Levels of Happiness

Author's note: This story is correctly labeled in the crossdressers/transgender category. Please be patient.

I love my boyfriend Brian and I know that he loves me.

Let me start with a little bit of background before I start my story.

Since about the start of my sophomore year in high-school I began having feelings that I might be gay and considered coming out to family and friends. I changed my mind after watching news on the television and reading the newspaper. There was so much rampant violence, teasing, and hate mongering towards gay people that I decided to keep my feelings a secret.

The college I attended was several states away from where I grew up and I felt more free than I had ever had in my life. You get a bunch of horny young people full of energy and hormones. You put them together away from home and out from under the thumb of their parents and they start experimenting.

A month into my first year, I lost my virginity to a woman. Oh boy. I thought that it was supposed to be a life changing experience. It was, but not in the way society and culture portrayed it. I orgasmed into a condom when I was inside of her and I instantly felt regret and shame. This was not what I wanted and not the kind of person I was attracted to.

A month later, I lost my real virginity to a man. Holy shit! Yes! This is what I was looking for. It was an amazing, absolutely incredible experience. His cock smelled and tasted divine. The pounding he gave my ass was so awesome that I still dream about it today.

This is it. This is who I am. I came out as gay and I was happy and proud. To hell with what others think about me. You only live once.

After graduating college, Brian and I both moved back to our home city and reconnected. We had lost touch when we went to different colleges after high-school and ran into each other while getting gas. We had been best friends since middle school so it was no surprise when we became roommates. Brian was straight and didn't care that I was gay. That is the sign of a true friendship.

About a year after we started rooming together, Brian came home from a date angry and frustrated. Over several beers and half a bottle of tequila he told me how his girlfriend dumped him for another guy. He had tried for several weeks to get her into his bed and she had been fucking some other guy the entire time.

Brian was sitting on the couch, head slumped back, facing the ceiling eyes closed, slurring his words as he described her curves and what he wanted to do to her.

I felt so bad for my friend as I listened to his story of heartbreak. By this time I was also quite tipsy. Not as drunk as Brian, but feeling no pain nonetheless. I was also horny as it had been some time since I had gotten any dick.

Between the alcohol and the dry spell I wasn't thinking straight. Haha! Thats funny. I am gay. I never think straight. Anyway, I really wasn't listening to him talk. I mean I was, but not really. My attention was more focused on the growing tent in his pants. Before I could think about it, I said in a very feminine voice, "I could take care of that for you baby," as I reached for and gently massaged the hard lump.

"Wha..?" he asked, barely opening his eyes, not moving a muscle.

"I can make you feel good," I replied, retaining my feminine voice as I unbuckled and unzipped his pants. Moving to my knees between his legs, I fought with no help from him, to pull his pants and boxers down.

"Whatcha doin?" Brian asked in a slow drunken drawl.

I said nothing as I took the hard member into my mouth.

"No. Stop. I am not gay," as he pushed me away.

"Nobody said you were," as I stroked him with a soft hand.

"Aaaarg!" he screamed out in agonized frustration.

"Its just that you feel so good and its been so long!" he complained with his head still back, afraid to look at me.

I stayed quiet as I continued the handjob. It was his move and I needed him to give me the ok to continue.

"Aw fuck it!" he cried out. "I don't give a shit. I am drunk and horneeee!"

The last word out of his mouth turned into a moan as I engulfed his big dick again. This time it went all the way down my throat. A free hand massaged his full hairy balls.

Even though Brian and I were best friends and we expressed our love for each other, somehow I never thought about him as a potential lover. Until tonight. As I sucked his cock I thought about how handsome he is, what a great body he has, and how he has been such a wonderful friend when everyone else turned their back on me.

I wanted to please him so badly and in a way maybe even repay him the kindness he has shown me. From all my experience I knew that I was really good at sucking dick and I really enjoyed it.

His dick tasted so good and was the perfect size for me. Circumcised, big and thick without being huge, not too mention these gorgeous low hanging balls. What an amazing specimen of studly testosterone man. This was one dick I would really like to suck again. I thought that in order to do that, I knew that I would have to give him the best be all, end all, mind bending, holy shit orgasms ever.

