An Old Friend Helps Out

An Old Friend Helps Out

His first time playing catcher

The drive was long and gave me plenty of time to think about what I was doing. I was nervous about meeting up with Rick and Bob to spend the night with them. Mostly I thought about what was going to happen later that night and how long it had been building up to this point. I was sure I wanted this to happen, but I was still feeling a little conflicted. After all, I had been straight all my life, but here I was heading to meet two friends that were gay and planning to have sex with both of them.

Well, being perfectly honest, that straight all my life thing isn't really accurate. I have always been attracted to women, but once in high school when my teenage hormones where raging I let a friend suck my dick while on a sleep over. Then later while in the military stationed overseas I was so horny I let another airman suck me off several times. It felt good when they sucked me and I got turned on enough to ejaculate, but it was just a sexual release. And of course, I had no desire to reciprocate.

As I drove west I thought about the night I took the first steps down the path to tonight's rendezvous. It was a couple of years ago when during a night of sex with my wife I let her anally penetrate me with her dildo. Although she had played with my ass in the past she had never put anything in me other than a finger, but that night she wanted to use her dildo on me. She loved anal sex and wanted me to experience what it felt like for her. Our foreplay had been intense and I was dancing on the edge of orgasm with her finger buried in my ass when she said, "I think Zeke wants some of this ass." Zeke is her pet name for her dildo.

I stopped eating her pussy and said, "What? What are you talking about?" I loved it when she used her fingers on me. The sensations that flashed through me when she stroked the sensitive tissue surrounding my anus could bring me to a high state of arousal, but up until that moment I had never even thought about being on the receiving end of her dildo. In my state at the moment I wasn't entirely opposed to the idea. I just didn't know if I had heard her correctly. I didn't want to seem too eager either.

"I want to use Zeke on you. I want you to let me put him in your ass and fuck you like you do me. I think you might like him once you find out how it feels. You know you like my fingers. This is just the next logical step. Come on baby. Let Zeke fuck you."

Thinking about how much I liked to fuck her in the ass and how good her fingers were feeling in mine right then I couldn't think of a good reason not to let her have her way with me. We liked anal sex and playing with each other so much that it had become almost routine for us to use an enema before sex. I wasn't eager, but I was curious. "Okay. You can use Zeke on me, but if I tell you to stop you have to promise me you will. No questions."

"Oh baby. You are going to love Zeke. I just know it. I will be so gentle you will not feel a bit of pain. I bet that before he finishes with you, you will be begging him to fuck your ass hard. But I do promise to stop, no questions, if you ask me to. The first thing you need to do is roll over so I can get Zeke."

I rolled off of her and lay on my back. She got up and went to her dresser to retrieve her dildo. When she turned around she was holding her dildo against her crotch with one hand. In the other was a bottle of anal lube. As she walked back to the bed she cooed, "Oh baby, You're going to love Zeke."

She got on the bed between my spread legs and took my cock in her mouth. Her blow jobs were amazing and this one was no different. As she sucked me she put the head of the dildo against my anus. I was trembling with trepidation not really knowing what to expect and hoping it didn't hurt too much. Although her fingers had felt pretty good I wasn't a hundred percent sold on this idea. Zeke was about seven inches long and maybe one and a half inches thick. A little bigger than me, but not by much. I thought that if Ruth could take me in her ass I should be able to handle her Zeke.

She let my cock slip out of her mouth and said, "Raise your legs for me. You know the drill."

I did as she wanted and raised my legs. Using my hands I gripped myself behind the knees and spread my legs wide for her. It felt weird laying in this position. I felt completely vulnerable exposing my whole crotch to Ruth like that. That feeling faded as she went back to sucking my dick. I could feel pressure against my anus as she tried to work Zeke into my ass.

Ruth coached me, "Push back like you are trying to poop and it will help." I did as she asked. She pushed and the head slipped into my rectum. I felt my sphincter expand as the head slid through it. She had lied about the pain. I felt a sharp hot pain for a brief second. It was gone almost before I could react.

