He shot off for a minute or so, and I felt like his cock was filling up my entire skull. After he was all done, I savored his dick as it went soft in my mouth.
We both fell asleep that way, with my face between his legs. Later I was woken up by Gene pulling me up in the bed. He started kissing me on the mouth and I responded by kissing him back. He gave me a real hard French kiss, and then he spread my legs. He then started nibbling and sucking my neck, working his way down my front, covering my tits, belly, thighs and ass-cheeks with warm, wet kisses. This got me really turned on. He then put two pillows under my ass and spread my legs wide apart. He then produced a jar of K-Y jelly and started rubbing it on his big cock and putting some on my asshole. I knew then that it was going to happen, that in a few moments that big dick would be up my ass and I would be in for the biggest new experience of my life since I was born. I was excited. I had made up my mind that this would be my life from now on.
Gene started rubbing the head of his dick around the edges of my anus. Then I felt the head enter me. The head of his dick was so big and my ass was so tight that it was a difficult thing to pull off. But there was no turning back. As Gene stared passionately into my eyes and I stared back, I thought of all the women who would have killed to be in my position.
Gene then started slowly putting more and more dick up me until I didn’t think I could take any more. In the woman’s voice I had developed, I suggested that maybe that was enough. But Gene said that I was going to be his woman completely. With one huge thrust of his large body, he drove that whole ten and a half inches all the way up my ass. I was screaming with ecstasy, and Gene answered my cries of passion by saying, over and over again, “Oh, yeah. Oh, yeah. Oh, yeah.”
Gene lay still until his cock settled in my ass, and then he started slowly fucking me.
Then the magic started. This ass-fucking I was taking started to feel better than anything I had ever done before. So good, in fact, that I started moving under Gene as he would pull his cock out until the head was barely in and then slam it back in, up to the nuts. This went on for a very long time. Then Gene started moving faster and faster, moaning loudly, those huge nuts slapping me in the ass. Then with a mighty thrust, he filled my ass with sweet come.
The next morning, he woke me up by putting that big thing back up my ass again. This time was even better because I had experienced it before.
When I went into the bathroom to shower, I looked in a full-length mirror on the bathroom wall. I looked like hell. I had hickeys all over me and large, dark circles under my eyes. But I felt great. Gene and I parted company promising to see each other often, which we have.
That night I realized I loved this kind of sex, so I decided to do all I could to become a woman—short of surgery. Since then I have started taking female hormones, had all the hair removed from my face and body and let my hair grow down to my butt. I wear clothes that show off my long legs and round, feminine hips. I now have more boyfriends than I can count. I still pick up men at bars and, when possible, I ride up and down the interstate with the top down on my car, trying to attract truckers. I also stop at rest stops and truck stops and fuck these great guys. Most of them already know I have a very small dick between my great legs, but some of them have had their dicks sucked by me and not known that I am a man.
None of them would have been pissed off, mind you, because I give the best head on the East Coast.—
Name and address withheld
JACK-OFF BUDDY HELPS OUT A FRIEND IN NEED
The following events happened over twenty years ago. This is the first time I’ve told anyone. While you’re reading, please remember that truth is sometimes stranger than fiction.
During our senior year in high school, when we were both eighteen, Allen and I were neighbors and best friends. I spent a lot of time at his house after school because both of his parents worked. He had his own room and he had an older sister with fabulously large breasts who was in the habit of going braless. In time, we became jerk-off buddies, using Allen’s large collection of magazines.
We’d sit side by side on the edge of Allen’s bed with the door locked as we stroked our erect cocks while reading his latest magazines. Allen often reminded me that he admired my cock because it was so large. I had a very thick, six-inch circumcised cock with a large head. Allen had a thin cock barely five inches long with a small head partially covered by his foreskin. What he lacked in cock size, Allen made up for with a pair of enormous, low-hanging balls. He also shot off huge loads of come—about two tablespoons compared with my one teaspoon. I enjoyed watching Allen fill up his cupped left hand with huge loads of hot jism. One time, when I had trouble shooting off, Allen rubbed a handful of his hot come on my cockhead until I shot one of my best loads ever. I really enjoyed the feel of his hot sperm and slippery hand on my cock. Allen realized how much his hot jism turned me on because I practically passed out afterwards.
