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Bisexual's First Time

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We said nothing as I lay there, my hips on the pillow with my anus raised up, yielding to him. My heart was pounding in my chest. My mouth went dry and I had a lump in my throat. I watched him pick up his pants, fold them and place them on the near-by chair. He took off his socks, his tie and shirt, all the while with every move, his erection bounced in front of him, glistening with my saliva.

He was now nude, so beautiful. The last thing he took off was his wrist watch and he placed it on the night stand, next to my face. I saw the dial; eight forty five. An hour ago, we were two strangers passing in the night and now I'm nude, in his bed, waiting for him to sodomize me.

After he placed the watch, he went into the bathroom and returned with a jar of vaseline. He scooped out some on his finger, then he spread my buttocks apart and I felt the coolness of the jelly on my anus. He pushed some of the lube into my anus and his finger felt so pleasurable. I didn't want him to stop.

I watched him slather a generous amount of lube on his erection. Then he wiped his fingers clean on the towel and in a soft, considerate tone of voice, he whispered, "Spread your legs."

I felt the mattress moving as he climbed up between my legs. There was silence as I felt his gentle hands, slide up the outside of my thighs and then onto my buttocks, where he gently petted them.

Then in a soft voice he said, "Relax. Just relax, let it happen naturally." His hands spread apart my buttocks, exposing my rosebud and then I felt the large, hot head of his erection, begin to press apart my buttocks as he pressed it towards my opening.

Just when the tip of his cock touched my anus, my body reacted involuntarily by jerking, stiffening and tensing up. My buttocks clenched tightly together, squeezing out his penis. "I'm sorry. I'm so sorry. I didn't mean to do that. I couldn't help it," I pleaded.

He was understanding as he continued in his calm voice, "That's Okay. It's Okay. Relax. Just relax. I understand. Just relax."

His gentle hands were petting my buttocks as I listened to his soothing voice, "Calm yourself. You're trembling so much. I'm not going to hurt you in any way."

Then he whispered in my ear, "You're safe with me."

I calmed down and began to relax and then he asked me, "Are you ready to try it again?"

"Yes. I think so."

"Good. Now just relax. Don't think about it. Just let it happen." As he was talking, he slowly began to push it in and the same thing happened as before. My body clinched up, expelling his erection from between my buttocks.

I was too nervous and tense. My heart was pounding and I was trembling. I thought he would become angry and frustrated but no, he continued softly talking to me and gently massaging my buttocks. After a while it seemed to work and I calmed down and started to relax.

Speaking in his slow, soft, hypnotic voice, "We don't have to do this just yet. Let's just cuddle and let you get use to me. Let me lay on top of you like this so you can feel my cock next to your love hole. Just let the head rest next to it, like this. That's it." Then with his mouth against my ear, he whispered, "Relax."

I couldn't help being nervous. I was trying to relax but the head of his cock felt so big.

"Just relax. I'm not going to force you." Then he whispered, "We'll do it when you're ready."

I felt his belly fill in the contours of my back as he lowered his full body weight on me and the head of his cock was now once again pressed against my anus, only this time I was a little more calm. All the while I'm listening to his gentle hypnotic voice saying, "That's it. Relax, rest and relax. Let me get a little more comfortable." He moved his legs so they straddled mine.

He combed his fingers through my hair, complimenting on it and then he clutched a handful in his hand saying, "I love the feel of your hair." Then a whisper, "It's so silky."

He had me pinned. I could not move and I did not protest. Whether I wanted it or not, I was going to be fucked. He brought his other hand up and held it open in front of my face, softly saying, "Don't be nervous, just relax." Then a whisper, "Kiss my hand."

I started to kiss the palm of his hand, when he suddenly, clamped it over my mouth and at the same time, he made a sharp, violent stab into my anus with his cock. We both let out a groan; his in pleasure, mine in pain. The head of his cock was now in me and he held us very still. I could feel my sphincter muscle tighten around his shaft, locking his cock-head inside of me. I don't think he could have pulled out if he wanted to.

With his mouth against my ear, he whispered, "Are you Okay?"

"It hurts."

"It hurts because you're not relaxing. Relax and it won't hurt. Just let it happen. I'm sorry I did it the way I did but there was no other way. Just relax."

"I'm trying."

"Calm yourself. You're panting like a wounded animal. Take a deep breath and hold it. Good, now exhale. Take another deep breath. Keep taking deep breaths. That's good. You're doing good. Now I'm going to push it in a little bit more?"

"Oh, please don't move it. Keep it still. Oh! Ohhh! Oh, Brian it hurts. I can't catch my breath! I can't breathe. You're too heavy." I panted.

