My Homosexual Journey

Previous chapters;

My homosexual journey Part 1: The First Night

(Straight man has first experience with gay sex and makes decision to change lifestyle.)

-This is a complete fantasy.

-The individuals mentioned are real but I'm using fake names, except for my own.

-To my knowledge Brad and Eric are still together. I was laid off from that company and therefore am no longer privy to the company gossip.

-All persons in the story are obviously over 18 years of age.

-While I feel this story can be enjoyed without reading the previous part, I would encourage you to go back and read

Part 1-The First Night

to get some background.

Part 2-Losing my Anal Virginity

(Joe takes the final plunge and loses his last cherry.)

Recap:

Straight man arrives back home after a night of three-way gay sex and questions his sexuality. While Joe was able to keep from losing his anal cherry Friday night, he basically agreed to have it done by Eric, some time in the near future. He won't go as far as admitting to himself that he's gay, but he will say that he's bisexual. He spent the weekend after that first night researching the effects of anal sex. He got good information and suggestions that made him feel better about the prospect of getting his ass fucked by Eric. But he was still conflicted.

Now on to the story

I ran into Eric at work the next Monday and told him I needed time to mule over my decision and that I would get with him and Brad in a couple of weeks. He agreed and told me to take as much time as I needed.

I realized I had come to a major crossroad in my life. Growing up in a religious household, for as long as I could remember, I was taught that homosexuality was wrong, but it was never visible growing up. I never knew anyone that was openly gay or lesbian. There were a couple of guys in my high school that were thought to have been gay, and that was primarily because they were on the cheerleading team. But their sexuality was never really confirmed as being gay. And I was never confronted with knowing any gay or lesbian people until I started working for the same company that Eric and Brad worked for, and I got to know quite a few people that lived "alternative lifestyles," Brad and Eric being the only gay men that I got to know. For me to decide whether I wanted to be a part of that lifestyle, I had to do some heavy soul searching.

I have never had good luck with women. I had few relationships, but most of the time I was turned down when I asked a woman that I liked out. Michelle really being the only woman to say yes. So maybe dating a woman wasn't in my future, but did I want to be in a homosexual relationship? Maybe. Both Brad and Eric liked me. Brad was the guy that set the first date up and somehow convinced Steve to bring me and later leave me. Yeah, I could blame the alcohol on what happened on their couch, but I agreed with the suggestion to move things to the bedroom and by that time I was sober enough to decide whether to call a cab and go home or stay and join the guys in a threesome. I chose the latter. I admit that I enjoyed the guys' cocks in my mouth, but could I take the next step? I needed more information.

Even though I spent most of Saturday researching anal sex, I needed to talk to professionals. So I called up two friends who were doctors, one specialized in internal medicine, the other was a gastroenterologist. Both of them said there wasn't much chance of internal damage if it was done correctly, like using lubricant. Both stressed the use of protection to avoid the transmission of STIs, but I should be okay. Another person I wanted to talk to was a gay man who I knew from a dialysis clinic. I wanted to ask him how it felt the first time he took a cock in his ass. We met for coffee and he described the pain of the initial penetration which turned to a pleasure that he couldn't describe and it was something I'd have to experience for myself but that it was something that he thought I'd probably enjoy. Armed with the doctors' information and with my friend's encouragement, I felt like I could take the plunge. I didn't really care about what certain friends would think, nor did I care what my parents thought. I knew one set wouldn't like it and would probably disassociate with me, which I wouldn't mind. The other set would probably be more supportive, though unhappy.

With my decision made it was time to call Eric and meet up with him to discuss how we were going to do the act. I called him up and we set up a dinner date at a Carrows restaurant with just the two of us for a Monday night, three weeks after the initial threesome. He wanted to come and pick me up, so I gave him my address.

"So you picked my cock to pop your cherry because it's smaller?" Eric asked me in a low voice, while we were sitting in a booth at the restaurant.

"Because it's thinner, but yes, that's why you get to be the first to fuck my ass. But a part of me picked you because of what you whispered to me when you were fucking Brad. I realized right then that you were right." I answered.

