It was serendipity that I lost my anal virginity

Each person remembers their first time for the major events in their lives such as going to school, a date, kiss, and sexual intercourse. For the more adventurous, anal sex can be enjoyable for both the person receiving (bottom), and giving (top). On study has reported that 40% of married couples had experimented with anal sex. The report continued by saying few men has experienced the pain and pleasure of receiving anal intercourse.

At the age of forty-three, I had my first bisexual meeting. In my early days of being bisexual, I only met men to receive head. After three years of one-way oral sex, I had a curiosity about of giving fellatio to man. Once I had a man cum in my mouth, I became addicted to giving oral sex. My bisexual activities were slowly progressing. Eventually, I changed from giving oral sex to receiving anal sex. It took me eight years to lose my virgin ass, this happened serendipity when I met a stranger named Carl.

I met Carl online. I would post messages to various Yahoo groups to find strangers to meet for anonymous sex. Carl responded with an x-rated picture of him and stated why he would like to meet me. One reason I agreed to meet Carl, he lived near where I lived, fewer than two miles. In our e-mail exchanges, he expressed extreme pleasure in receiving oral satisfaction, and I boasted that I like giving head without anything in exchange. After several e-mail exchanges we agreed to meet at Dennys where we could sit, have coffee, checking each other out to determine if we wanted to meet. My sexual needs are to have a man's cum in my mouth; Carl's sexual needs were to receive a blowjob to completion.

I met Carl at the timed agreed; we shook hands and ordered coffee. We had a pleasant conservation lasting more than an hour. We talked about our work, where we lived, and sports. At the end of our conservation, we started to talk about the subject of our meeting, the giving and receiving oral pleasure. I had an immediate liking for Carl. I liked Carl, his personality being different from other men I have met. He had a soft-spoken voice, which put me at ease. He did not appear in a hurry to meet for a blow and go. This lack of action caused me to believe Carl did not want to me so I could suck his cock.

Carl worked as a masseuse and had large hands with muscular forearms. Carl had interesting stories to share about giving massages. Some of his male clients wanted extra services such as a “happy ending” at the end of the message. Carl's massage job provided a chance of providing hand job to one, two, or more men a day.

Carl told me, "With so many naked bodies and with the hand jobs, I give out I come home horny. I want to relax and need someone to suck my cock." He continued, "I have a girlfriend, but we do not spend many nights together. She knows that I am bisexual and does not mind if meet another man."

I responded, "I like to give blow jobs, and you would not have to do anything in return."

Carl finished his coffee and said, "My place is not too far from here, if you would like you can follow me to my apartment." My spirit lifted with the invitation. Carl lived alone; he rented a two-bedroom apartment. One bedroom reserved for sleeping and the second bedroom for his massage business. We entered Carl's apartment that appeared tidy. Walking past the couch, Carl suggested, "Let's go to the bedroom." Carl used this second bedroom to give in-the-house massages. In the bedroom, I noticed a portable folding massage table, a queen-sized bed, and chest of drawers. Carl asked, "Would you like a massage?"

I accepted by saying, "Sure, love to. I am sure you give great massages. A massage would feel so good that would want a massage all the time." I stripped down to my boxers, asking Carl, "Where do you want me?"
Carl nodded toward the massage table saying, "On the table and remove your boxers." I felt a little shy about being naked, but did as directed."

Carl's hands were like magic, strong and powerful hands moving over my body, touching all pressure points. After fifteen minutes, I felt very relaxed. I did not notice, but while Carl gave me a massage, he undressed. I opened my eyes and looked straight at his cock.
Carl said, "Roger lets move over to the bed where we will have more room."

A few minutes later, our naked bodies were lying on the bed. Carl stood almost six feet tall and weighed less than one hundred seventy pounds. His body looked in first class condition reasoning his job kept him in good condition. My body compared to Carl is not trim and fit. I felt a little self-concise about my body being twenty pounds heavy, but not fat. Carl had an all-over tan with a hairy chest and legs. In comparison to Carl, I am smooth and white from the neck down.