"Oh, I'm sorry." He lifted his weight up off of me and I felt a little better.

He was concerned about me and he asked again, "How does it feel now?"

"It's so hot. It feels like a burning hot poker." I could feel the heat radiating out from the head of his cock into my whole body. I started perspiring.

He continued, "Just relax and let your body get use to it. Are you ready for a little bit more, or do you want me to pull it out?"

I sighed, "No. I think I can take more of it."

"That's my girl. I'll give it all to you, every last inch of it. Oh yes, it feels so good going in. You're so tight. Hmmm this is all of it. How are you feeling?"

"I feel so full."

"Any pain?"

"No. No pain." I panted.

"How about when I move it in and out, just a little like this?"

"It feels good. Feels so good."

He started thrusting harder and harder into me and I started thrusting back up to him, meeting his thrusts. Perspiration was pouring off of me. It felt like my anus was on fire. All the while he kept saying, "Now you're my girl."

"Yes! I'm your girl," I growled back as he pounded into me. It felt so incredible. The sensations were unlike anything I've ever experienced. Not like intercourse or getting a blow job where the sensations are centered on my penis, here the sensations were through-out my whole body.

By now, we were both on our knees, dogie style with Brian hammering into me. Our testicles were swinging and slapping against each other. I could feel his cock growing harder, hotter and larger as he neared his climax. Then he made one final thrust, clutching my hips with his hands, trying to give himself more purchase as he pushed himself even deeper. His body jerked and he began ejaculating deep in my bowels. Pushing into me with each ejaculation until he was spent.

He let his full body weight press me into the mattress as he laid on top of me, fully exhausted with his penis deflating inside of me. The violence was over and I felt so at peace. We laid like that for a long while and then he slipped it out of me and said, "Lie still. Don't move."

He got up and went into the bathroom, coming back with a box of tissues and a waste basket. Taking a handful of tissues, he wiped into the crack of my buttocks saying, "This sometimes gets messy."

My anus felt like it was all torn open and bloodied. I could feel a warm wetness and I asked, "Is it blood?"

"No, no. The vaseline gets like oil and I just don't want you to get it all over everything."

After he cleaned me, he went into the bathroom and at the sink, washed his genitals with soap and water.

Laying there I became aware of a wetness on my stomach. I lifted myself up and discovered that I was laying in a pool of my own semen. I didn't realize that I had ejaculated so much during our rutting.

It was considerate of him to wash his penis with soap and water as he soon had another erection. This time he ejaculated down my throat and I in his, as we shared in a sixty-nine.

Later that night, when I left his apartment and was walking across the parking lot to my car, my posterior felt so open. It was causing me to walk like a woman and all night long, from the first time I spoke to him in the movie theater, to saying good night to him, the tone of my voice has been soft like a women's. I had to get out of this female persona and get back into my male mode, before I get home.

By the time I got home, my anus felt all open and wet. I went directly to the bathroom, thinking that I must be bleeding from my rectum. How am I going to explain this? Wiping my anus with tissue, I found only his semen, mixed with some lubricant.

Six weeks later I was back at Brian's apartment. Prior to meeting with him, I had purged my bowels so that I was clean for him. This night, I was to learn that he preferred to have me lie on my back so he could drape my legs over his shoulders. This way we could look into each others eyes as he entered me.

I had an erection when he started to pound into me and I was going to stroke it but Brian stopped me saying, "No, don't touch it, just watch it." We watched it until I began ejaculating, just as Brian climaxed inside of me.

Brian and I got together like this, every five or six weeks for the next seven or eight months and then the news media began reporting about a mysterious disease that was killing homosexuals. I knew Brian was having multiple sex partners so I immediately ended my relationship with him.

My doctor was very understanding when I confessed to him what I had been doing. He ran all of the blood tests and found nothing out of the ordinary so he declared me in good health. I then asked him if he could give me a prescription to curb my sexual cravings. He prescribed a heart medication that would have no effect on my healthy heart but it had the side effects of diminished sexual desire and function.

The cycle of my homosexual cravings occur every six weeks with a duration of two or three days so I only had to go on the heart medication for a week, every five weeks. This went on for two years, until I learned how the dreaded virus was being transmitted. I adjusted my life accordingly.

I limit my sexual relations to only like minded, married men and I follow the safe sex guide lines. Very quickly I had to revise my limitations; I was with a married guy, in his early twenties and I was his first, man to man experience. I was trying to put a condom on him but he became so excited, that he tried to rape me. I had to fend him off and in our struggle, he ejaculated all over my body. After that episode, I only partner with married men, thirty years of age or older.

12
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24 Comments
AnonymousAnonymousabout 1 year ago

That older man was an abuser.