Ruth stopped moving for a few seconds to let me get accustomed to Zeke's size before she started pushing in again. I could feel every inch of that dildo as it slid home. Not ever having a man's dick in my ass I had nothing to compare the feeling with, but what I felt from the dildo filling my rectum was arousing. The pleasurable sensations that washed over me when Zeke filled my rectum continued as she reversed direction and withdrew. Without removing the dildo she reversed direction and filled my ass again. This time she went deeper and I moaned as Zeke plowed new ground. After several strokes she was fucking me with full length strokes. I was taking all 7 inches of Zeke and loving how it felt.

Ruth was stroking my rock hard cock as she used Zeke to fuck my ass. We were staring into each others eyes and the smile on her face told me how much she was enjoying my reaction. I dropped my gaze and watched her hands stroking me. My cock was leaking copious amounts of pre-cum making the head slick and shiny.

I was amazed when I realized I was on the verge of cumming. Surrendering to the sensations I came. The first stream shot straight up my body and left a trail of ejaculate from my neck to my belly button. Several more spurts followed. By the time I quit cumming my upper body was covered in cum. It was a very strong orgasm, to say the least, that left me weak and breathing hard. I could not remember the last time I came so hard.

All I could do was look at my wife and sigh before I said, "Oh god, baby. That felt awesome. I had no idea it would feel like that."

Ruth laughed and said, "I told you you would like it." That night Ruth using her dildo to fuck my ass changed me in ways I was yet to realize.

Since that night she has used Zeke to fuck me countless times. I love the feeling of it sliding through my sphincter and sinking deep into my bowels. Soon after that first time Ruth bought a harness for Zeke so she could use him on me hands free. The first time she fucked me with the harness it felt totally different. It felt great when she held Zeke in her hand, but this time she was behind me holding onto my hips as she rammed her cock into me. Fucking me with everything she had.

The feelings that were elicited this time as she fucked me took it to another level. No longer was it just sex play. This was raw and I knew I was being fucked. It thrilled me when I realized I was the submissive one that night. I was not the one in control; Ruth was. I could feel my dick swaying beneath me as she pounded my ass. That night was the first time I had an orgasm without my cock being touched. I shot my load into the sheets and howled from the excruciating pleasure Ruth gave me.

Since that first time Ruth kneeled behind me and used her strap-on to fuck me I wondered what it would be like to have a real cock in my ass. To have a man holding my hips tightly as he pummeled my ass. I was embarrassed by those thoughts. I couldn't bring myself to tell Ruth that I thought about letting a man fuck me. We incorporated my anal into our routine and every time she slid Zeke into me I fantasized it was a man instead of my wife.

Slowly the fantasy expanded. I started watching porn videos and reading stories about the exploits of bi sexual men when Ruth wasn't around. They would get me very aroused and we always had really good sex when Ruth got home. Of course the videos and stories where more than anal sex. There was a lot of cock sucking too. After watching guys suck one another in several videos I started wondering what it might be like to do that too. What would it feel like to suck a guy's cock to get him hard so he could fuck me? I was a little shocked when I realized that thought got me aroused too.

One Saturday when my wife was out shopping my curiosity got the best of me and I decided I was going to try it out with Zeke. Instead of watching videos on the computer I found Zeke in his resting place under a stack of my wife's panties. I took him into the bathroom with me. I locked the door; fearing that Ruth would come home and catch me doing the unthinkable. Sitting on the commode I looked at the dildo in my hand and it unnerved me thinking about what I was about to do. I equated sucking dick with being gay and I kinda thought that I might be secretly gay if it had come to this.

After all, I loved being fucked and here I was about to put a dildo in my mouth imagining it was a real cock. I quelled those thoughts and brought Zeke to my lips. I tongued the head and it did nothing for me. I opened my mouth and put a couple of inches of Zeke in. I closed my mouth and started sucking. It was very life like, but I'm not sure it felt life like in my mouth. Although it was made of soft silicone it did not feel the same as my dick when I stroked myself. It felt and tasted like plastic, but it turned me on to imagine I was sucking some guy's cock.

