Hampton Heights

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Guy experiments with a friend who then sets him up with a TG.
15.6k words
4.82
34.3k
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Part 1 of the 2 part series

Updated 06/11/2023
Created 10/05/2021
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Deeplust
Deeplust
719 Followers

***To the haters...Fuck you, dont read my stories.. If you dont like my writing...dont read it and dont complain....its free. You want better...PAY ME.***

To my fans...I have more to this story if it is good

I moved into Hampton Heights when I got my first big payday. I decided to work with my father at his construction company and then after a fight, I was on my own with my own customers. Things were tough for a few years but I stuck it out. I like to think of it as paying my dues. Working sixteen-hour days, nobody ever said that I was taking the easy road and I wanted a nice place to show that I had achieved something.

Hampton Heights was an exclusive neighborhood that consisted of townhouses in the ultra-tight knit part of the county. I was thirty and living by myself and enjoyed the peace and quiet of the gated community. The parties were always big and everyone that lived there was making enough money that they did not worry about money. The only issue with the community is that everyone was a snob.

Owning my own business afforded me the opportunity to do and say what I want and even thought I wanted to keep the peace; I still didn't give a shit about what I said. I kept my mouth shut in the neighborhood though, not because I choose to but because I was just not around enough of the people that they heard what I had to say.

With my business taking off I decided to lay back for a time and enjoy life. I had girl friends to occupy my time, but I never really found one that I wanted to live with or stay around for more than a month. I was not using them just for sex but would tell them I am not looking for a relationship. I still recall telling my last girlfriend Tiffany that I did not want to be her boyfriend and that I was not the guy she wanted to stay with.

The parties at Hampton Heights were all done by the guys who wanted to watch football on Saturday and drink beer with no nagging wives around. Since I was the only bachelor that watched college football, my place became the Mecca of Saturday beer and football. This did not end with football and every Saturday my place became the social hub of the neighborhood even when there were no games to watch.

Now the wives would stop by and check up on their husbands, but we never had any bad stuff other than rude talk and beer. I still heard the girls talk about me being a male pig with a constant string of girlfriends and I even had Johns' wife offer me sex thinking I was some sort of sex object.

Now I kept my body in shape since I was in construction and by the time I stepped back at thirty, I had my nice six pack abs and arm muscles that went with it. I know some of the girls talked about me and what I looked like nude, but I had a thing about cheating and would never cross the line with my friend's wife.

Rick moved into Hampton Heights and instantly became the talk of the neighborhood. He was about my age with a slender build, but there was no denying his homosexuality when he was in the room. His voice had a flair to it and his movements were feminine. He was not flaming as some would say, but he was not hiding it either.

The neighborhood was in an uproar about a "homo" moving in as some of the girls said. The ultra-wealthy area were also very conservative when it came to sexuality. They were very religious and to most of them, Rick was the devil. The housing complex had a committee and the right to decline anyone that applied to live there. The lawyers were quite good about making the rules and they could deny anyone with no reason given for why they were being denied.

To me, I didn't give a shit and found that the main person behind it was Samantha Graves. Her husband was a tool and never hung out with the rest of the guys anyway. She was a bitch and most people hated her for a multitude of reasons. I decided to tell the guys that it would piss her off if we all said yes to Rick moving in just to take a shot at Samantha and her husband.

The guys instantly agreed and even said they had no real issue with Rick anyway. We all decided to tell Samantha we would vote with her and then vote against her when it was brought to the real vote. It was a big formal meeting and I saw the look in Rick's eyes that he knew he was not going to move in. He had no lawyer and even if he did the housing committee was a private entity with no recourse for people to sue.

Samantha gave her speech about morals and how some people will not fit into the fabric of Hampton Heights. We all nodded and looking like willing subjects to her. I saw her cocky smile and knew it was going to be the biggest shock to her that we were not going to vote against it. I then later found out that even the ultra-religious people didn't really give a shit about Rick being gay and were more worried that Samantha would use her influence in church to oust people from certain positions. I laughed when I found out later that it was only Samantha that did not want Rick and even the pastor cast his vote for him in without him being knowing about our secret meeting.