"Brad is bummed that he won't be the one since he's the one that liked you in the first place."

"What about you? Do you like me?" I enquired

"I told you, I wanted your ass that night."

"Well my ass is yours, but what about the rest of me?"

"I'll take as much of you as I can get. Now let's get back to prepping your butt for sex." He started typing on his phone and soon I felt my phone buzz. "I just sent you a link for something called an 'Anal Training Kit.' Before you ask what it is, look at the link. Now when and where do you want to get fucked?"

"I've thought about that. I want to be in a place that I'll be comfortable, the obvious place would be my house. How much bed space would you recommend? I have a twin and it's pretty small."

"Yeah, that's too small." Eric answered. "We want to be in a bed with at least a Full Size mattress, so your place is out. I'd be willing to pay for a motel room."

"Not a motel. That would feel too slutty. We'd need to go to a casino at least."

"Ok. Next question, do you want Brad there?"

"Honestly, I'm not sure. Like you said, it was his idea to have me over for dinner in the first place so I think it would be fair for him to be there."

"And make him watch his boyfriend pop the cherry of the guy who he has a crush on? That's cold. If it's the three of us how would you feel if we were to be at our place?"

"That would work and it gives me an idea. Since my first experience with gay sex was Brad being spit roasted between the two of us why couldn't my first time with anal sex be being spit roasted between the two of you? That way he's still involved in a way. His cock may not be the cock to perform the initial anal penetration but he's still in the bedroom."

"That's not a bad idea. When do you want to bring it up?"

"Maybe we can meet up again at your place Friday night for sex, but still wait on fucking my ass until a later date."

"I'm game for that and I'm certain he will be too. When he got back after taking you home he told me about the uninitiated blow job you gave him and how he you wanted a taste of his cum."

"I did! I looked at it as the final baptism, if you will, that moved me from being straight to being either bi or gay. Even if I didn't want to admit it to myself."

"Wow! I didn't know you felt that way."

"Eric, if it were possible for me to lose my anal cherry to both of you at the same time, I would."

"Ok. Now that the where and how is decided we need to figure out when. Take a look at that link I sent you." I pulled out my phone and looked up that link. Eric continued, "The kit has three butt plugs that increase in size. I think that if you were to pick up the kit from that Adult Toy store this week you can start your anal training this weekend after we're done having sex. We could let Brad put the first plug in. You should be completely stretched out after three months. Brad and I will put the next size plug in after our threesome fuck fest every month. How does that sound?" Eric finished.

"I think that sounds perfect!"

As we finished eating I had another thought. "I have something to tell you, but you need to keep it from Brad."

"What is it?" Eric replied.

"I was hoping that you would have been the one that took me home."

"So was I."

"If you had been the one to take me home and I had asked you inside to take my cherry, even after saying it wasn't going to happen that night, would you have fucked me?"

"I would have been tempted and would have gone inside to see if you were serious. But no, I wouldn't have fucked your ass with my cock."

"I notice that you specifically mentioned not fucking me with your cock. What would you have fucked me with?"

"I would have eaten your ass and tongue fucked you, I may have gone as far as finger fucking you with my thumb and fore finger and maybe added another finger but probably not even that far."

"I so want you to eat my ass."

"I want to, too, but at a later date."

"I'm not so sure I want to wait the three months."

"Wait until you've started that training kit and you've had the middle plug in for a while and we'll see if you're ready for my cock. To be honest, if you've had the third one in and feel comfortable with it in, you're spread wide enough to take Brad's."

"But I committed to you."

"I appreciate that. But I need to get home and I want you to blow me first."

With that we got up and walked to the cashier. As we were walking by, I noticed a few patrons gave us dirty looks. We walked to Eric's car. I now realized why he wanted to pick me up. On the way back to my place we stopped by an adult toy store.

"Go in and show the clerk the link I sent you. They should be able to show you where it's at or even take you to it. Get their advice on which lube to use. This toy will be on me." He finished, handing me a $50 dollar bill. After kissing briefly, I got out and headed inside.

