mom kissed me on the cheek, telling me how much I would love her. I thought to myself, what kind of mess did I get myself into? Before I could leave the room, Mom was on the phone with Karen, and it seemed Jamie was convinced by her Mom at the same time. Well, at least our Moms will have a good time.

I looked at the date as a chore and just wanted to finish it. Having no fuck buddies in town, I wanted to find one soon, as my hand can only take so much. We met at a local bar, one that serves food. It was new to me, having changed owners and names since I left. So where is the girl in the red top? Then I spot her sitting at the bar, long and lean, plus almost as tall as me. "Jamie? (tapping her shoulder)

"Hi, you must be Montgomery."

"Just Moe, please."

"Well, hell, Moe, my Mom didn't lie. You are good-looking." (her eyes up and down my body.) "Well?"

"Oh, yeah. You're looking good too, I mean very pretty."

"So what, a seven out of ten?" she asked. I didn't respond but thought if only you had a dick.

We might seem doomed at the start, but after a couple of drinks, we actually got along. Was I in love? No, and I won't be changing teams again. But if I were to, she was just my type. We danced some, ate, then danced and drank some more.

As it was getting late, I said, "Well, maybe we should call it a night."

Looking at her watch, she said, "Oh, it is, but can you do me a favor?" She went on to tell me how it would be great if I could go home with her. She lives next door to her Mom, and she will be watching. We don't have to do anything. I'll even sleep on the couch. I don't want to hear it from my mom in the morning. "Then I will make something up later."

"Sure, that would help to get my mom off my back, too," I confessed. (laughing) "And you do not have to sleep on the couch; just keep your hands to yourself."

(Laughing in return) "I think I can do that."

When we arrived, she excused herself to get into something more comfortable and returned in a lovely robe. Over her arm was a pair of sweats, and she offered them to me. Since I was staying, I was happy to get them.

We sat on the couch talking, and she noticed me moving my neck around a lot. "Are you okay?"

"Yeah, just a neck injury I got wrestling."

"Well, I hope you pegged him, I mean pinned him."

I thought, "Shit, she figured me out. I hope she doesn't spill the beans, at least not until I talk with my Mom." But then she started to rub my sore neck, it not only felt great, but I began to regret my stance as surely pussy isn't a bad second. But she stopped saying it was time for bed and asked if I would join her.

"In a minute, but is there any way I could use your shower?"

"Oh, sorry. Of course, it's right through there." (pointing)

I showered, finding my release while doing so, and when I joined her, she was fast asleep.

I woke and forgot where I was, stroking my morning woody. I gazed at Jamie with little desire to stop when it dawned on me. I was still sleeping, but what the hell was that? Peeling the covers back, she found she was sporting morning wood, too. I left the covers back, looking at her nice cock while I stroked mine. Then, as I was about to pop, I heard. "You can suck it if you want to."

(Startled) "Oh shit, sorry."

"Don't be; just do a good job." She remarked.

With great interest and her permission, I went straight to work. It was like her cock was made for me, the perfect size and a slight bend which caused no gag reflex taking her balls deep. Her loud moans let me know she was into it, too. Then she rang out how I better stop, or she was going to cum. In response, I doubled my efforts and added a finger in her ass.

She arched her back, so I prepared myself. And just then came my salty treat, which I gobbled down. Still horny, I spun her over, and after tonguing her ass, I pressed the head of my cock against her hot hole. Moaning as she pushed into it, inch by inch until my balls smashed against her.

She had a death grip on my cock, causing me to spill myself far quicker than I hoped to. We kissed, holding each other for a few minutes. Then I spoke up, saying how I had no clue. She explained how she knew early on that she wanted in her right body and how understanding parents came to her aid. And it surely worked in her case, all but a woman. She went to kiss me again, but I rebuffed her. "What's the matter?" she asked.

"Well, to tell you the truth, I'm eighty percent Bottom. So I do not want to mislead you."

(She laughed) "Well, I'm ninety percent a Top." Then she kissed me, this time heartily welcomed.

There were many great things from our meeting, including that we didn't have to lie to our mothers. About three months into our relationship, I needed to tell my Mom that I was moving out and into Jamie's place. I knew she would be very pleased to hear that, so I figured I would also tell her how she can't count on me to add to her grandbaby list.

I went to do exactly that, but when I told her I was moving in with Jamie, she hugged me and whispered, "You boys can always adopt." We added two to her list, totaling nine. Jamie, I, and our Moms couldn't be happier.