A guilty thrill coursed through me as I continued to suck the dildo. My dick had gotten hard so I started stroking it. Before I knew what was happening I was sucking Zeke hard and taking most of him in my mouth as I masturbated. I choked myself a couple of times when in my enthusiasm I pushed Zeke in too far, but I kept it up until I ejaculated. It was a strong orgasm and I shot several streams of cum onto the floor. Post orgasm guilt and shame for what I had done washed over me, but I couldn't forget how good my orgasm had felt. I cleaned up my mess and put Zeke back in his place well before Ruth came home.

After that first time sucking Zeke I quit watching videos. Instead I would use my wife's absence to suck Zeke and masturbate myself to orgasm. In spite of the plastic taste of Zeke I still enjoyed the sensation of him in my mouth. The feelings of guilt and shame faded quickly. I no longer thought of what I was doing as deviant, but I still hid it from Ruth. I was unsure how she would feel about it. On those occasions, sex with Ruth that night was exceptionally good.

After awhile I started thinking about an old girlfriend from years ago and how she could deep throat my dick. I loved how that felt. No one else had ever done that to me. I got to wondering if I could do it with Zeke too. The first time I tried to take it all it gagged me so bad when it entered my throat that I almost threw up.

Instead of giving up I persisted in trying every opportunity I got. After multiple tries I learned to control my gag reflex somewhat so I was able to take all of Zeke with only an occasional small gag. Once I was comfortable deep throating Zeke I liked how it felt as it slid into my throat. My orgasms during those sessions were very intense and satisfying.

I was proud of the skill I had taught myself and I flirted with the idea of showing it off for Ruth. I thought she would get a thrill out of watching me deep throat Zeke while she was wearing him. How wrong I was. One Saturday Ruth had gone shopping and I had my usual session with Zeke in the bathroom. Horny as hell when Ruth came home I talked her into having a little afternoon delight. It didn't take much persuasion; Ruth was ready for sex at the slightest hint I was interested.

We stripped naked and got on our bed. After the cursory blow job and me sliding my cock into Ruth and fucking her until she had her first orgasm she decided to invite Zeke to join us. She got out of bed and went to the bathroom. When she walked back into the bedroom Zeke was prominently displayed, suspended from Ruth's harness.

As she waked to the bed Zeke swayed from side to side. Overcoming my intuition I decided that it was time to show off my new skill. Before Ruth could get on the bed I sat up and put my feet on the floor blocking her path. Thinking it would turn her on I said, "Oh baby, I want to suck your cock." I put my hand around Zeke's girth and slid off the bed to my knees. All that happened before she could react, but when I put my mouth around Zeke and sucked him she pulled back sharply.

Looking at me I could see the shock on her face as she exclaimed, "Jack! What the fuck do you think you are doing?"

I was stunned. In my mind I thought that she would get super aroused watching me deep throat her cock and it would lead to an awesome ass fucking for me. Instead she was furious. My intuition had been correct.

With anger in her voice she berated me. "Jack, you know that shit's not right. That's so queer. What made you do that? That's just too gay for me. You're not turning gay on me are you?"

I tried to blow the whole thing off as a joke. After all, I had barely got the damned thing in my mouth when she ripped it away from me. "Holy shit, Ruth. I was only joking around. I thought you'd get a kick out of it. Sorry if I upset you."

"Well, it did upset me. Me fucking your ass is totally different from you sucking a cock. Don't ever do that again."

"Oh, don't worry about that. I don't know what got into me," I lied, I just thought it would be funny. Sorry."

Ruth seemed to except my apology, but there was a stern warning couched in her reply. "I forgive you for the mistake, Jack. Just remember. I am the only cocksucker in this household."

That was over a year ago and I have shied away from even touching her dildo when she is around. I continued my fantasy sessions in privacy thereafter. That fantasy has led me to this drive I am on tonight with the expectation of having it become reality.

Knowing the way Ruth felt about me sucking cock was very frustrating because I was thinking about it to the point of obsession. I didn't want to cheat on her, but my desire to find out what sex with a man was like was dominating my thoughts. Finally I convinced myself that it was only sex. That I could do it one time so I could satisfy my overwhelming curiosity.

I started browsing gay hook up sites on the internet, but I couldn't bring myself to message any of the prospects I found there. I really didn't like the idea of hooking up with a stranger. I had been struggling for months when one day out of the blue a potential solution came to me. I thought of an old friend that just might want to help me out.