The next week, Allen came up with yet another way to jerk off. We both sat on his bed facing each other with our legs spread wide. Allen put his thighs over mine and we moved closer until we were cockhead to cockhead, sitting on top of an old towel. We’d shoot our hot sperm all over each other’s organ. Allen always came first, shooting gobs of gooey sperm all over my cock, pubic hair and balls. As his hot spunk covered my organ and dripped down to the towel, I’d shoot my load—aiming at the huge balls hanging low between Allen’s legs. Because I had a longer cock, I was practically touching Allen’s balls when I shot off. I always hit my target.
Allen was a jerk-off expert. He taught me to wait for at least three days so I’d shoot a bigger load, to take a hot bath so my nuts would hang down like his, to fondle my balls before I shot off and to use a greasy finger to play with my asshole. In early summer I managed to get poison ivy on both of my hands and one of my arms. I had to wear cotton gloves on my hands to keep it from spreading. After about a week, I was extremely horny, but I wouldn’t touch my cock with my hands and I couldn’t jerk off with my gloves on. When I told Allen about my problem, he told me to come over on Saturday night and he’d help.
On Saturday night, Allen locked the door to his room and told me I had to smoke hash with him and get high. He dimmed the lights, told me to strip and complimented me on my large penis, as he usually did. I was so horny that my cock had juices dripping out of it. Allen told me to kneel on the floor and put my head and shoulders down on a pillow. I got into position with my ass up in the air as Allen lubricated his hands and began fondling my cock and dangling balls. My cock snapped to attention as he began greasing my asshole. This was the highlight of my life: I was extremely high and my best friend was handling my swollen, throbbing genitals. Allen stretched my asshole with one finger and then with two until I was fully relaxed. Then he put his thin cockhead against my asshole and very slowly penetrated my ass. When his rod was fully inserted, I could feel his warm thighs against my hips, and then he began stroking my greased cock. In this position, gravity caused my balls to hang toward the head of my cock so that he could stroke my cock and fondle my nuts at the same time.
Allen moved slowly in my ass—in deep, then back out. I never would have believed a real cock would feel so good in my asshole. His hips rocked back and forth and his heavy nuts bounced against me. He began to moan, and then he shot a huge load of come inside me. As he blew thick wads of jism in my asshole, I felt a pressure build up in my balls. They drew closer to my body and I knew I was going to shoot an extra big load of come. When I exploded, the first spurt rocketed out and splashed against the bottom of my chin. Allen slowly milked my cock and balls, giving me sufficient time to shoot six hot wads of jiz on the floor. It was the best come of my life, and the largest load I’d ever shot.
For the next three weeks Allen serviced me every two or three days. When the poison-ivy rash completely healed, I paid Allen back by helping him jerk off at least once a week for the entire summer. I enjoyed cupping his long, heavy balls in my left hand as I reamed his asshole with my left thumb. With Allen facing away from me, I’d reach around his hips with my right hand to slide his foreskin back and forth over his glans until he shot his usual huge load of come. Allen would tell me when he was going to come so I could quickly get my left hand in position to catch his hot load. I’d rub his hot jism on my cock until I shot off, too. By the end of the summer I’d become a jerk-off expert. I could get Allen so hot that he’d shoot his first wad of come almost three feet—we had a contest and I measured it.
Today, just thinking about that summer makes my “trouser snake,” now very thick and seven inches long, crawl down my leg and protrude out of my shorts. Honey is oozing out of the slit and my cockhead is throbbing near the bursting point as the poison-ivy summer adventure replays itself in my mental VCR. What a summer that was.—
Name and address withheld
IT ALL HAS TO START SOMEWHERE, AND IT MIGHT AS WELL BE UP THE BUTT
Let me come right out and say it: Being bisexual is the best of both worlds. I have been married for almost twenty years. The two finest sexual things that I can think of are putting my cock in my wife’s sweet, juicy pussy and wrapping my lips around a hard, thick, well-shaped penis.