The first thing I noticed, as I lay naked in bed with Carl, his cock. Since I have been a bisexual man, the site of another man's cock fascinates me. The fascination starts when he is still dressed, and I try to predict if he small or large, cut or uncut does his cock have a bend or is it straight? I think about whether he shoots off fast or slow; how much cum he would give me. I had fantasy about a man's cum in my mouth and swallowing.

When talking to Carl he the type of man whom you would feel comfortable with whether you were sitting on the couch watching football or like now, lying in bed, two men naked.

Whispering that he had a large cock, teasing him by rubbing around his partly hard erection, I continued to play, teasing his cock. Looking into his eyes, I could tell he wanted me to continue. In a few minutes, Carl's cock stood erect. I started to lick his shaft while cupping his balls in my one hand and with my other hand, and I held his cock moving it across my cheek and lips.

I knew what I like when receiving oral sex and just tried to do the same when I played with Carl's cock. With Carl's cock, I observed he had a round mushroom shaped head colored a wonderful shade of pink. I put the head of Carl's the cock in a warm wet mouth hoping that Carl would not come right away.

Next, I like to lick Carl's frenulum (that cute little flap on the underside of his gland; it is similar to the floppy object under your tongue, only smaller). I enjoy flicking my tongue along the shaft then toward this; Spots at the tip were I hope I would find Carl's tickle spot. I move my mouth to Carl's balls, licking and sucking them. Carl moved his legs allowing access to his perineum, the area between his balls and the anus hole. Carl has showered, so I run my tongue back and forth, finding his second tickle spot.

I lightly brushed Carl's shaft with my fingertips while I kiss and lick other parts of his body. Carl provided me a jar of coconut oil, which I used to lube his cock. Coconut oil is a solid at room temperature, melts at body temperature, and is a natural healthily food. It has no taste, unlike the most commercial lubes that taste medical. Lubrication is important when giving oral sex because the skin on the shaft of the penis is thin and sensitive to chafing.

I kissed and licked Carl's cock shaft. I circled his cock head with the tip of my tongue, tickling the frenulum with my tongue. I remove my mouth from Carl's cock and move to his balls where I suck, kiss and lick his balls, his hole and his perineum, everything. When I am between Carl's legs, he closes his eyes giving a little moan of pleasure. I did not do this for long.

I took one of Carl's nuts in my mouth and sucking gently on it. Stimulated, Carl responds to the warmth of my mouth by saying, "Oh yeah, that feels good. Suck my nut."
His cock looked bigger than other men I have met so I had to hold his cock with both hands as I began licking the head of his cock lightly. Trying to look professional I commented, "You have too many cocks to get in my mouth, thick and long." I want to make him feel powerful and confident. I am relaxing him with the encouraging words, and by the sound of my voice.

I tried to stay in control building his confidence and wanting him to fuck my mouth. I finished teasing him and eager to take on his full erection in my mouth. My mouth started sliding over the head of his penis and letting his cock slip between my lips. Beginning with small unpredictable movements on his gland, I made sure my lips were covering my teeth so not felt. Gradually, I began moving my head back and forth more vigorously.

My lips slid on his erect shaft, my tongue moving around as much as possible, massaging Carl's cock. I tickled his shaft with my tongue while his cock went, deep down, in my mouth. Next, I twirled the head of Carl's cock around with my lips and tongue. Obviously, the motion of the tongue caused increasing Carl's pleasure. Carl gasps, "Wow you are good. You sure can suck a cock."

I knelt next to Carl, with a mouth full of cock. I replied with a nod of my head. I used various techniques on Carl's cock, changing them to keep Carl from cumming. My mind thinking Carl would blow his load, in my mouth, on my face, or on my naked body. I put one hand around the bottom of his shaft. I slowly brought my lips over his erect cock head taking him all deep into my mouth. My mouth felt to Carl liked a warm wet pussy. Carl watched me give him oral sex. As Carl watched me, the visual stimulation is powerful.

I wrapped my hand around the base of Carl's cock acting as an extension of my mouth. This action kept me from gagging on Carl's cock when deep in my mouth. My hand and mouth worked together to put tension on the top of Carl's cock. I gently pushed my tongue down Carl's pee hole. As I let Carl's cock out of my mouth, I let the head of his cock slide from the roof of my mouth, producing more pleasure.

