Bisexual's First Time

Story Info
My first time with man to man sex.
6.1k words
4.43
205k
60
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
CuckoldGuy
CuckoldGuy
1,072 Followers

This true story is dedicated to my wife, "To all those blow jobs she never gave me, I experienced them outside of our marriage."

*

There have been events in my life that stand out and no matter how long ago, I can remember them with exact clarity. Every detail, moment by moment and word for word as in this account. This event occurred many years ago, before the dreaded AIDS virus claimed so many creative men.

It was a Wednesday evening and it was my wife's turn to host her bridge club at our house. Not wanting to be home with a house full of women, I decided to go to a movie.

After buying my ticket, I was walking across the lobby toward the entrance way to the darken theater, when I saw a gentleman standing near the entrance. He was well dressed, in a suit with white shirt and tie. I thought that perhaps he was the theater manager. He was about two inches taller than my five foot, ten inches and he seemed to be about ten to fifteen years older than my forty-two years. He was a handsome man, with a full head of salt and pepper hair, with a matching mustache, well trimmed.

As I walked toward him, he began smiling as if he knew me. I smiled back as I turned and entered the darken theater. I walked down about five rows and then turned into a row and sat about four seats in. As it was a Wednesday night, there was hardly anyone in the theater.

Just as my eyes became accustomed to the dark, the gentleman appeared at my row and walked up to me, asking if I would mind if he sat in the seat next to me. I answered him saying, "No, of course not" and he sat down placing his hand on the arm rest. When he did, I noticed his manicured finger nails.

Then I felt his knee press against mine. I did not pull away and just felt the warmth between our knees. Then his hand moved down onto my knee and slowly slid up the inside of my thigh which caused me to get an erection. His hand soon found it.

I snaked my hand under his arm and felt him in the same manner. Feeling through the material of his pants, I could feel his large erection and I whispered to him, "Do you have a place where we can go?"

"I have an apartment about five miles away, if you want to follow me."

I whispered back, "Let's go," and we got up to leave. I followed him out of our row and when he got to the aisle, he stepped back and waited for me to pass in front of him, much like a gentleman does for a woman.

When we got to the exit door of the theater, he opened it and held it open for me. He walked me to my car and told me to wait there, while he got his car, so I could follow him.

In the parking lot of his garden apartments, he helped me out of my car and walked me with his hand on the small of my back to the door of his building. He unlocked the door and again held it open for me so I could pass in front of him as he said, "Just up these stairs."

I walked up the flight of stairs to a landing where he unlocked the door to his apartment and held it open for me. The apartment was well appointed and very neat. I complemented him and he said, "Thank you. I have a woman who comes in five mornings a week and straightens up for me. It's a lot cheaper than getting married. Let me take your jacket and I'll fix you a drink. I'm going to have a scotch and soda. What can I get you?"

"I'll have a soda."

"I have Coke, ginger ale or club soda."

"A Coke would be fine," I answered. We stood in the kitchen talking about our jobs as I watched him prepare our drinks. Then we moved into the living room and he indicated to the couch for me to sit. It was soft, luxurious and very comfortable as I sunk into it.

He excused himself for a minute, went into his bedroom and came out holding a pair of slippers. He sat down next to me and untied his shoe laces, taking off his shoes, he put on his slippers saying, "I just need to get comfortable."

He left his tie on and I thought that was odd. The first thing I would take off to get comfortable, would be my tie.

His name was Brian and he was an accountant. I asked him if maybe he could do my taxes. He laughed saying that he was not that kind of accountant. That he worked in M and As, mergers and acquisitions. Two years ago he moved into this area from Denver. I told him of my job and life as a married man with children. We were having a good conversation and getting along well. I was saying something to him, when he took my drink from my hand and placed it on the coffee table in front of us. He then leaned in and kissed me on my lips.

How gross, I thought to myself as he was kissing me. A man kissing a man. I was shocked. He was kissing me and I could feel his mustache pressing into my upper lip. I thought to myself, "How revolting. I've never in my life kissed a man on the lips. How disgusting is this."