The vote was read and I just saw smiled around the room. I saw Rick was utterly speechless and everyone seemed genuine about welcoming him into the community. The wind was ripped from Samantha's sails and I knew she was going to try and get even. I could not be happier that the good prevailed and even offered an invite to Rick to watch Saturday football with us.

After the football season it was the basketball tournament. After basketball it was baseball or just hanging out. Rick fit in with the guys like a glove. He was our gay friend that offered fashion and girl advice. He was still very openly gay but he never flaunted his gay pride or made it seem that we had to change. We never made it seem that he had to change either.

Rick was a stock broker and had a few boyfriends here and there but nothing very permanent. He brought only a few of them around us and they just didn't seem to fit in. It was not us that rocked the boat either as he said it and once, he even dumped a guy for talking trash about us.

I knew Rick loved that we stuck up for him and we even told him that if Samantha had her way after the fact that we would all move out in protest with him. I knew a few times he almost broke down in tears as he said that we were like an extended family to him and he wasn't our gay friend, but just our friend.

***

I lifted up the case of beer moving it inside as everyone had left except of Rick who was helping me clean up. With a grimace of pain, I moaned out. "Fucckkk!"

"You hurt your back?" Rick asked.

"Yea. Fuck...I hate when it goes out." I replied knowing that one of the reasons for my half retirement was my back giving out.

"Lay down. Let me get you some ice." Rick replied as he walked over to the cooler with a hand towel to collect ice.

I laid down on the couch feeling the throbbing pain in my back. I knew sometimes it could take a week for it to fix and then it could go out again at any time. I just looked at him defeated knowing that my week was going to be spent resting.

"Here, just relax and take it easy. I have some muscle relaxers you can take too." He said as he put the cold towel to my back.

"It might help. I just don't take pain meds though. I will take muscle relaxers but nothing else."

He nodded his head and walked quickly out. I just laid there pissed off that my back had given out again and that I would most likely be out of work for a week because of it. It was not missing work that pissed me off but the not doing anything that bothered me.

Rick was back quickly and fed me some pills. "Here take this and relax. You need help getting into bed?"

"Yea. I am going to need help getting to my bed." I said knowing that I was dead on my feet for at least a day.

I carefully stood up cursing in pain as he put his head under my arm helping me to my bedroom. As we got there I carefully kicked off my shoes. Rick then looked at me. "After you are better, we need to talk about your decorating. But first let me help you."

"Just need to get changed and go to bed." I said feeling the stinging pain of my back hitting my like a bunch of lightning bolts shooting to my spine.

He pulled up my shirt and then looked at me. "I am going to take your pants off."

"Okay...I just need to get in bed." I replied not even caring that a gay man was pulling down my pants. The only thing I was concerned about was that my back was killing me and I wanted to lay down.

I was in my boxers and he guided me to my bed. I cringed in pain as I got into position. I then looked at him nodding that I was set and he smiled back. "I am going to leave, but will check up on you tomorrow."

"Thank you. But you don't have too." I answered as I didn't think I needed help if I got some sleep in.

"Yeah, whatever. I will be here tomorrow to check up on you." Rick shot back smiling as I knew he really would come back.

I woke up feeling much better. I was able to stand with just some slight discomfort and even walk around with little to no pain. Rick walked in around nine and gave me a look of disappointment. "You need to be off your feet."

"Nahhh. I am doing much better today. I am just going to take it easy for a day or two."

Rick still looked at him like I was a child. "You're an ass. You are really going to hurt yourself. Have you made an appointment with your doctor?"

"Doctor...nooo. They will just give me pain meds that I won't take. It's just a nagging injury I am going to have to live with. Although those muscles relaxers did wonders. Now I know to hit you up when my back goes out again."

"What about a chiropractor?"

I gave him a stoic manly look as I knew I would never go to one nor admit that I needed help. "I don't believe in that shit. I will be fine. I just need to take it easy."

His voice hit a high pitch. "Nooo. You need to go to a chiropractor at least."

"Don't worry about me. I will be fine."

"What about a masseuse? Will you at least go to one of them?" His voice sounded concerned.