My own dick got super hard at that thought as I went to work.

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After swallowing his delicious load some 30 minutes later I retrieved a warm washcloth and cleaned him up.

"Come, let's get you to bed," as I picked him up off the couch. He stood, swaying slightly, as I pulled up his boxers. I wrapped an arm around his waist and helped him stagger off to his bedroom.

"That was awesome," he slurred out as I unbuttoned and removed his dress shirt. "Thanks buddy."

After tucking him into bed, my fingers lightly grazed the impression of his soft cock under the covers.

"Goodnight Brian," I smiled.

"Goo....nigh..." he barely made out before his breathing became shallow. I heard it morph into a soft snore as I closed the door behind me.

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As was every Saturday morning, I got up early and made the two of us brunch. Sometimes it was just me if Brian had a hot date from the night before and didn't come home. If his girl spent the night, I would leave the fixings for them and eat mine in my room.

Fear crept through my mind when Brian didn't emerge from his bedroom lured by the fragrance of fresh coffee and bacon. Did I fuck up our friendship just because I felt sorry for him and wanted to make him feel better? Was he mad? Was he embarrassed that his gay friend sucked his dick? Was he wrestling with the thought that he might be gay since he enjoyed it so much? Was he so drunk that he even remembered it?

These thoughts were running through my head as Brian walked into the kitchen. Usually, when he came out for brunch, he would be wearing boxers and t-shirt, hair a mess, groaning for coffee while still half asleep.

This morning, however, he smelled great, and was freshly showered and shaved. Instead of the boxers, he had on khaki pants and a nice pullover collared shirt. Just like me. I am a pudgy, goofy looking dork, but I try to make up for it by always appearing nice and neat.

"Good morning," I softly said.

"Good morning," he quietly replied.

We sat down to our meal in an uncomfortable silence, not being able to look at each other.

I guess that I was fidgeting too much when Brian said "Stop" as he placed a hand on my arm.

"What?" I asked looking at him, startled by his word.

"Stop worrying, you and I are grown men and you didn't force anything on me. I really enjoyed it and I am not mad."

I smiled warmly. "Good. I was happy doing it and I wanted to make you feel better after your breakup."

He sighed. "I thought that she could have been the one. That's why it hurt so bad."

I chewed on a piece of bacon while I let him wallow a bit.

"So why did you wash up and get dressed? Are you heading out?"

"No. I don't have any plans for today. You always look so nice for brunch I thought that why shouldn't I?"

"Thank you. You do look very nice this morning," I smiled

We ate in silence for a few minutes before Brian spoke again. "You know, even though I was shit faced drunk last night, I know that was a super amazing blowjob."

"Really? I was that good?"

I knew that I was, I just wanted to stoke his ego a bit and keep him comfortable talking about it.

"Yeah probably," then, pausing a moment to collect his thoughts. "No, not probably, that was definitely the best blowjob I have ever received."

"Thank you. I loved sucking your cock."

Throwing caution to the wind, I added, "I would be more than happy to do it again."

Brian laughed, "I just might take you up on that offer sometime."

That sometime ended up being later that night.

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The blowjobs started slowly from twice a week to almost every night. I wasn't complaining, I really enjoyed sucking his dick and he obviolesly enjoyed it too. This led to him fucking me in the ass. It

was my suggestion and he was more than eager to oblige.

After he orgasmed, I would bid him a goodnight and head off to my bedroom where I would jerk off while I relived the escapade of the night. Sometimes I would cum into my hand and lick it up, pretending that I was getting another load from Brian. Other times, I would fuck my sloppy hole with a dildo the same size as Brian cumming into the sheets, and falling asleep in the wet spot on purpose. Happy and satisfied.

After one particularly fantastic ass fuck, I said my usual goodnight as I picked up my clothes in preparation to leave.

Brian asked, "What do you do when you go to your room?"

"I usually jerk off reliving the night."

"You are not satisfied with what we do?" Brian gently asked.

"I am satisfied. I totally love getting you off. I just need my release too."

"I'm sorry. I didn't realize that I was being so selfish. Of course you have your needs too."

" I take care of them just fine."

"I umm...would like to umm...help you ummm...get off too."