He broke the kiss and studied my face for my reaction. We said nothing. He was just studying my face for an expression. I wasn't angry but I felt violated. Looking deep into his eyes, I could see a kind person. He lives alone and must be lonely. He seems to be so considerate, so sensitive and so gentle. How could I do or say anything that would hurt him?

He leaned in to kiss me again and something changed within me. I let him. This time I kissed him back. I pressed my lips to his. I responded like a woman. I felt like a woman. I placed my hands around the back of his neck and pulled him to me, just like a woman. I felt his tongue touch my lips and I opened my mouth. His tongue darted into my mouth and I started sucking it. His hands were all over me, undressing me and I was helping him.

When he had me completely nude, we continued kissing. He kissed my neck, my shoulder and then he started sucking my nipple, just like I would do to a woman. My erection was straining and I couldn't wait to get it in his mouth. I applied pressure to the back of his head, to push him down to my cock but he resisted.

I was completely nude and he was fully dressed, I kissed him again only this time, I reached for his belt buckle. I wanted to get him nude so that we both would be equal. I felt his hand on mine and he stopped me saying, "We'll get to that in a moment," then he whispered, "And you'll love it."

Now that we were intimate, his style of conversing changed. He spoke in a slow, soft, sensual almost hypnotic tone and after he would say something, he would then whisper a comment. It was almost like he was talking to my conscious mind and whispering to my subconscious.

He took a sip of his drink and then turned sideways to me, so he was now facing me. After studying my face for a few moments, he began, "When I see a young man that I want, I have to work pretty hard at getting him up here to my apartment but you, you were very easy, almost too easy. In fact, when you were following me here, I started to get concerned, that maybe you were going to hustle me."

I tried to set him at ease by saying, "I assure you, I'm not a hustler."

He replied, "I can see that now but I'm curious about you. You said that you're married, have kids, you're a family man. What I find puzzling, is how did you get here? I mean, what life's path led you here to me? Have you always played around with men?" Then he whispered, "The truth."

I could feel my erection deflating as I answered, "No. I never played around with men. It's something that just started recently. It's a long story."

"I've got time."

"I was married very young and soon after getting married, my wife started cheating on me. She was getting her sexual excitement and I was left alone. She never gave me a blow job and as a result of my loneliness, I turned to other women. They would give me a blow job and I would end up, falling in love with them.

"The last girlfriend I had, all she ever wanted to do was blow me. She was convinced that male semen was good for her hair and skin. She did have the most luxurious sheen to her auburn hair and her complexion was soft, milky white and flawless. As a result, I became addicted to her sucking me off. We were in love but she had a husband and kids and I had my family. We were getting too involved with each other, so we both felt it was best to end the relationship, before we ruined both our marriages. That was about three years ago."

Then I fell silent thinking of her. She was one in a million and I should never have let her go. Brian broke my train of thoughts as he spoke, "I think I get it. You never really had a relationship with your wife."

"No, I didn't. She married me just to get out of her parents house. She could have been the center of my life. She could have been the most exciting person in my life but she refused to be honest with me. I could live with the adultery, it was the secrets and lies that destroyed my love for her."

He asked, "So why are you staying with her?"

"I'm not going to leave my kids alone with her and besides, she's a good housekeeper."

"I see." Brian probed some more, "So when did you start having man to man sex?"

"About three years ago. It was about two weeks after I broke up with the girl I was telling you about. One night I was real randy, so I went to an adult book store, just to look at a video and maybe jerk off. I met a young man in the video area of the store and he asked if we could share a booth. He ended up giving me a blow job.

"It was the first time I ever had a guy go down on me. It felt weird, having a man do that and to hear him gagging as I came in his mouth. He swallowed it all. Then I just wanted to get out of there. I pulled up my pants and as I was leaving, he thanked me.

"I felt bad for the guy, I mean something had to be wrong with him, to be doing that but about six weeks later, I was back looking for the guy. As it turned out, every five or six weeks, I would go there and get a blow job. This went on for about a year."

I took a sip of my drink, I needed some time to reconsider what I was doing. I don't know why I was sitting here naked, telling this stranger all my deep secrets. My clothes were scattered around the floor. I started to feel embarrassed but at the same time it was also erotic. Maybe I should get dressed and go home. I fell silent, not wanting to go on and yet not knowing what to do. Then he adjusted his tie saying, "Please go on with your story." Then whispered, "I'm very interested."

