1st Time Exploring My Bi Side With Two Men

gay man and bisexual man

The Wednesday evening winter rush-hour drive was smooth with the exception of my butterflies and nervous knots in my stomach. I continued to ask myself if I was really ready to go through with the meeting and interview process. As I pulled into the subdivision and parked in the dedicated parking spot for the address, I reminded myself that this was an excellent way to break the ice.

Let me backtrack. Actually, my butterflies started the week prior in an e-mail exchange and several phone calls with the moderator of a local bisexual swinger’s group on a well-known adult themed website in 2003. I had stumbled across the group’s posting while looking for like-minded singles or couples. There it was, a well-written description of the bi swinger’s group, complete with several photos depicting the group’s erotic composition. I decided then to send them a note to introduce myself. Why not give it a try.

At that time, my bio noted that I was forty years old, five foot nine, one hundred and eighty pounds and in good shape, seven inches cut, safe, clean, shaved smooth, divorced, bi-curious, and looking to enjoy both him and her or a group to explore my bi fantasies. Yes, I was still a bi virgin.

A few days passed before I received a response from the group’s main contact, Robert. Our e-mail exchanges were quite pleasant and started off explaining the rules of the group, the telephone interview, and the personal interview process. We also exchanged some photos, both of the group that was not on the site and of myself, for the approval process. I was quite pleased with the photos I saw and was extremely relieved that they responded expressing their interest in me. After several e-mail exchanges, Robert asked if I was ready for the telephonic interview and if so, we would need to set up a time to chat. Now I was crossing my first hurdle, giving out my phone number. That was part of the test. Was I actually interested? If not, I wouldn’t let them call me. I was interested.

The phone interview with Robert had lasted about thirty minutes and was quite professional and not absurd. More than anything else, it allowed us to chat covering most of the same items already laid out in the e-mails as well as the fact that they limited the amount of single men in the group and wanted to ensure a proper fit. At the end of the call, we agreed to meet the following Wednesday evening for a tour of the property where the group met and to make sure we were all truly comfortable with each other. I would find out whether or not I would make the cut.

Fast forward to my arrival. I sat in my car for a few moments to make sure I had gathered my composure and to remind myself that it was just an interview of sorts. However, I had still showered and shaved. And to answer the question up front, yes, I am clean-shaven there too. I dressed in black slacks and a white Polo shirt, even wearing sheer bright blue mesh briefs that would accentuate my throbbing hard cock if I were asked to disrobe as part of the interview and approval process. My black cashmere overcoat provided the warmth needed that cold winter evening.

I finally opened the car door and began the short walk up the sidewalk to the all-brick end unit townhouse where the front porch lights blazed in the chilled air. I climbed the porch steps to the landing and took a deep breath before pressing the doorbell and waited for someone to respond. The door opened just a few moments later and I had my first opportunity to meet Robert face-to-face. He was dressed casually in dark slacks, loafers, and a button down blue business shirt opened at the collar and red power tie hanging loosely. He welcomed me in with a smile, shaking hands and introduced himself as I entered the foyer.

He was at least five years my junior, black hair, warm smile, strong handshake, and immediately put me at ease as he asked if he could take my coat and if I would like a drink. I removed my coat and handed it over as I looked around the beautiful townhome. I asked him what he was drinking and when he told me scotch, I smiled and said I would love to have the same.

Robert was the consummate host and gentlemen. We chit chatted about traffic and directions to the home and what a busy day he had at work as I followed him to the kitchen to pour my drink. I took notice of the photos and pictures on the walls of the living room and hallway. I commented on the marvelous way the house was decorated. He mentioned that he and his wife had purchased the property as a second home for when they were in town. They spent most of their time in Florida. He noted that his wife would be back in town for the group party the following weekend.

We chatted as we sipped our scotch and he asked if I would like a tour of the house. Nodding my approval, he beckoned me to follow him through the main level first, showing a den, the formal dining room, and back to the foyer and formal living room area before heading up stairs. Walking up the stairs to the second floor, he let me walk in front of him. At the top of the stairs, he commented on my nice ass in the slacks and smiled. This was a test to see if I was actually interested. We looked each other in the eyes and I could see the smile developing and his eyebrows moved and a quizzical way letting me know that the interview was going well. I smiled back.

He pointed toward the master bedroom at the end of the open hallway. I walked ahead to the doorway and paused. It was then that he moved behind me, slightly to my right side, and slid a hand softly on my ass and leaned in to smell my cologne. My butterflies were gone, whether it was the scotch or I was just that comfortable with him at that point, I wasn’t sure. I melted when he whispered in my ear, “Love your cologne and your ass,” as he firmly clasped my ass.