I could feel Carl's climax starting; I felt his penis getting harder as Carl arched his back. Carl softly said, "I about to cum. Where do you want me to shoot?" Carl gave me advance notice that he indented to shoot.
Like all cocksuckers, I like the taste of a man's semen and I love to swallow. All I could utter, "Carl cum in my mouth."

I decided I wanted Carl's cum in my mouth, and I wanted to swallow his cum. I knew that a man's semen is healthy and safe to take in. I wanted to swallow Carl's cum because I am submissive and by swallowing, Carl would know that I have accepted his dominance over my actions. Holding my breath, with Carl's cock far down my throat, I wait for him to shoot. He did not shoot. I moved my head back to enable me to breathe. Once more, moving down I go all the way on him again. I did several times until he starts to climax. Firmly, I locked-in my hungry embrace of my throat on Carl's cock as he shoots. I flexed and contracted my throat muscles to simulate a throbbing wet pussy. I knew Carl's cock looked ready to erupt, causing me to caress his balls aggressively. I received that feeling in my throat, of the throbbing burst of energy, the dam breaks and Carl's glorious cum floods my throat to my gut. Carl's cock dribbled his cum out his pee hole and filled my mouth. Carl's cum has not immediate taste, where he came, deep in my mouth, there are no taste's buds.

I moved Carl's cock to the center of my mouth as I continued to massage his cock in my mouth and tongue. The rest of his climax shoots cum in my mouth. Swishing his warm man cream around in my mouth, it spreads all over his cock. I keep sucking him, taking all of his cum until his erection starts to go soft. I then lick his cock clean of all his cum, ending by giving his cock a big thank you kiss on the head.

For a long time, Carl and I rested on the bed. We dressed and Carl offered me something to drink, coffee, coke a beer. I selected a beer. We sat on the couch and acted like two normal straight men. He did not mention of what we had done in the bedroom. Carl had a way of separating our bisexual activities with his straight acting activities. When Carl and I would meet, we acted as if we were two ordinary straight males. When Carl started to rub his cock or gave me an order like, "Get your hot mouth over here," did I turned into this submissive cock sucker.

I finished the beer, shook hands with Carl, and I returned home. I sent Carl a thank you for meeting and told him I had a great time.
A few days later, the cell phone rang. Carl said, "My girlfriend would like to watch two men go at it. She will not share but wants to watch. Are you interested?"
At first, I did not know what to say. Gathering my thought, I questioned Carl, "Go at it?"

Carl replies, "You know what we did a few days ago. She is hot to want to watch me and another man."
"Sure, sounds exciting to me. I love spectators." I boosted.
Carl and I discussed the time to meet and found our schedule worked to meet the next night. I parked in front of Carl's apartment in the label visitor's parking space. I am fresh out of the shower dressed in my work clothes, slacks and dress shirt.

Carl meets me at the door with a beer and welcomes me into his apartment. As I entered, a tall blond woman approached. I shake her hand and say I am Roger at the same time she says she is Mary. We smile as we sit on the couch. We start conversing about our jobs, how we ended in this town and other polite topics. We chatted about how we enjoyed living near the beach, how we met Carl. Mary stated, "Carl and I have been dating for a year."
I reply "Oh that is great." I am at a lost for words.

Mary continues no sign of embarrassment in her voice, "Carl told me about you sucking his cock, and it got me so excited I had to see for myself. So I asked Carl if you would do that again."

Flattered by her words and with a pride in my voice, I said, "I love to."
Carl chimes in, "Let's go to my bedroom where we will have more room."
We walk to Carl's bedroom, Carl leading and Mary leading me by the hand. Carl's bedroom had a king-sized bed and plenty of room; I noticed the sheets turned down and a chair next to the bed. Mary announced, "I want to watch so I will be sitting here," as she armed waved over to the chair. She said, "I want to have a good view and you two put a good show on for me."