"Good evening." Came a sweet sounding voice. I turned towards the sound a saw a cute petite blonde woman not much older than 25. I thought to myself,

Damn! If I had seen this woman two months ago on the street I would have asked her out and probably fucked her after our first date. Now I

'm going to ask her for a training kit to stretch my ass in preparation to get fucked in the ass by one of my new boyfriends. I walked up to the counter and said, "Hi, I'm looking for an anal training kit. Something like this." I showed her my phone.

"Yes we have that, I'll show you where it's at."

"I need a good lube, also." I added.

"You can't go wrong with a bottle of Anal-Ease. It's in the same area as the training kit." We got to the section and I saw all sorts of different sized dildos. "Here you go." The clerk said handing me a box with three clear plugs and a bottle of the lube. "Was that all you wanted?"

"Yes."

"May I ask you a personal question?"

"Sure."

"Had I not seen you and your boyfriend kissing in the car before you walked in, I wouldn't have thought you were gay."

"To be honest, a month ago, I wouldn't have said I was gay either. In fact if I had seen you on the street I would have asked you out and would have eventually fucked you, if not after the first date. Do you have any experience or advice?"

"Yes I have both. My boyfriend and I had a night of passionate sex and he eventually shoved his dick up my ass."

"Did you guys use any lube?"

"Nope. It was a spur of the moment kind of thing. We've used plenty of that in the few times we've had anal sex since." She pointed to the lube. "How did you turn gay?"

"It's kind of a long story that I can tell you another time if you really want to hear it." I said as she rang up the items.

"I'm actually interested in what turned a handsome straight guy like you into a newly gay man who's about to lose his anal cherry. I close the store at 1 am tonight, it's not usually that busy after 10 if you want to call me. My name is Brittney." She held out her hand.

"Joe." I said taking her hand. "I'll call you later." I paid for the items and left the store and walked the short distance to the car. As I got in Eric was saying, "That took longer than expected."

"The clerk and I got to talking about how a guy like me who, if her and I had met a month ago would have asked her out and may have had wild sex after the date, became a guy who's admittedly gay buying items that are designed to prepare him for anal sex."

"What did you tell her?"

"I said it was a long story that I didn't have time to tell her since you were waiting to take me home. She wants me to call her before the store closes at 1 and tell her the story."

"Will you?"

"I might. She's got a boyfriend, so I think it's intriguing to her. You have to admit, it IS an interesting story." I said.

"I'd like to hear your reasoning sometime, but not tonight. I need to get you home so you can suck this, like you sucked Brad's." As he was saying this he pulled his cock out of his pants and I put my hand around his shaft and started stroking it.*

"Let's go, then. I've wanted a taste of this since we left the restaurant." At this Eric pulled out of the store parking lot. After about 15 minutes Eric pulled up in front of my house.

"I'd like to suck this inside where I have more room, if you wouldn't mind?" I asked still stroking his cock.

"I'd like that." He replied putting his cock away and opening his door. I grabbed my purchase and exited the car, and taking his hand, we walked hand in hand up to my front door. As we walked in, I turned on the light and threw the bag onto my couch. Eric was closing the door as I turned around and pushed him against the door and pulled his head down to mine and kissed him hard. After a few moments he opened his mouth to accept my tongue and after a few more moments of passionate kissing I broke the kiss and backed away and said, "Eric, let me be perfectly clear. I want to have a relationship with just you and forget about Brad. I'd let you fuck my ass right here on the floor in my living room. I'd announce it to my family and all my friends that I am gay and in a relationship with another gay man. If you would just break up with Brad and as soon as he moved out of your house, I'd move in. I want to wake up each morning to you and I sharing a bed."

"Joe, slow down. What if you don't like anal sex? It would make being in a gay relationship kind of boring if it was missing the sex. Let's start out by doing what you and I agreed to at the restaurant. Maybe the opportunity to move on will present itself later down the road."

"You're right. I was going too fast. But I have to be honest with you. Those plugs we bought won't be the first things I've stuck up my ass." I nodded towards the bag on the couch. "I've been experimenting with my fingers, then moved to brush and rounded screwdriver handles since before I moved back to the area. I would do it in the shower when I could use the soap lather as lubricant. I would even simulate the in and out thrusting motion, while I would jerk off, every time shooting a rope of semen that I would rinse down the drain."