I sighed and let my right hand rub against his thigh as he leaned into me, slightly brushing his hardening cock held hostage in his slacks and underwear, against my palm. “Very nice master bedroom. Love the four poster king sized bed,” I said as I turned to him.

He responded with a smile and pressed himself against my hand and noted, “There are three bedrooms up here and the full finished basement with another bedroom, entertainment center, bar, fireplace, and access to the hot tub in the privacy fenced back yard downstairs.”

My cock was now throbbing and needed to be rearranged in my own pants and briefs. Yes, there was definitely sexual tension in the air. I moved forward and surveyed the bedroom as he leaned in the doorway now taking another sip of his scotch. I tried to casually adjust my equipment easing the discomfort I was having and he nodded with approval and noted, “I know. I’m having the same problem.”

I peeked into the master bath and saw the huge tile and glass shower, complete with bench and room for six and a huge Jacuzzi tub. There was a huge walk in closet only half filled with business attire, both for him and her. Walking back to the doorway, I smiled and continued to peek into the other rooms before heading down stairs. Robert asked me to follow him down stairs to see the finished basement.

Now it was my turn to watch him walk down the two sets of stairs. I also enjoyed the view. At the bottom of the steps, I saw that the gas fireplace was lit, displaying a warm glow to the room, and the television was still on. He must have come down stairs when he came home. He walked to the glass patio doors, pulled open the drapes and turned on the outside lights to show off the large covered outdoor hot tub.

“Now that you’ve had the tour, is there anything else you would like to see or know about our group? ” After a slight pause, he continued. “You look like you need to refresh that drink, would you like another?”

I smiled and held out my glass as if to relinquish it for him to refill. He pulled the curtains closed, turned off the lights to the back yard and walked over to take my glass. “I’ll be right back,” He noted. “Make yourself comfortable down here. I’ll only be a few minutes.”

I watched him walk back up the stairs. I sat down on the sofa and waited for his return. I was surprised to notice that the television was actually showing a porn movie and had the volume on mute. The scene on before me had a woman and two men engaged in a three-way oral endeavor where one well hung stud was between the woman’s spread legs on the sofa and the second was getting a blow job from the woman at the other end of the sofa. The woman released the hard cock she was sucking and moved into position on all fours as the other guy rolled on his back and slid under her spread legs to work on her gaping pussy. I searched for the remote and turned up the volume to hear the moaning and slurping sounds of oral sex and pleasure.

It was quite an erotic and extremely hot scene but the scene got even hotter when the second stud crawled between the open legs of the stud eating out the woman and slowly grasped his massive cock and began to lick and tease the massive tool before trying to devour it. I was lost in the scene. When he slid a finger in his ass, I squirmed and my own cock wanted to burst from my pants.

I hadn’t noticed how much time had passed but I looked up to see Robert coming back down the stairs with two glasses of scotch. He had also changed, and more importantly, he had taken a shower and now padded down the stairs in a thick black terrycloth robe. “I see you found the remote.”

“I did,” I responded and reached for my glass that he presented me.

He smelled fresh of body wash and a gold chain caught my attention falling down his chest and disappearing in his robe. His hair was slicked back, allowing it to dry naturally and after he handed me the drink, sat down next to me with his legs curled up to his side.

He smiled over his glass and commented, “Sorry, but I really did want to take a shower. It’s been a long day.”

“I understand. I did the same before coming here as well.”

I looked back at the movie to see the woman move to straddle her lover’s mouth while the stud who had been working the massive cock moved to lather some lube onto the massive cock he had been sucking with such determination. When he climbed up onto the sofa and straddled the massive cock, I must have sighed with anticipation of what was about to occur, because Robert leaned over and whispered in my ear, “Oh, this part is so hot, he takes it all.”

It was then that the stud grasped the massive cock, lined himself atop the head and slowly slid down onto the throbbing tool. The close up of the pulsing cock disappearing into that ass was so hot. Robert slowly nibbled on my ear and then began to kiss my neck. I could feel myself melt under his touch. I was relaxed and also highly aroused with my own cock throbbing in my pants and a hot hunk wanting to test my bisexual curiosity. Robert’s hands roam across my chest, unbuttoning my shirt and then pulling it over my head. I slid off my loafers and then turned slightly toward Robert to allow him access to my belt and pants. I felt like I was being stripped and about to be made love to by my own stud.

As the actor moaned in pleasure as he was slowly fucking the throbbing cock, Robert moved me slightly to have access to unbuckle my belt. He then unbuttoned my pants and slowly slid the zipper down as he gave me my first male-to-male kiss. The first kiss was soft and lips closed. The second was lips slightly parted and to see if I would respond, and did I. I allowed his tongue to enter my mouth in a hot deep French kiss that could match any I’ve had with any woman I’ve been with up to that moment. Taking a lyric from Katy Perry and modifying it would be an accurate testament of that kiss. I kissed a boy and I liked it.