Carl removes his clothes. I start to take off mine, and Mary sits in the chair and watches. Carl and I were lying on his bed naked. Carl's girlfriend remained fully clothed, ready to watch two men go at it. I lay down next to Carl, and because this is his show let him lead the way. When we lay on the bed Carl starts to kiss my neck, my ear then my mouth. In our first meeting, Carl and I did not make out, and this caught me off guard. I had made out with one man in my past, now for the second time I am making out with a man. Carl holds my head in his hands his lips firmly pressed to mine. His tongue darts out and I naturally open my mouth to accept. Carl is passionately frenching my mouth.

Carl's moves one hand from my from my neck but keeps constant pressure on my neck continuing to kiss my mouth. Carl's other hand moved to my breast and is fondling my nipple. He plays with my nipples. I have never had anyone play with my nipples be for, and I could feel them getting hard by his touch. Carl continues to rub, pinch, squeeze, my nipple resulting in a stimulation sensation from my nipple to the tip of my cock. Carl actions gave me great pleasure.

I am not sure but thought Carl had seducing me? I could not anticipate Carl's next move. I decided to follow Carl's lead, he is playing with my tits, and I will play his. Both of my hands were available to explore Carl's body. My hands went to his hairy chest, locating his nipples. My fingertips applied the same pressure and motion to Carl's tits, as Carl's action on my tits. I wondered, if this as much a turn-on for Carl as for me? My nipples were hard; my cock erect and I could feel a connection between my tits and my cock.
Laying on my stomach; Carl being on top of me, partly kneeling and bending over so he could kiss the back of my neck, ears and cheek. Mary sat in a chair, watching. Mary sat beside the bed, quit; I had forgotten that she there.

Carl moves to sit on my chest, moving forward he place his cock on my lips. I know what Carl wants and open my mouth. Carl rocks toward the front, my lips curled over my teeth and his cock slides over my lips. Carl rocks to the front causing his cock to enter my warm, wet mouth. I am still fondling his tits with my hands. Mary watches me licking, sucking, kissing, Carl's cock and as Carl is fucking my mouth.

Next, Carl moves to the sixty-nine position. I cannot see, but I can feel his mouth sucking my cock. Carl raises his hips moves toward my face and lowers his cock into my mouth. Carl now can slide his cock deeper into my mouth, enjoying that half his cock is in my mouth. I use my tongue to tickle the head of Carl's cock; each time he pauses, gives me a second to tickle him in all the right places.

After a few minutes, Carl removes his cock from my mouth and moves his hips so his ass is inches away from my mouth. I lift my head and contacting his hole. Carl had showered and clean. I do not mind rimming a clean man. Mary stands, leans over getting a better view. I feel her present in the room, watching Carl and I.

Carl moves again, as if his actions directed and the positions scripted. He rolls me over on my stomach. Carl kneels at my head, and I turn me head to face him. I can take his cock in my mouth, and he can use his hips to fuck my mouth. Carl reaches with his to my butt, finds my crack and fingers my hole. My ass felt tight and no or little penetration. Mary moves to the bedside table, pulls out a tube of lubricate. I sucked Carl's cock, and realized what he was going to do next.

Mary puts some lubricate on Carl's hand then Carl's hand slipped between my crack, putting lubricate on and in my hole. Carl's finger now could enter and probe deeper into my rectum. I felt no pain, but felt being uncomfortable because of a man's finger in my ass. Except a doctor, this being the first time I had a man's finger in my ass. Carl placed two fingers inside me reaching my prostate. Carl fingers inside my rectum placed a pressure at the correct location resulting in, pre-cum leaking from my pee hole. Mary is standing in a position where she can see all everything happening, me sucking Carl's cock and Carl finger fucking my ass. My pre-cum dripped on the bed sheets.

I began to enjoy the prostate massage, but I realized what to expect next. Am I ready for this? Carl applies more lubricant. Am I ready to have a man enter my backside? I read that anal sex is painful and that if not done right could do some actual damage. I did not want to say no to Mary's fantasy, watching two men.

