Virgin No More

Content advisory

:

This story contains references to enema play. While I've tried to tone down the details for readers for whom the topic may be squicky, I had to include it, since this was the actual setting of my defloration. I've tried to avoid the gory details as much as possible and focus on the main event and the profound insight it gave me into who I am. That's why it's in Gay Male instead of Fetish. If you choose to bypass this story, I'll understand. However, I urge you to give it a read: you'll learn more about my own background and, I hope, enjoy the story.

Reader's Note

: Note that the Soma's Journey series isn't chronological. The events of this story took place before several of the others.

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I was browsing Craigslist, looking for a man to tie me up and feed me his cock, when I ran across something completely different. A man in town was looking for someone for enema play with light bondage included. To this point, my entire experience with enema play had been given myself a Fleet prior to inserting a butt plug. I had never cared for bathroom sports, so my initial thought was a hard no. However, I was in a kinky mood and thought it might be an interesting experience (and would clean me out inside), so I replied to his post.

I told him I was new to this, but that I enjoyed bondage play. At the time, I was relatively inexperienced with playing with men. I told him that, and that I had yet to be taken by a man. That seemed to pique his interest and he invited me to a play party he and his friend, both dominant types, were hosting at his apartment in two days. There would be two other men, both submissive, to join in the fun.

I told him I would love to experience enema play, as long as it was safe. He assured me they played safe and that there would be nothing in my enemas except warm water and some salt. He sent me a photo, showing a nice looking man of about 45. Given he was an investment broker living in a newly gentrified area of town, I felt reassured and told him I'd be happy to be part of the party. I had enough time off accrued that I could take the afternoon off with no problem.

He lived in an old mill building, located near the downtown area, that had been converted into loft apartments. I took the elevator to his apartment and was greeted by his friend, who also appeared to be in his forties. He was stocky, but with the look of someone who hit the gym, as his leather chest harness emphasized. He had the look of a business professional, that is, if business professionals wore jock straps, a chest harness and nothing else.

"I'm glad you could come. You're the first; the others will be here soon. Take off your clothes and put them on the sofa. We'll be playing upstairs."

"Yes, Sir," I said, a bit nervously.

I took off my clothes slowly, embarrassed by my own middle age spread and lack of muscular development. When I was naked, I stood in front of him while he walked around me. He tweaked my nipples and gave my cock a rub, which caused it to begin to rise.

He escorted me up the stairs to the loft area, where I saw my host hanging classic red enema bags from IV poles. The next thing I saw was a large king bed. It was covered with plastic sheets and had a headboard and footboard made up of a set of wooden slats. My host was wearing the same chest harness and jock strap as his friend and had the look of someone used to wearing leather. I felt out of place, but his smile disarmed me.

"Since you're here early, you can suck on my cock. Lay down on the bed with your face at this end," he ordered, pointing to a spot to the right of the footboard.

There were two leather cuffs attached to the slats. I lay on my stomach and he attached the cuffs to my wrists. He put a pillow on the top rail.

"Hang you head over this and suck on this," he told me, pulling down his jock strap and showing me a medium size cock nestled in a smooth crotch. I was surprised to find he shaved his crotch, but I didn't mind in the least.

I licked my lips and opened my mouth. He inserted his half erect cock and I started licking on it, feeling it fill my mouth. It grew longer, but wasn't overly thick. I settled into a steady sucking motion while running my tongue over it. Being restrained as I was, I couldn't bob my head much and had to rely on him to supply the motion. He moved in and out carefully, not choking me and letting me taste his precum.

At one point, he turned to his friend. "He's got a good mouth. Want to try it?"

"No, thanks," he replied, in a bored voice.

I was a bit miffed at that, as I was hoping to taste his cock. Besides, it sounded almost insulting that he didn't want me to suck on him. After all, everyone wants to be sucked, right? As I said, I was still inexperienced with men and had a lot to learn about tops.

He took his cock out of my mouth. "That's enough for now. I don't want to blow my load too soon."

He moved behind me and I felt his hand exploring my ass. He ran his finger over my ass crack and watched me shiver when he rubbed my bud.

"Your ass is cherry, you said?"

"Yes, Sir."

"Why is that?"