Brian was really stumbling through his words. Probably happy that I couldn't see his face in the dim light.

"What do you want to do to help me?"

"I...ummm...I'm not sure..."

"Tell you what. Next time we fool around, we will take it slowly and we will only go as far as what you are comfortable with."

"Ok," he seemed relieved at this idea, as I could just barely see a hint of a smile.

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Two days later, I was in the shower when Brian walked into the bathroom.

°Hey," he said, announcing his arrival.

Startled, I poked my head out and smiled, "Hey!"

I was surprised to see him in my bathroom as each of us had our own bathroom. I was doubly surprised that he was wearing just a towel around his waist.

"Can I join you?"

"Yeah sure," I said as casually as I could. Internally, my heart was leaping for joy as I opened the curtain to let him in. All of our encounters thus far had been in a darkened room at night and this was just after noon.

Brian shed his towel, laying it on the toilet as he stepped naked into the shower with me. The close proximity of the small stall made touching each other an unavoidable necessity. Not that I was going to avoid touching him, quite the opposite.

"How about I wash you?" I suggested.

"Ok."

We moved around so he could get under the water stream. My cock began to harden while I watched the water cascade down his hot body. His time in the gym was certainly paying off. Brian was fit and lean, muscular without being super-sized bodybuilder big. I watched in awe as he wetted down his hair. Biceps and chest flexing in rhythm with each other.

Squeezing some body wash onto a scrubby, in addition to using my hand, I slowly and gently washed the bare skin. I became hard as a rock as my fingers made their way down south, savoring his marvelous physique.

Grasping his hard cock in a soapy hand I began to stroke.

"Damm that feels good," Brian moaned out, "I am supposed to make you feel good too."

"You do make me feel good," as I pressed our dicks together and stroked with both hands.

Brian looked down and smiled. His thick 8 inches much more masculine than my 6. "I am really enjoying this, never thought I would've."

"Just you wait," I giggled. "There is a whole new world out there for you."

" I think that I would like to venture more, just as long as that world stays within confines of this house and between you and me. Now turn around and let me please you."

I released our hold and turned.

"As much as I want your big dick in my ass please don't. Soap can cause uncomfortable burning inside."

"No worries. I did that with a girl once and she was sore all day long."

"All day? I heard that it only lasts about an hour or so."

"She was emotionally sore at me too. Seems like she was always complaining about something. Unlike you,Terry. You have always been so good to me."

Brian squeezed out some more soap, applying it generously to his cock and my ass cheeks. Then, reaching around, he grabbed ahold of my dick as he nestled deep into the crack of my ass.

"You are so smooth and soft." Brian softly said.

"I know, I am sorry. I need to go work out like you do."

"I am not complaining."

Turning my head around, I smiled up at him. "You are a good man, Brian, but you better stop."

"Why? Isn't this what you wanted?"

"Oh my god yes! With your dick on my ass, your bristly cheeks on my neck, and your hand on my dick I am about to cum way too soon!"

Brian slowed down. "How long does it for you to recover and get it up again?"

"Oh, with the right stimulation about an hour."

"I can wait an hour," as he picked up pace.

"OH FUUUUCK!" I screamed out as I sprayed batter all over the shower wall.

Suddenly weak from the intense orgasm, I began to collapse. Brian quickly caught me in his strong arms.

"Good?" he asked.

"Um, yeah," I barely made out as I came down from the intensity of the orgasm.

After a minute or so, I found my legs and turned around to face my lover. Looking upward into his incredibly handsome brown eyes I thought that we were the perfect height for each other. Me being the submissive 5' 6", and Brian a masculine dominant 5'10".

"Thank you. That was incredibly awesome," as I toyed with the light curly hair on his chest.

"I am happy to make you happy."

Brian and I looked into each others eyes, trying to figure out each others emotions as we allowed the water to wash away the soap. We had been best friends since an early age, then sex buddies, then this.

This was something new. Were we really going to cross that threshold? I knew that I wanted to kiss him, but I was deathly afraid of scaring him away. Would it be too much too soon?

Before we could answer those questions, the water begin running cold and I stepped out. Trying to hide a look of disappointment on my face I kept my back turned as I dried off.