I now knew I was his as he began to slide my slacks off and I lifted to allow them to slide down my legs without breaking the hot kiss. I remember doing the same with women and now it was happening to me. He broke the kiss to slide down and remove my socks leaving me there in my mesh briefs and throbbing cock straining the material. He slid back onto the sofa and moved me back again positioning himself to kiss me deeply again. I heard the moaning from sexual pleasure on the movie and could feel my own tension continue to build. I could feel his hardness press on me as he leaned against me, taking my hands and moving my arms above my head giving him access to me.

He broke the kiss and began to nibble down my neck and then to my chest taking the time to slowly suck my sensitive nipples causing my cock to throb even more, which I didn’t think was possible. He moved down slowly across my stomach and then came to the mesh briefs encasing my own throbbing cock. He slowly and lightly ran his tongue down my shaft, still covered by the mesh, teasing my cock with each lick. He did this for several minutes, teasing me and causing me to moan louder from the erotic pleasure he was giving me just before moving down to the insides of my legs and slowly nibbling all the way down to my ankles. In no time, he started back up the inside of the other leg. I thought I would explode.

By the time he reached my cock on his upward trek, I was leaking precum. Apparently this was evident to him because he took the time to lick and suck the tip of my cock through the material in an effort to get a taste before he actually devoured my cock. He finally pulled the mesh briefs slowly down, letting my cock pop up from its entrapment of the briefs and leaving me now totally exposed for his and my pleasure. He stood up to survey me lying before him before crawling back between my legs to begin to give me an exquisite blowjob. His oral skills were magnificent. His tongue was magic across my cock, under the head, down the shaft, slowly licking and tonguing my slick shaved balls, and then making circles around my asshole before penetrating with such skill.

When he moved back up to engulf my throbbing cock again, I ran my hands through his hair and down his neck. He was so focused on pleasuring me that he knew when I was about to cum. Sensing my pending climax, he squeezed the base of my shaft letting the sensation ebb before bringing me back again to the brink of climax. Again, I had no sense of time. My lover was skilled, that was for sure.

When Robert finally wanted me to cum, he told me to cum in his mouth and let him drink my load. I moaned and shook my head yes, my hips now pumping my cock into his greedy mouth and throat. I felt his hand beneath my ass and a finger slide into my hot hole. He found my P-Spot almost immediately and began massaging it with first one and then two fingers. He pushed me over the edge and I moaned loudly and yelled out several times, “Oh my!”

I thought I wouldn’t stop cumming as wave after wave of hot semen erupted from depth of my balls up through my cock and shooting into the greedy and wanting mouth of my new lover. I shook, more like convulsed, as I came. I was in total ecstasy.

I felt his fingers slide out of my ass, leaving me with a feeling of emptiness. He then released my cock from his mouth and looked at me with a smile and he asked, “How do you feel?”

“Oh my,” I responded. “Or better yet, oh wow! That was amazing!”

“Why thank you,” he replied. Then he looked at me and asked, “Would you like to try your first cock? I know one that would love your attention.”

I smiled back and noted, ‘I would love to pleasure you. I hope I do well enough for your pleasure. I want to learn to do everything you did to me and more.”

“Well, yes there is some experience to it but, remember. You know what you like when someone sucks on your cock. Not every woman knows how to make you truly squirm. But you know what you like. Just think of it that way. I’ll coach you along the way.”

I sat up as he stood before me. As I rose to my feet my own cock now hung down, not quite soft and not quite hard and my heart raced. I leaned in to untie his robe letting the robe’s belt drop to the floor. I slid my arms around him pulling him close and kissed him as he kissed me. He shared the saltiness of my own cum as our tongues swirled in the erotic French kiss dance. I let my hands drop to his ass and felt a silk thong at his waist with the thin strip of material running down the crack of his ass. I let my right hand wander to the front and felt his cock throbbing in the sheer material, the head peaking over the top of the thong.

I let my left hand slowly slide the robe off his right shoulder and then slowly fall from his left. Now, it was my turn to finally experience a throbbing and massive cock in my mouth and to try to tease him in the same manner that he teased me causing my tremendous orgasm. He was slightly thicker and longer than my seven inches. I inspected his throbbing cock head peaking out from the thong. He already had precum spilling forth waiting for me to taste. I dropped to my knees and let my tongue swirl at the tip of his cock, my first taste of his cum. Oh what a wonderful taste. I could hear moaning on the television again as I maneuvered Robert back onto the couch with my back to the entertainment center.

I let him get comfortable and left his thong on him at first. I wanted to tease him, the thong providing an erotic feeling as my tongue glided up the length of the shaft from the base to the exposed tip. His moans included, “Oh fuck yes, do it, just like that.” Again, time seemed to disappear as I slowly began to study and make oral love to my lover’s hard monster cock.