"To tell you the truth, I'm very tight and I've been afraid someone would tear me and make me bleed. That would be difficult to explain to my doctor."

===

We interrupt this story for a bit of history.

The full truth was a bit more complicated. From early on, I had a strong dislike for my own bodily fluids. While, like most boys, I had learned to write my name in the snow with yellow ink, I had an aversion to getting any urine on my body. And while I had, at long last learned to enjoy the taste of a man's precum and cum, I could only eat it if he ejaculated directly into my mouth.

The thought of a man's cum on my face or chest filled me with disgust. And, to this day, I can't eat my own cum, no matter how much I try. Perhaps if I had the flexibility to suck my own cock, I'd be able to manage it. But, alas, I didn't have the body shape for that. Even my favorite Domme was unable to get me to lick it off my hand.

The few times I had put something in my ass, from the first pencil to my first butt plug, it had come out with that distinct smell and telltale brown streaks. I had managed to avoid throwing up, but I was mortified at the prospect of a play partner encountering the same foulness.

"That's really whack!" Indeed, it is. I've never claimed to be anything other than a messed up person trying to figure himself out. My sexual adventures were, in large measure, designed to help me understand myself and to overcome those childhood inhibitions.

We now return you to the story, already in progress.

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"Don't worry, I'll take good care of your ass. After you've had a few bags, you'll be open and ready to take me. I like showing virgins what they've been missing."

He was pushing all the right buttons. Several times recently, when playing with a man and feeling him rub his cock over my ass, I had the desire to say, "Please, Sir, take my ass." However, I had always chickened out. Would today be the day?

"Your cock looks like the perfect size for me, Sir and I really want to feel one in my ass."

"I'll wear a condom and go easy on you. And don't worry: we keep plenty of lube here."

"Thank you, Sir," I replied, not thinking over the implications of that statement. "I'd like that. Could you do me two favors?"

"Sure."

"First, could you blindfold me now and keep me blindfolded while you play with me? It helps me get in the mood."

"Sure, I can do that."

"Thank you, Sir." I saw his friend was frowning, probably wondering what kind of flake I was. "One other thing: could you take a picture of your cock in my ass? I'd like to have a copy to look at."

He smiled. "I'd be happy to take a picture. I'll get my camera."

"Thank you, again, Sir."

He didn't have a blindfold handy, which surprised me, but he found a hand towel and tied it around my eyes. It felt a bit awkward, but it provided the anonymity I needed. I didn't want to connect my experience with actual people, just abstractions. I thought that, in some way, that made it a less gay experience. At the time, I was still not completely convinced that I was anything but a kinky straight man.

I heard the doorbell ring and realized the party was about to start in earnest. Sure enough, I soon heard more bare feet walking up the stairs and the bed creak as another person got on it.

My host uncuffed me and told me to turn with my head facing the headboard.

"Get on your knees, arms out and ass up. Since this is your first time here, we'll start you with one bag. I change nozzles after every bag to keep things sanitary."

After assuming the position, I felt his gloved finger rubbing lube on my anus and entering me slightly. I jerked slightly as he inserted the nozzle in my ass and pushed it inside me.

"I'm going to open the valve now. Don't move until the bag is empty. I'll let you know."

And then, I felt my ass start to fill with warm water. It was a pleasant sensation. From the movement to the right of me, it seemed someone else was getting the same treatment. I heard the sound of flesh slapping flesh followed by a grunt and figured someone was getting their ass smacked.

Meanwhile, I was filling up and started feeling pressure in my rectum. A hand rubbed my stomach gently to encourage the flow of the water.

"Almost there. Now, when I remove the nozzle, hold it in. You'll feel some cramping, but ride it out. Let me know when you can't hold it in any longer. I'll check with you in fifteen minutes."

Several years before, I had been given a barium enema as part of a proctological exam, so I had an idea of what I was in for. I had held that one in for what seemed like half an hour, so I was confident I could handle this with no problem.

I lay my head on my arms, turning it toward the person I could feel weighing down the bed to my right. I heard the sound of the plastic sheet rustling and the soft moans of a man in pleasure. My bedmate appeared to be enjoying his treatment. I heard a slight gurgling as the water continued its invasion of my colon.