Rick was an old family friend of Ruth's. I had met him when he attended our wedding so I have known him for ten years. Ruth and I married late in life. She had already been married and had three grown children. Rick was a childhood friend of theirs and he was treated as family. Rick was openly gay but that never seemed to be a problem with anyone. He always showed up once or twice a year for family get functions. He was a nice guy and I liked him once I got to know him.

The thought of asking him to let me suck his cock made my pulse race, but I didn't have the courage to contact him. He lived a couple of hours from us so that contributed to my dilemma. Rick became part of my fantasy. The more I fantasized about him the stronger my desire became to ask Rick for help.

I had been racking my brain trying to figure a way to make it happen when another get together was planned. It would be the perfect opportunity to ask him; if I had the nerve to go through with it. There was one slight problem. Rick had a partner. He and Bob had been together for several years now and I wasn't sure how he felt about having some side action. There was only one way to find out for sure. I made sure that they were invited to the cook out.

When the day of the cook out arrived I was on pins and needles with anticipation. This was the first time I had seen Rick since I started fantasizing about him and I was very nervous. Rick and Bob greeted me warmly; as always, giving me hugs instead of hand shakes. As the party ramped up I found myself talking with them more than anyone else. I was looking for the opportunity to pop the question.

We had some great conversation catching up on our lives for the past six months. I noticed that Rick made several comments that could be taken as innuendo. Like, "You know I'm gay, Jack, but I got to tell you you look great. I like that you have lost some weight." He was also a little handsy; at times touching my arm while making a point in conversation or once he pushed gently on my chest, just so happened his hand was on my breast, as he laughed and rebuffed whatever I had said. It could have just been my heightened sense of anticipation, but I got the impression he was sounding me out. Being slightly aroused I decided this was the perfect time to tell Rick what I had been fantasizing about and ask if he wanted to be the guy. All I needed was a chance to speak to him in private.

I got the chance to get him alone while Bob was occupied playing a game of Cornhole. As a side note I am amazed every time I hear someone say, "Do you want to play some corn hole with me. In my youth those two words had a way different meaning. I often wonder if the guy who invented the game and named it Cornhole laughed all the way to the bank every time someone said that.

Throwing caution to the wind I asked him if he wanted to share a joint of some good herb I had been holding onto for a special occasion. I thought that would be a good enough excuse to get him far enough away from the party so I could bring up my fantasy. He said yes and we walked away from the main party so we could share it in relative privacy. We walked out into the neighbors pasture to smoke as I lit the joint. As we walked and traded hits I nonchalantly asked him if he found me attractive. He stopped walking and cocked his head a little to the side. I nervously turned to face him and found myself holding my breath waiting on his response. He finally said, "Yes, why do you ask?" I expelled the breath of air in a rush and took a hit off the joint before answering. It was all or nothing now.

"Well Rick, I was wondering because you are being very attentive and touchy feely today. We have always been good friends, but today seems a little different. You don't know how ironic it is, but you have been on my mind for quite a while now. Please don't take this the wrong way; but do you want to have sex with me?"

"What makes you ask that question?" He didn't seem upset. Just curious.

"Well, you see, for the past year or so I have been having bi curious thoughts and you are the one guy I think I would like to try it with." Then everything came out. Once I got started the whole story gushed out of my mouth. I thought it might have been too much, but I couldn't help myself. I told him all about Ruth using her dildo on me. I told him about my private sessions with Zeke. I told him about the path I had been walking that led me to that moment and that I thought I was ready to find out what sex with a man was really like.

Rick's mouth was hanging open way before I finished talking. "God damn, Jack. I'm flattered that you want me to be your first. I do find you very attractive, but I never thought you would be receptive to my advances. Maybe I have been a little more attentive to you today. Maybe I felt a new vibe from you, I don't know. The thing is, I would love to have sex with you, but I won't cheat on Bob. Now, if you might consider including Bob we could work something out. We have had another person join us before so I think Bob would be up for it. I know it would be your first time and the thought of being with two guys might be overwhelming, but I promise you that everything will be perfect. If you want me to I'll talk to Bob and let you know if we can help you out."