That simple movement of him touching his tie, made me aware of my nakedness and caused me more embarrassment, which led to passive and submissive feelings. I placed my drink back on the table and folded my hands over my now flaccid penis, in an attempt to cover myself and preserve some of my dignity.

I continued, "I don't know if I should tell you this but anyway. About two years ago, I got a massage from a male therapist. He was a big burly, bald headed guy. I don't know if he was bald or he shaved his head. He had his office in a back room of his very expensive house.

"I was laying nude on his table, on my stomach with a small towel covering my back side. He massaged my arms, back and then moved down to my feet. The warm oil felt so good as he rubbed it into my flesh. His hands moved up my leg and then to my thigh. As he worked up the inside of my thigh, I started to become aroused and I spread my legs apart for him. I got an erection and I raised my hips up off the table, to give him access to my genitals.

"It was then that he removed the towel and poured some oil on my buttocks. His hands felt very erotic as he massaged my buttocks with his fingers sliding into my crack. He kept sliding his fingers across my anus and I became highly aroused, pushing my hips up even higher off the table for him.

"By then, I was breathing very heavy as his finger massaged my anus. It was so sensitive to his touch. I wanted so much for him to finger fuck me. He knew how much he was arousing me. My face was resting on the edge of the table and he came around to me. He was naked from the waist down and he had an erection which he put in front of my face, just inches from my mouth.

"He started massaging the back of my head, trying to coax me into sucking it. He was persistent and I was so aroused, that after a while, I reluctantly opened my mouth. He then stepped up to me and pushed his erection all the way into my throat and for the first time in my life, I had a cock in my mouth.

"Still holding him in my mouth, I got off the table and knelt in front of him. Sucking his cock felt like the most natural and comforting thing to do. After sucking him for a while, he began breathing heavy. He took my head in his hands and using his legs, he wedged me against the table. I felt his body stiffen, then he grunted and I felt his hot cum flooding into my mouth. I tried to pull away but I could not move. I squirmed trying to get his cock out of my mouth but he held me fast. I choked and gagged, gasping for breath as his cock pumped and pumped my mouth full of his hot cum.

"When he finished, he released me and I ran into the bathroom, gagging with my mouth full of his semen. I tried to spit it all out into the sink. It was awful, so hot, gooey, slimy and stringy. I rinsed out my mouth over and over. Then I wet my face and dried my face and hands.

"Returning to his table, I still maintained my erection and he told me to get back on the table and he would take care of it. I lay on my back and he continued the massage as if nothing happened. After he massaged my front, he took my erection in his oiled hand and stroked me to climax.

"After I was dressed, I paid him and left, vowing that I would never do that again. I felt so ashamed and guilty for weeks after but six weeks later, despite my self loathing, I returned to him for another massage.

"As he was giving me the massage, he asked me if that was the first time I ever sucked a cock and I told him yes. He said he was sorry about being so forceful and he would go easy on me this time. This time when I was sucking him and he was getting ready to cum, he told me to try and swallow the head of his cock. He told me to just keep swallowing and I won't gag. He kept telling me to swallow as he grunted and pumped all of his semen down my swallowing throat. This time, I didn't gag and I didn't taste his cum.

"Every five or six weeks for a year and a half, I visited him, until about three months ago, when his wife was transferred to a higher paying job so they moved out of state. I still feel guilty about what I do but I'm starting to accept myself for who I am. Like that young man at the book store, I'm a cock sucker. I can't help it."

He adjusted his sitting position so we were now side by side and he put his arm over my shoulders, caressing me as he said, "You're too hard on yourself."

I sighed, "Yeah, maybe I am. That's pretty much my sexual history. I've told you everything. Maybe you could tell me a little about yourself?"

"I'm afraid my sex life isn't as varied as yours, it's rather simple. My very first experience was fucking a guy in his ass and I've been doing men that way ever since."

"Have you ever had a girl?"

He answered, "Yeah. Tried a bunch of girls, they just never did anything for me. I just love fucking a young, firm male ass. They become so humble after I've taken them," then he whispered, "And they love it."