"Some hot Asian massage parlor with happy endings?" I joked as I sat down smiling at him.

"Your impossible. I know a good place that you can go to." He added as I could hear his concern in his voice.

"I am not into massages unless it's some hot Asian girl. I just don't see a need to waste money on doctors either when it goes away with simple rest."

"What about some simple lotion or some cream?"

"Fine. If you want to leave lotion here, I will put it on." I conceded knowing he meant well and was just trying to help.

"I ain't leaving lotion with you. You will not put it on and will just say you did."

"You want to put it on to make sure? I promise you I will put it on."

I could see the look in his face that he knew I was trying to pull one over on him. "I will put it on you. I don't trust you at all."

"Fine. Get your lotions and what not and you can put it on me." I gave in and knew that it was the only way he would stop nagging me.

When he walked out the door, I stripped off my shirt and laid face down on the couch. His place was close and he was back within a few minutes. "I see your already prepared."

"Put your magical lotions on me so you can be happy." I said jokingly.

"This stuff stains, you might want to take off those pants."

I pulled down my dockers so I was just in my boxers. I didn't think it was that big of a deal as it felt like a medical thing and nothing else.

I felt the cold lotion hit my back and then his hands working my lower back. "Ohhhhh....damm." I moaned giving in and letting him know that it really did feel good.

"I told you it would feel better. You need to listen to people more. I swear if Robert listened to me more, I would not have dumped him."

"Is he the one you wouldn't bring around us?" I asked, knowing his last boyfriend was kind of a mystery and we never got a chance to meet him.

"Yea. But I left him for other reasons."

"Mmmmm....feels good. I may have you do this more. So tell me the reasons." I asked giving into the pleasure and feeling the lotion tingle on my skin. I looked over slightly and saw that it was icy hot and it was doing its job tenfold.

"You wouldn't want to know. It's kinda a gay thing." Rick answered with a softer tone.

My voice picked up as did my curiosity. "Tell me. I got to hear what the gay thing is now."

"Okay, but don't say that is gross or think differently of me."

"I won't. I already figure it has something to do with butt sex." I joked as I knew he did divulge information if asked but only if someone asked.

"Well, he was cute and all, but not very clean. Let's just say when you have anal sex you need to clean beforehand. He was lazy about it and he was lazy about life in general."

I never realized that you needed to prepare for anal as I never gave it thought before. Although I did hate lazy people and only hired go-getters who hustled. I then leaned forward stretching my back. "I am not one for lazy people. I busted my ass to get where I am."

Rick continued to put more lotion on and then stopped. "Let it set in and then cool off before you put your shirt on. I did want to ask you...why you live here of all places. I mean you could have a giant mansion built and live there. I know you have money and all. That car and truck of yours costs a pretty penny."

It was the same question I heard from my other family members and almost all of my ex-girlfriends. "I own this townhouse outright and enjoy not having to worry about yardwork or anything else. When I take a vacation or do anything else, I never worry about someone stealing my shit either. I guess it's the people I live near too. I mean if I do settle down, I can rent this out and buy a house."

I leaned forward and lifted up and when I did, I felt my boxers pull down showing a bit of my backside to him. It was a slight feeling of the top of my ass showing but nothing else as I finally stood up. I then gave Rick a joking look as I saw him looking at me. "You looked, didn't you?"

I knew I was joking and hoped he did too. When he smiled back, I felt at ease that I could joke with him too. He just shot back a look and then replied. "I can't help it. You do have a cute ass. I bet the girls said that too, and you know it too. I saw you strutting your chest around a few times making sure the girls look."

"So you think my ass is cute?" I joked again smiling know that he admitted it. I wasn't bothered and didn't want to admit it was kind of flattering.

"Stop." He said with his hand up smiling back at me.

"Better ass then Rob?" I joked back walking slowly to the fridge wanting something to drink.

"I don't know. He did have a cute ass and would give it up all the times when I wanted it." Rick said with a smiley tone as I knew he was getting even with me for joking with him.