My wife loves for me to tell her about the experiences of my late teens that helped me discover my bisexuality and my love for cocksucking.
One of my close friends was a stocky, hard-muscled boy who loved to have his cock sucked but would never suck anyone else. The strange part about Chip was, he felt that if you put a dick in his mouth it would make him queer, but he had no problem receiving a blowjob. Gradually he loosened up and began taking it up the ass. This is the story of how I took his virgin ass.
A week after we graduated from high school, we were fooling around in Chip’s bedroom when I asked him if I could suck him off.
“Gladly,” he said. “A hole’s a hole, and I’m horny as hell.” “Great,” I said, “thanks a bunch.”
I lightly licked the head of Chip’s cock and it twitched. I had sucked cock before, and I moaned in anticipation of that thing growing ever bigger. First it was a little small in my mouth, but soon it grew to where it perfectly filled my lips.
Wrapping my thumb and forefinger around the base, I sucked on the top third of his cock while stroking the rest with my fingers. Chip put his hands on the back of my neck and started fucking my face. Soon I could feel his dick going down my throat as if my mouth was one big pussy.
“I’m coming,” Chip screamed, and I was in heaven. When that warm juice started pulsing down my throat, I nearly came in my pants.
When Chip was done, I looked up at him and said, “My turn, right?”
“If you think I’m gonna suck your cock, my man, you’ve got another thing coming.”
“Okay, let me cornhole you, then.”
“You want to stick your dick up my ass?” he asked.
“Indeed I do,” I assured him.
“Okeydoke.”
First thing I did was stick my tongue up Chip’s ass, getting it all nice and lubed. Then I spit in my hand and rubbed it all over my cock. He was very receptive and I shot right inside. My cock was rock-hard, and his ass was so nice and tight that I dropped my load after only a few strokes.—
Name and address withheld
IF YOU CAN’T BE WITH THE ONE YOU LOVE, LOVE THE ONE YOU’RE WITH
Sex with a man had never crossed my mind. When I was single and chasing women, I had been given a few blowjobs by a couple of my male married friends. I could never really understand why they would want to give head to a man when they were happily married, but I didn’t argue. And now that I’m married, I have no need for sex with a man.
One night last week, however, while my wife was away, I went out drinking with an old friend of mine. When we returned to my home, I took him to my guest house. Since we were both drunk, we fell asleep in the guest-house bed.
In the middle of the night, still half asleep, I was stroking my dick to hardness. Something didn’t feel right, however, and when I opened my eyes and looked down, I realized that it was not my own dick I was stroking but my friend’s. He opened his eyes and we stared at each other in bewilderment. Then we laughed out loud. The warmth and texture of my friend’s growing cock in my hand had my cock as hard as a rock.
Figuring he ought to return the favor, he grabbed my cock and started stroking it like I was stroking his. It had been a long time since another man had touched my cock, and I must say that it was refreshing, because he knew what he was doing.
Without hesitation, I leaned over to start an adventure I will never forget. I viewed the object in hand as my own. I lowered my lips around his shaft as far as my mouth would allow, closing my lips around him just tight enough to have the proper pressure.
Then I slowly slid my lips up and down the shaft, feeling the texture of the skin as it slid over the inner hardness. The swelling veins really turned me on. I moved ever so gently over the outer skin with my lips, up and down, up and down.
I stopped occasionally to run my tongue along the shaft to the head of his cock and around the bottom side of his helmet. Then I returned to my up-and-down movements on his stiffening rod. As I went up and down his cock, I could feel his thighs and butt tighten, and then his nectar erupted and shot down my throat. It was great—warm and sweet. His globs were so big that I felt like I was eating raw oysters.
As I cleaned off the subsiding shaft, I realized that my friend was still stroking me off. My rod had never been so hard. With a few more strokes of his hand I exploded like I never had before.
I have come to the conclusion that this form of masturbation can only be accomplished by another man. I still prefer women and so does my friend. We only did it that one time, and then he moved away. But I’d like him to come visit me.—
M.D., Big Sur, California