When I pulled the thong down exposing his throbbing well-manicured manhood, I went to work on each and every square inch of it. When I finally took the head into my mouth, I swirled my tongue around the head and then down the underside as I let his cock fill my mouth. I knew not only was I comfortable with him making love to me, I was extremely comfortable making love to him. I slowly began to fuck his cock with my mouth and tongue, making sure to pay extra attention to that sensitive spot under the head before engulfing him, each time trying to see if I could get him into my throat. He reminded me that it may take time but I was doing quite well. Of course, I kept hoping my gag reflexes would give in for me.

As he did to me, I let one finger enter his ass as I worked his cock. Then I added two. He moaned with pleasure but coached me again by adding; “I love three fingers in me, give me three and fuck my ass while you suck me.” What a coach.

I could feel his balls tighten and I backed off, letting his cock slip from my mouth with a plop. His cock pulsed in front of me as I squeezed the base of his cock to try to stop him from cumming. I did get more precum and I was able to thwart his orgasm several times, even keeping my fingers in his ass as he pushed against them burying them deep in his hot box.

When he finally told me he was ready to cum, I tried to apply each trick he did to me in order to make his climax an awesome orgasm. I slid a fourth finger into his ass, opening him up and applying pressure to his prostate. I didn’t think his cock could get any harder but it jumped and throbbed even more. Then he told me he was going to cum. He grabbed the back of my head and fucked my mouth like he was pile driving a hot pussy. I was determined to make sure I sucked the juices out of his cock and not letting his eruption go to waste on his stomach or elsewhere.

When he came, it was in waves as I had done, but in such a massive quantity. I struggled to keep up with the load. He erupted into the back of my throat and I greedily continued to suck the seed from his pulsing cock. “Hey,” he said. “Remember to save some for me.”

I did. I let his cock plop from my mouth and I moved up to kiss him with unbridled passion. The passion that comes from someone consumed with the heat of sex and erotic acts of two passionate lovers. I truly enjoyed kissing him. He gave back passion and I knew we were not finished for the night.

“Well, let me say that you were pretty remarkable for your first time,” he commented. He lay back against the arm of the sofa and reached for his glass of scotch.

I adjusted myself and found my glass at the end table. “I could use some ice,” I noted.

Robert got up and grabbed me by the hand and we walked up the stairs like two lovers having an intermission between sexual romps. He grabbed some ice for each of our glasses and poured a slight touch more of scotch over the ice before sipping again. “Let’s go upstairs, that is, if you would like to continue our date this evening.”

I nodded and replied, “I would love to.”

I followed him back upstairs. He had already prepared the bedroom when he went up to take a shower and change. The bed was pulled down; there were several bottles of lube, plugs, and dildos on the nightstands; and a sex blanket throw was on the bed. “I see you had ideas. What would you like to do?” My eyebrows arched as I asked the question.

His cock had already began to harden and mine was also aroused after bringing him to climax downstairs. “I want to fuck your ass, that is, if you would like to try it. I want to show you more tonight.”

I moved to the bed, took another sip of my scotch, and placed it on the nightstand coaster next to a large bottle of Astroglide lubricant. I climbed up onto the king sized bed on all fours, my ass up in the air and said, “I want to have you fuck me. What position do you want me in?”

“Well, that is a good first position. Turn around and grab the headboard and leave your ass up in the air for me.”

I did as I was asked and maneuvered around exposing my ass for his pleasure, which I quickly found was actually our pleasure. He pulled an orange and white tube from the nightstand drawer and placed liberal amounts of the white cream on his fingertips. I asked him what the cream was and he told me Anal Eaze. It was a desensitizing cream and it would help me through my first anal experience. As he massaged the cream around my puckered ass hole and then into my hot box, I could tell that there was a pleasant pressure as he probed my ass instead of a sharp piercing pain I had anticipated. Even down stairs, his fingers were magic in my ass.

After a few moments of easing the cream in and around my virgin ass, he began to apply liberal amounts of the Astroglide to my ass, forcing some into me. He then coated his now fully erect cock and placed his hands on my hips. I knew he was safe but I had always thought my first anal fuck would have been with a condom. At this point, he positioned himself behind me and let the head of his cock press at my lubed asshole.

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5 thoughts on “1st Time Exploring My Bi Side With Two Men

  1. TomofNorway says:

    Yes, VERY hot story – bringing back memories of a couple similar personal experiences more than a few years ago – along with sensations so aptly described in this story! I have to admit I’m not a huge fan of “completely shaved”, “neatly manicured”, totally smooth or ‘sating bikini’ — but the scenarios are top rate! I prefer the furry, masculine types and descriptions, but these type of stories are completely arousing!

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