Brian turned off the flow and grabbed his towel. "Hey, I -"

"Its ok," I bravely smiled.

"No its not ok. Come here," as he spun me around to face him. Wrapping his beefy arms around my body, he pulled me into a passionate kiss. We both dropped our towels as our tongues fought in our hunger for each other.

Breaking for air, we were both panting from the burst of energy.

"I love you Terry," Brian smiled in adoration. "You have always been so good to me. You have been there so selflessly always giving and never taking. There to pick me up through breakup after heartbreaking breakup. You and I get along so fabulously well. We have the same sense of humor, the same love of movies, music, and so much more."

Then, after pausing as if to collect his thoughts, "Not to mention some of the most incredible sex I have ever had. You are the one I should have been chasing instead of all those skirts."

"I love you too Brian," as we kissed again.

"You know I could wear a skirt for you," I grinned.

Brian and I got a good laugh in and we forgot about the comment as he led me off to his bedroom.

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From that day on, we slept together in the same bed and neither of us dated anyone else. The sex increased in intensity and passion. Brian was up for more new things all the time. Sometimes it was my ideas. Some of it was his.

It was his idea to give me head. As a complete novice, he wasn't too bad his first time and he didn't like me cumming in his mouth so we didn't do that again. He didn't suck my dick much. I knew that he did it mostly because what guy doesn't like his dick sucked and he wanted me be happy.

It was also his idea for me to fuck him in the ass. He was curious to know why I loved to so much. Yeah, that is a never again experience. I am 100% bottom and he is 100% top. We are just built that way and I give him props for trying.

I know that he loves me and wants to express that love in different public situations. We talked at great lengths about coming out as a couple. He just couldn't do it and I have way too much respect to force him to do it.

Its ok. It really is. It takes an incredible amount of courage to come out as gay. It is a cruel world out there. Me? I absolutely had to, there was no other way. It was eating me up inside and I have never looked back.

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I think that it was about a year after our first kiss that I first sensed some uneasiness in Brian. Did he need something more? Someone different? Before he and I started fooling around with each other the longest relationship he had been in was 6 months and now we were exclusive for more than a year. I casually asked him about it without prying to much, and he reassured me that we were good to go.

i think that Brian feared uncomfortable questions about his sexuality from friends and co-workers. Maybe he was already getting those questions asked. Why doesn't he talk about his latest girlfriend? Why is Terry always around?

Bit by bit, I sensed a breakup and I didn't know what to do about it. I was frustrated and I think the added tension was tearing us apart even faster.

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I have the great fortune of working from home and I never go into an office. My work alows me to write my own schedule so I have alot of free time if I get a project done early or I will work late into the night on a tight deadline.

One day I was bored on a super easy job and needed a break before I made any mistakes due to a wandering mind. Brian and I talked about how even though our sex lives were fantastically fulfilling, sometimes we needed to literally take matters into our own hands. So I decided to do just that.

Online porn was exactly what I needed to get off. The usual go to sites for some reason just wasn't doing it. Horny and frustrated, I started clicking on anything in hopes of finding something. Bareback, fisting, outdoors in public, orgies, gloryhole. I even tried piss play. Definitely no. Good for you if that's what you like. Just not my thing.

About to give up, I recklessly clicked on one more thumbnail without reading the description. The scene that came up was a beautiful curvaceous transgender woman with a medium sized dick getting fucked by this hot stud of a man.

"Oh shit!" I said out loud, this was not my go to at all. Holy hell was this hot! My cock sprang to life as I watched the clip and I jerked off with lust filled craziness as I watched the two go at it.

I imagined that it was me with the long hair, big breasts and makeup being fucked by the guy. Her dick was swinging around as the man slammed in and out without abandon. At first, they were fucking dog style until they changed position and she was on her back. Mounting her again, he grabbed her shaft as he stroked her ass. All three of us came at the time. What a hot fuck!

Before the clip ended, as I was wiping up my own cum, the couple settled into a comfy cuddle as they kissed. Awe! How sweet I gushed as the scene faded away.

Just then, an idea popped into my head. After a couple of hours of clicking around various sites on the internet I had a plan. I was madly in love with Brian and I was going to do whatever it takes to keep him.