Carl changes positions and moves behind me. I am still on my stomach with Carl spreading my legs as he knees between them. He pulls on my hips to position me for what is coming next. Carl's hands are on either side of my body supporting his weight. I can feel Carl's legs next to mine. I wonder whether Carl planned to fuck me that first time we met. Maybe he came too soon and now to meet me again he had used the excuse that his girlfriend wanted to watch. I am naked face down, butt up and exposed legs apart and my ass hole for all to see. I wondered about Carl, could a man to surrendering to his will turn him. At this point, I could look back and see Mary lying on the bed, reaching out for Carl's cock. I realized that she is guiding his cock to line up with my hole; now realized is going to fuck my hole. Anal sex is supposed to hurt, knowing this my body tensed.

Carl's cock head pushes against my hole and does not enter. He tries again; I can feel his hardness against my hole, but I am tight, a virgin and not sure what I needed to do. Carl on top in the dominate position, in command. Carl controls what is happening and what is going to happen.

I heard Mary's voice saying to me, "Relax," I did. She guided his cock again, and Carl pushes forward. I could feel him now, or feel something warm and hard had pushed past my anal sphincter. I remembered some pain but felt pleasure too. Mary continued to guide Carl's cock and reminded me to relax. Carl kept a constant pressure pushing his cock in my lubricated hole. It started to hurt now, I said so, and Carl stopped, and pulled out a little and stopped. The pain subsided, replaced with feeling of pleasure. Pleasure, as when Carl had his two fingers in my ass messaging my prostate.

Carl's cock standing hard and erect looked larger than other men did. I questioned if I able to take all of him into my hole. I cried out about the pain. OK it is better now; he inched his way until I felt him stopped. He started to use his pelvic to thrust his cock far down in me then withdrawing so he can push far in again.

I could feel both sphincter muscles grab Carl's cock tightly and holding him firmly as his cock slides in my sphincter muscles holding the penis. Carl felt me as tight and warm. I can feel my body reacting to this abuse with a twitching, clamping and throbbing. Carl's hard cock penetrated my rectum causes me to be involuntary react by setting up rhythmic contractions, causing a "massaging" sensation along the shaft of the penis.

I could feel the pressure build up; I felt myself going to cum and could do nothing to stop it. My body no longer in control, resigned my climax happen. I let out a cry or shout, "I am cumming." With that, my body contracted, I jerked uncontrollably. My sphincter muscles got tight, cum oozed out of my pee hole; I have a wave of extreme joy, well-being when bang. Carl plungers his cock deep into my bowel, he grabs my hips says, "Oh shit I cumming. I am going to cum in your ass."

With that, I felt a flood of warmness in me; the jerking of his cock deep inside me, his moans of joy as men comes. He lays on me; I can feel his full weight. He is heavy but not too heavy; his mouth is near my ear; I can feel his breath, hear his exhaustion, Carl whispers, "Wow Roger; you have a tight ass, and everything a hot fuck." Mary sat back in the chair; I looked at her; I had a smile on my face, and so did she.

My ass contrasts like having a bowel movement; Carl's cock squeezed out, and I hope there is no mess. I do not want smell or see any crap. I feel wetness between my legs and figured Carl's cum leaking from of my hole.

Carl rolls of me, grab a towel, cleans his cock of cum, and lucking no brown stuff. He gives me the towel, and he heads to the shower. I lay there trying to clean the creamy mess between my legs. I felt somewhat used, but in a nice way. Carl had a nice place to put cock and cum. I remembered how I felt to have a man deposit his sperm in me. I did not anticipate that it would be a wonderful feeling. I liked it; I like being on the bottom and having the man do the fucking.

Carl finished showering; I took a quick shower, got dress and returned to the living room where, Mary and Carl were sitting on the couch. I entered the living room; btoth got a smile on their face. Mary asked, "How was that? Did you enjoy Carl's cock in you?"

I responded, "It was an experience. It hurt at first. However, with Mary's help and I relax. I would have never realized that all of Carl's cock would fit." I can still feel Carl's cock deep inside me cumming. Mary and I were comparing notes abut Carl's cock. Mary asked me how I liked Carl fucking my hole. Carl looked a little embarrassing about the conservation.

After that first time of having anal sex, I became addicted a submissive bottom. I met Carl several more times, but he did not fuck me again. What Carl did when we met is another story.