Time passed. Occasionally, a hand would reach under me to rub my belly and squeeze my cock. I longed for a cock to fill my mouth, but none was forthcoming. Not knowing the protocol for these events, I didn't want to ask for one. Instead, I focused on the sounds and smells around me. So far, the smells were neutral. From downstairs came the sounds of...Peggy Lee?

The cramps began. I shifted my ass to try to ease them. A hand appeared and rubbed my back, then my belly.

"How are you doing?"

"I'm OK, Sir. A little cramping, but nothing I can't handle."

"Good. Let me know when you need to expel your load."

The bed creaked and I felt it lighten. Apparently, my companion hadn't lasted as long as me. I took a bit of perverse pride in knowing that I had better bowel control than he did. As if to punish me for such thoughts, a major cramp had me pressing my head down and raising my ass, trying to provide as much room for the water as possible.

I focused on keeping my buttocks clenched, willing the water to stay inside. At last, the pain was too much, and I said, "Sir, I can't take it any more."

"You held it for almost thirty minutes. Not bad."

He guided me off the bed and walked me to the bathroom. Once the door was closed, I took off my blindfold so I wouldn't miss the toilet. The smell told me I wasn't the first to get relief today. I turned on the fan, sat down and relaxed. I sighed as the pressure was relieved in a gush of water and less savory materials. As soon as the first wave passed, I flushed and waited. Soon enough, the second gush came out.

I was mortified: even though I knew this was a part of enema play, I dreaded the moment when the next person entered the bathroom and knew what I had done. I suspected the smell was part of the fun for the others, but it filled me with shame...shame for not having full control over my purely natural bodily functions and shame for having allowed my lust to put me in this situation. But at this point, I had no choice: I was here and I was committed. I would see it through to the end. No matter my guilt, I refused to let myself look like a wimp to these strangers.

I was on the toilet for over twenty minutes, expelling the water. At last, the gushes stopped and I began cleaning up. They were prepared: a large box of wipes sat on the back of the toilet. I made copious use of them, throwing the used ones in a closed garbage can thoughtfully placed near the toilet. After washing my hands thoroughly, I replaced the blindfold and opened the door. A few seconds later, my host took my arm and led me back to the bed.

This time, I was on my back. He spread my legs and cuffed my ankles to the frame. Once more, I felt the nozzle enter me. This time, it seemed to go further. Again, the flow of warm water started filling my rectum. The flow was much smoother, not encountering as many obstacles as the first time. Toward the end, I felt my belly start to bloat. He rubbed it as the cramps began; they were not as intense as earlier.

"You took that well. I think you have room for another bag."

I inhaled deeply. One bag had me cramping and in extreme discomfort. What would a second infusion of water do to me? And yet...he hadn't asked me if I wanted it. He told me what he intended. In my current situation, I didn't have much of a choice. Besides, I had wanted to experience something new, hadn't I? And if it got really, really bad, I had ways to get rid of the excess.

"Whatever you think is best, Sir," I said.

"Good boy." He switched nozzles with a speed that surprised me, and I felt the renewed rush of water. Surprisingly, I also felt a hand brush my arm. I turned my head to my left and felt the presence of another man on the bed next to me. I brushed his thigh shyly with my fingers, then felt him squeeze my arm and relax. At the same time, the bed started rocking and I knew he was enjoying the same pleasure that would soon be mine. I heard the sound of skin slamming into skin and the squishing of....

...the squishing of? That was a new one for me. It couldn't be, could it? The spray of warm droplets on my thigh confirmed my speculation: he was still filled with his enema while he was being drilled. He cries of pleasure told me he didn't mind one bit. Strangely, I felt my cock start to respond to the sound. I resisted the urge to grab it. Instead, I forced myself to lay still, only occasionally stroking his arm.

Meanwhile, my gut was beginning to complain in earnest about its treatment. The cramping grew stronger and I had to strain hard not to expel anything. My enema Dom was massaging my belly, distributing the water more evenly.

"You should see yourself: you look like you're pregnant. I'll bet you could take a third bag...stop shaking your head. We don't have time for that today. But, next time, we'll take you up to three bags. You're a very good boy. Now, I'm about to pull out the nozzle. Don't let anything drip out...there we go. You look nice all filled up. Just lay there for a bit and I'll let you up when I'm ready."