AnonymousAnonymousalmost 2 years ago

I found this story to be very believable, but not erotic.

AnonymousAnonymousover 2 years ago

Very hot! I love how gentle the older man was with him.

AnonymousAnonymousalmost 3 years ago

I thought it was hot. The kissing part made me hard as hell!

AnonymousAnonymousalmost 3 years ago

Awesome story very erotic

Bearjer69Bearjer69almost 5 years ago
Hot!!!

I would love to have had an experience like this.

AnonymousAnonymousover 5 years ago
Good Story

This sounds like a very true story and one that many men have lived in some fashion. I to have had some experience but nothing like this, thanks for your story.

AnonymousAnonymousabout 9 years ago
Fantastic!!!

I remember my first. It did feel funny kissing, but if you can put his dick in your mouth, kissing sound silly! He opened me up with a very large silver bullet vibrator. I knew if I could take that, then his cock would be nothing. I like to sit on a cock or dildo first. It lets me control the pace and depth. After that I told Mike to take me like a bitch! And he did, making me cum just from the ass fucking!!! More!!!

AnonymousAnonymousabout 9 years ago
To the comment that AIDS isn't a virus

True--AIDS isn't a virus, but it is caused by a virus--HIV.

AnonymousAnonymousabout 9 years ago
Face Down, Ass Up

Nothing like this position! My journey from straight married man to fully bisexual sissy husband had several key points, but not long after our 2nd anniversary she let me know that my smallish thin cock was not satisfying her. She didn't want another man, just wanted to change up our lovemaking by reversing our roles. Once I'd gotten real good tonguing her pussy and bringing her to orgasm, she introduced a dildo play, and after a couple of months of sucking my wife's strap-on dildo and her fingering my ass she draped me over a pillow one night, face down and ass up and gave me the fucking I've never been able to give her. The signs were all there - my submissiveness, the complete joy I had of her fucking me the way a dominant man fucks his woman, and my total acceptance of this role.

It was several years later that she told me a new co-worker was gay and having trouble meeting people in our conservative southern city. She had him to dinner several times and by the 4th or 5th time, him observing my cooking and general submission to her, he asked if we were married or just roommates. The question caught us both off guard, we all laughed and my wife said, "We're married, it's just that I'm the man of the house!" He understood, and from that point began flirting with me. In time, he had me draped over pillows in the living room, our bedroom and his at his apartment, fucking me like the submissive bi-sissy I am.

AnonymousAnonymousalmost 10 years ago
Just one thing...

AIDS isn't a virus.

triedbisextriedbisexalmost 11 years ago
What a wonderful encounter

I've never thought about kissing another man. In my mind that WAS gross, but sucking his cock to completion was ok. After reading your story, I realized that kissing a man would be a turn on and a first step to making love. I do want to try it now.

I don't think I want to be penetrated, but hell if I can kiss a man, then maybe ill try being fucked

devilspy2001devilspy2001almost 11 years ago
Good story, need more like it

As a bi top who enjoys introducing cuckold's to their pussy, this was a good story. Many wives love to see their husband suck cock and swallow but few break their husbands pussy in. Many cuckold begin to see hung tranny tops to get stretched and bred. Like the story said, all of my cuckold love getting fucked and bred. We need more story's like this. About the less discussed side of being a cuckold with a little cock. There is more to the life of a cuckold than just chastity and being cut off from their woman's pussy.

AnonymousAnonymousabout 11 years ago
Oh, the First!

It was at a family reunion that I finally heard the story of my wife's first time.....she lost her virginity in her 16th summer at her grandparents' farm. A young uncle took it. Two weeks after the reunion he took my anal virginity as well, when he invited me to his apartment to pick up some old albums. He seduced me from the minute I walked in, insisting that I was not man enough for my wife, even though we'd been married 6 years by that time. His forceful kisses, incredible back and butt rubs, and finally twisting my nipples until I was on my knees in front of him led me down a path that I'm still trying to figure out. One thing for sure, I'm a much better homo bottom than hetero top!

DeborahAnneDeborahAnneover 11 years ago
Love to be taken that way

I was masterbating in my bedroom and rolling up and sucking my own cock to get the cum. My step-father came in to explain sex to me and we ended up sucking and fucking each other many times. I love to have a bare cock in my mouth and to swallow that precious cum. I use dildo's now in my butt as I can not find a man in my area of Indiana. Care to chat use

penisholderpenisholderover 11 years ago
great story

I am bisexual and want to have this happen to me . I have sucked cock and had men cum and I lovedthe taste and power it gave me . Thanks for the story.