"Does it feel good? I mean, compared to pussy?" I asked wondering if gay guys liked it more than pussy or if they had pussy but chose ass instead. I knew I was ignorant but I was willing to ask. I never had a gay friend before and felt comfortable asking and not being seen as arrogant to him.

"You really want to know?" Rick asked as I heard his tone sound more serious.

"Sure. I mean I thought about fucking a few girls in the ass. Becky in High School almost let me too."

"Well...let just say nature is cruel. You know if your prostate gets touched it will make you orgasm. Not just any orgasm but a great one. It also feels good to have anal sex too as it is much tighter and if done right will feel absolutely amazing. But, sex is not just physical for me. I mean, I love being around the guy and having that connection with him."

I smiled and sat down carefully thinking about what he said and knew he was right about connecting with the person. I was told that numerous times that I needed to connect with the right girl and sex would be amazing.

As I opened my soda I watched Rick get up and sit across from me at the table. "Some straight guys pleasure that prostate too. I know a few that use toys on themselves and more that have their wife's use it."

"Whoooaaaa. Too much. I am not shoving some big dildo up my ass. I am all for have a great orgasm but toys in the ass...really?" I replied just thinking about Rick coming over with a dildo to use on my ass.

"You are such an ass. Have a girl use her fingers and then come back to me saying you didn't't enjoy it. You don't even have to touch your thing either...it will just cum naturally." Rick shot back with a smug smile as if he knew he had won.

"So, wait. You're telling me that I will cum from her fingers and not from the fact she is sucking my cock or touching me? Just her fingers, nothing else?" I inquired wondering if he was right but also asking for clarification. I knew some girls did it and was not trying to sound like a self-righteous guy but a curious one as it involved a girl giving me a blowjob too.

Rick leaned back with a big grin. "It adds to it. If she is skilled and knows what she is doing she can make you cum from just her fingers and without even touching your dick."

I was not about to let some girl shove her fingers up my ass and not give me a blowjob. I also knew it would sound gay as fuck if I just asked a girl to go exploring in my ass so I could get off. I knew he was probably right and my limited knowledge was still in the thought of the guy fucking the ass was always getting the pleasure.

"So, you're telling me..."

Rick gave a small chuckle and interrupted me. "You have been living in this area too long and have been sheltered. Let me just say that if you rub the prostate just right you will hit a climax that will make you want to do it again and again. I swear...there is so much porn about it. Then again, I doubt you would, it's not really straight porn."

"So, you're going to give me toys to make this happen?" I joked wondering if he really would.

"I could but you're going to have to find just the right spot to hit and experiment. I would keep an open mind though. Don't be saying that it's gay, but just give into that it feels good."

"I think you're lying. No offense, but I think it feels good if you gay. I do think sexual preference has something to do with it." I added as there was no way that I could just ejaculate to an orgasm with something in my ass and not have a girl involved. I know that I could probably ooze. out sperm, but no way would I get a climax from it.

Rick shrugged his shoulders and then smiled. "I bet I could give you a toy for you to use and then you would admit it."

"Not a chance."

"I would wear Alabama colors for a week if I was lying to you or you didn't like it." Rick challenged with a smug smirk on his face.

"No fucking way. First, I ain't shoving anything in my ass and no way would you go through with it." I said knowing full well that he hated Alabama with every fiber of his being. In the time he spent with us he developed this hatred for Alabama.

"All week I would wear it. That's how confident I am. But if you lose...I want something in return." He replied, still holding that smug look and crossing his arms.

"Fine, I can do some work at your place. I know you wanted some remodeling... I just want to see Steven's face when you are wearing it though. But there is no way I am telling people about this bet." I commented knowing that this had to be a secret.

"Okay. I will just tell them it was a guy at work that bet me. I would never tell a soul about this. This is a private personal dare between us."

"Okay...okay. Let's do this then. Go get you toy and we can settle this right now."

I was not totally against sexual experimentation and figured I could try it and then know I hated it and never think about it again. I also trusted Rick in keeping his mouth shut as he never once gossiped to the guys. I also knew he was the most fashion sensitive person I ever met and him going against that was worth me taking a toy in my ass.

Deeplust
Deeplust
719 Followers