"That is interesting to know." My lover replied. "Did you move on to any other toys, like a dildo or vibrator?"

"No." I said downcast. "Wasn't aware there were any. And at the time I didn't want to admit my curiosity to anyone including a random cashier at the sex toy store."

"Once your cherry is popped we'll get you some good dildos or plugs so you can still keep your ass open on the nights that the three of us aren't together." As he finished talking he pulled me in for a short kiss before pushing me to my knees. Knowing what he wanted, I opened his pants and fished out his cock which was semi hard. I took his cock into my mouth and started sucking and immediately felt the shaft grow in my mouth. Once it had grown to its full size I removed it from my mouth and lifted it to give me better access to his balls. I sucked each one into my mouth and swirled my tongue around them. Eric moaned, "That feels so good Joe! One of these days you'll have to try taking the whole sack in your mouth." I continued my menstruations for another minute before allowing the testicle to slip out of my mouth with a "Pop!" I licked the underside up to the head and wrapping my lips around the shaft proceeded to bob up and down Eric's smooth shaft wrapping my tongue around it with each stroke.

After about ten minutes, Eric placed his hands on the sides of my head and began thrusting in and out of my mouth, after another five minutes of hard face fucking, he shot multiple streams of cum down my throat. Not giving me much time to swallow, he pulled me up into a passionate kiss which didn't last long before he broke the kiss and said, "Go over to your couch and pull your pants down and get down on your knees and lean over and rest your elbows on the cushion. It's time for you to take your first step towards losing your anal cherry." I immediately obeyed and made my way on my knees to the sofa and undoing my belt and button I pulled my pants down to my knees and leaned on the cushion. Eric was behind me. I felt a hard "SMACK," against my ass that echoed in my small living room. He squeezed each cheek before smacking them again. I felt him spread the cheeks apart revealing my puckered rosebud and said "I've waited a month to see this." Then I felt his tongue lick up my crack from my balls to my back and back down. On each pass he would stop at my hole and lick around the rim. After two or three passes I felt him stop and surround my hole with his lips, then I felt him shove his warm stiff tongue into my sphincter. I dropped my head onto the cushion. For a minute or so, Eric tongue fucked me, before moving his mouth and after slapping my ass again he sat up. I turned my head to the side and said, "That felt so fucking good! I can't wait for what's next." I didn't have to wait long. I felt a large drop of saliva land on my back and Eric use his thumb to spread it around my hole before shoving the digit past my barrier and through my rosebud. I sucked in a breath of air and instinctively clinched my anal muscles.

"Relax. Don't clinch your ass." My lover said as he continued to rub the inside of my ass. I then heard him rummage around in the shopping bag, I turned my head and saw him pull out the bottle of lube.

"I thought we were going to wait." I said.

"It's for my fingers. If you don't like a couple of fingers fucking your ass then you're sure as fuck not going to like my cock fucking you."

"I guess you're right." I conceded. I heard him remove the protective wrapping and then heard the cap pop open and felt the cool liquid flow onto my ass and him use a finger to spread it around before sliding it in my ass.

"How's that feel?"

"Good. Some pressure when it went in but now it feels great."

"Good. I'm going to start thrusting in and out now. Breath out when I'm pushing in. If it becomes too uncomfortable let me know." I nodded and felt him start to thrust in and out. I let out a moan of pleasure.

"Ready for another finger?" he asked.

"Fuck yeah!" I exclaimed. I felt some more lube drop onto my crack and him spread it around, then felt a second finger join the first. I felt Eric thrust in and out, but this time he added a twisting motion each time he pushed in.

"One more!" I shouted. I felt a large amount of the lube drop onto my ass and a third finger was added. I was being opened up larger than any brush or screwdriver handle ever had. "Yes Eric, finger fuck me!" And he continued fucking me with three fingers for a few minutes before it all stopped. And even more lube was poured onto my ass and felt a heavy piece of flesh drop into the puddle of lube. I felt him spread the lube around with his cock head before pushing it past my barrier.