AnonymousAnonymousover 11 years ago
Wow

This is amazing, whoever wrote this is an amazing author. They managed to put the seductive hypnotic voice of the man into my head and I felt like I was really there. I love it.

AnonymousAnonymousover 11 years ago
4 stars

I got turned on while reading your story. I have never had sex with a man. When i fantasies about it i take all kind of roles but if he fucks me i am on my back my legs over his shoulders. If i am fucking him he's on his back in the same position. O sorry i almost forgot, 69 is the best but in a combo with other positions.

I have decided to have sex with a man if i get a chance.

AnonymousAnonymousover 11 years ago
Awesome!

This story is hot and very well done. I would really love to have a first time experience like this. My strongest fantasy is to be fucked in the ass bareback while on my back like a woman. I get hard just thinking about it.

AnonymousAnonymousalmost 12 years ago
First

Married,27,had looked at some porn,went into a adult movie booth,flicked through,came to a gay movie,watched for awhile as a guy fucked in and out of a guys arse and my cock grew hard.I fucked my wifes arse,not as often as i wanted,she said it was not natural,but i remember once,she kept pushing back,gripping my cock as she orgasmed,my cock jetting cumm deep into her tight arse.Now watching the movie,i wondered what it would feel like,a cock deep inside me and my cock shot cumm.I played handball,after a hard game,which i lost because i pulled a muscle in my leg i went to shower and my older opponent who had defeated me asked if i wanted a drink.I looked at him,said o.k.the courts were closing and as i limped out,James said why not come over to my place,i will help you with that injury.I thought why not,rang my wife,said i would be a little late.At his place,James asked where the injury was,i told him the groin area.He told me to take off my shorts,lay down,i did,and he came back with warm oil,lifted my leg onto his shoulder and began rubbing the oil into my groin area,occasionally brushing my balls.My cock started to grow,how embarrasing as he rubbed the oil down my groin and a oiled finger brushed my bottom,then my balls and along my cock.Oh my,my cock hardened,James lifted my other leg,both on his shoulders now,more oil on his hand and onto my cock,stroking,then back to my hole,a finger moving around then gently pushing inside,moving around,in further,oh my cock was rock hard.He pulled his finger back,my legs still on his shoulders,pulling me forward,then more oil around my hole and then for the first time the head of a mans cock at my entrance.I wanted it,i whispered yes,as he leaned forward,it wouldnt go in,i heard him say relax,try to open up,i did and the head slid into me.I felt stretched,a shot of pain,i tried to clench my hole but couldnt,his hand stroking my balls,i relaxed and i felt his cock slide into me as he leaned over me,waiting until i relaxed again and moved back,just leaving the head of his cock in me.Then forward,easier,my cock had gone soft but as he fucked me my cock grew harder.oh i felt full,he told me he was going to cumm,he stroked my cock once,my cumm shot towards and over my head as i felt warmth inside me as James pumped me full of cumm.I regularly play handball with James,he always fucks me after the game,once in the shower when we thought everyone had gone,but the male cleaner saw us,he told us not to stop and lowered his pants and stroked himself as he watched,shooting his cumm onto my back.

AnonymousAnonymousalmost 12 years ago
Hot.....!

That was the "hottest" sexual story I have ever read. Thanks for sharing it with me and thanks for giving me the desire to have this kind of experience in the future.

AnonymousAnonymousalmost 12 years ago
Finally a story I can relate to!

Loved your story! I'm a married man who likes to have a hard cock once in a while, so i can relate to this story. keep up the great writing..

AnonymousAnonymousalmost 12 years ago
if you try it it is the only thing you want

OMG memory , souvenir , i did it with my best buddy from 18 to 22 , one of my girlfreind told me if a guy try sex with another man ;that's it, he will be hock for life dreaming about cocks all the time , so for a kind of a dare to myself , i did it ! with my best buddy ,just once : maybe just a second time ; just one last third time , and so on ,and so on , cocksucker ,69, kissing , ass licking , and the so addictive ass fucking , giving and receiving , she was absolutly right i tried cock and WOW i became an addict. we were our only partner so it was perfectly safe , since then only girls, now i'm a married man , wife is a dream but i want it all , her sexy ass , and a safe cock on the side , it been 15 years the last time i did it , i LUST for cock , i need to find soon another safe married guy so we can live our dirty messy sexy dreams and do those so natural breeding things men do to each other ; you can write me ; willf96 at hotmail.com , i miss cock SO MUCH , is there another,,sane, cool, bad cheating husband to play with anywhere near ? i'm so hard !!!

William smythWilliam smythalmost 12 years ago
A remarkable story!

The very best story I have ever read about a first time experience.

Another 5 Star effort from this talented writer.

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