He took my chin into his fingers and turned my face to his like he was going to kiss me, saying, "I'm glad you told me about your masseur. How you enjoyed his finger in your ass and how turned on it made you. You're lucky. Some men never get to experience that."

I meekly replied, "No, I guess they don't."

He was intently studying my face as he began, "These past couple of years, you've been discovering man to man sex and now tonight, I would like to give you the ultimate pleasure. I'd like to teach you the joys of anal sex." Then in a whisper, "You'll enjoy being fucked."

I was getting concerned, "No. No. Please, I've never done that."

He frowned at me as he said, "This night has been going so well. You're not going to disappoint me now are you?"

As he was talking, he was rubbing his hand back and forth across my lower belly. I felt like I was going to be taken advantage of. I was starting to feel a little panic. Maybe I should get dressed and leave but then I don't know why but I said, "No. I don't want to disappoint you. I just don't think I can do that."

"Have you ever tried it?"

"No. Never."

He continued in his calm, soft hypnotic tone, "I can't believe, that no one has never introduced you to anal? You don't know what you're missing. Once a man has had that, then he wants nothing else. Let me be the one who gives it to you. I'll be very gentle and if at any time you want to stop, just say the word no and I'll stop. Is that fair?"

"Yes but I think it will hurt."

"No. It's not going to hurt." Then in a whisper, "It's very pleasurable."

His voice was very soothing and I began to relax a little. Knowing that I was not going to get the blow job I had been anticipating, my penis was now flaccid.

I was still nervous and he had a way of making me feel very passive and submissive. He stood up and there was a very noticeable tent in his trousers. He took my hand in his and said, "Come in the bedroom."

His bedroom was only a few steps away and as we walked, he put his arm around my upper back, then slid his hand down and cupped the globe of my bare buttock. Feeling his hand on my buttocks was very arousing and I felt that I might enjoy this.

When his bed came into view, I got a sick nervous feeling in my stomach, thinking of what was to come. He pulled the spread back off the bed and then pulled the covers back, revealing the clean, crispy, white sheets. Then he said, "Wait a minute."

He walked into the bathroom and emerged carrying a large, folded bath towel. When he came out of the bathroom, we made eye contact. I watched his eyes scanned down my naked body, stopping at my flaccid penis, then back up to my eyes and when he did, I don't know if he smiled or smirked at me. A smirk that seemed to say, "Well my young man, You came here expecting a blow job but instead, you're going to be fucked."

He knew my predicament; I was completely nude and he was fully dressed. Tonight he had been out hunting and now he had his prey, me. I felt so vulnerable, so embarrassed of my nudity and my submissiveness.

He took the pillow from the head of the bed and placed it in the center of the mattress. Then he draped the towel over the pillow and sheet. He must have done this a hundred times.

Then he turned to me, taking me in his arms and caressing me, I could feel his erection pressing against me. We kissed, with me once again sucking his tongue. As we kissed, I felt his hands slide down my back where he started feeling my naked buttocks, squeezing them and running his fingers into my crack.

I had my arms around him as I caressed him, feeling his strong back muscles. Then his hands felt their way up my back, where he placed them on the tops of my shoulders. Kissing me on my forehead, he applied a slight downward pressure and I sunk to my knees.

His hands hung down at his sides as he watched me unbuckled his belt, then his zipper. I lowered his pants and as I did, he kicked off his slippers. Then I lowered his white, silk boxers, taking care not to hurt his erect penis.

What a beautiful penis. A long, thick, white shaft that seemed to be about six inches long with another two inches added for the large, fat, pink head. It looked like an over sized lolly pop, just too large for what he wanted to do to me with it. I took it into my mouth and sucked it like a starving animal, gagging several times. I wanted him to ejaculate. I wanted him to go flaccid so he wouldn't be able to jam this long, large cock up into my bowels.

While I was sucking his cock, he reached down and took my head into his hands. Holding me still, he pulled his cock out of my mouth, denying me a chance to make him cum. He pulled me up to him and indicating to the bed, in a gentle but commanding voice, whispered, "On your tummy."

CuckoldGuy
CuckoldGuy
1,072 Followers
12