The cramps were a new part of my existence. I wondered if this was what PMS felt like. If so, I was glad not to have to worry about that. I touched my belly gingerly and knew he was right: I must have looked like I was in my third trimester. The cramps were growing more intense, but I could do nothing but pull on the leather cuffs securing my ankles to the bed. To my left, I heard a growing duet of cries of pleasure, followed by a gurgling sound. Then, silence and the lightening of the bed.

I was alone with my thoughts and my growing agony. Peggy Lee was asking if that was all there was; I hoped it wasn't. Above all, I didn't want to humiliate myself by leaking on the plastic sheet. I focused on my breathing, trying to move away from the pain.

An eon later, I felt hands loosening my ankle straps, then the voice of my host.

"I think that's long enough for your first time. Let me help you up...careful! I don't want you spilling anything on the floor. Here we are, back in the bathroom. I hope you don't mind the smell; it's been a busy afternoon." He laughed and closed the door.

I took off the blindfold and inhaled deeply and rapidly, not because I enjoyed the stench, but because I wanted to overload my sense of smell and shut down the receptors as quickly as possible. I had no time to waste. I dropped onto the toilet seat and relaxed my sphincter.

I won't go into detail on the next half hour, except to say I hadn't realized how sensitive the tissue around my anus actually was. That first rush of water was pleasurable, almost orgasmic. I also hadn't realized the sudden release would exacerbate the cramps. I was doubled over on the toilet wondering if my anus would ever stop aching. This was a new form of pleasure/pain for me.

I found that rubbing my belly and massaging it downward would trigger a new round of gushing. I was flushing as quickly as possible, terrified the remnants of the enema would overflow the toilet. And, of course, at the end of each flood came the sound of air being expelled. Normally, I would do anything to avoid any sort of gas release in public. Here, I was helpless to stop the sounds; I prayed to Peggy Lee to sing louder...

All things must come to an end, and, finally, the last spray came out. I waited...nothing, I pushed down on my belly...nothing. I pushed my rectum to the point of herniating ...nothing. I was clean...on the inside.

I stood up carefully and, after wiping down the toilet, used up another stack of wipes cleaning my ass, making sure my cheeks were clean and my crack was spotless. After washing my hands thoroughly, I put the blindfold back on and opened the door, my cock rising in anticipation of what was to come.

"I'm ready for you, Sir," I said with more certainty than I felt.

"And I'm ready to make that ass mine."

He took my arm, led me back to the bed and positioned me on my back with my head over the edge. I didn't know if anyone else was still around, but I didn't care. He spoke to me.

"Last chance. Are you sure you want me to do this?"

"Oh, yes, Sir," I replied breathlessly, "I'm ready to lose my virginity. I want you to take my cherry."

"Good boy. Get me ready," he said, rubbing my lips with his cock.

I opened my mouth and took it in. I licked and sucked it and felt it swell in my mouth. It was growing uncomfortably long, but wasn't as thick as mine. I relaxed a bit: it didn't feel like it would tear me. But I wanted it all in my ass. I wanted it to fill me up.

When he was fully erect, he withdrew from my mouth and climbed onto the bed. He pulled me up so my head was on the mattress. I heard the sound of a condom wrapper being opened and relaxed a bit more. Then, I gasped as I felt a slick finger rubbing the sensitive tissue around my anus, then penetrating my opening slowly and gently. The initial entry caused me to buck, but he rubbed my stomach comfortingly and I relaxed more and let him push his finger further in.

He slid his finger in and out, slowly picking up the pace, and I responded. After a brief burning sensation, the gliding motion became warm and soothing. I could feel my cock responding. He must have seen that, because he slid his finger out and, after a moment, returned to my virgin channel with two freshly lubed fingers. They slid in more easily and he added a twisting motion to the action. I started to mewl and raised my buttocks to encourage him to go deeper.

"Please, Sir, take me. I need you to take my ass. Please, make it yours."

His fingers withdrew and he pushed my legs up onto his shoulders. I felt the tip of his cock poised at the entrance and I held my breath. It felt like the head was in firmly. While I was adjusting to its presence, he put his hands under my knees and pushed me forward. At the same time, his cock slid into me and I cried out in a high pitched voice, but not from pain.