The First Time

Some are going to read the title and think this story is about losing virginity. Instead it is about the first time that I got Terry fucked by another man. Truthfully it turned into a small gangbang, but now I am getting ahead of myself.

I should begin, though, with a description of Terry I suppose. Terry is 28, 5'8", 35C tits, and rounded curves in that wonderful hourglass shape. She works out every other day, so she's not bulked up or a hard body but she is well toned. She has shoulder-length blonde hair, hazel eyes, and a smile that lights up the room when she flashes it.

Terry is also almost terminally shy. Considering how good she looks, and how much I enjoy showing her off, this was an obstacle to be overcome from the beginning. Considering how much I love seeing my lovers' faces in the throws of passion – and occasionally getting sloppy seconds – it was something of a disappointment too. One on one though, Terry was a sexual creature and when she found out about my kinks, she agreed that if we could ever get her past that shyness, she would not mind. Like I said, it was a challenge.

At first I just tried to get her to dress in some revealing clothes when we would go out. After nearly a year, the best I got her to do was wear a few low cut tank-tops with shorts. Oh that was frustrating for me, but we clicked so well in every other way there was no way I was going to let her reluctance end things. It did leave me wondering if that side of my sexual adventurousness was at an end though.

I have no idea why it occurred to me, but it finally did, that she had agreed to go along with my getting her fucked by another man if I could get past her shyness. As I also said, she did have a certain level of adventurousness, so I had gotten her worked up in public before, when we were where "no one could see." All of which led to the formation of a plan.

Two months after the thought occurred to me, we were planning on being at a science fiction convention in another state. If you have ever been to one of these conventions you are aware that a fair amount of sex goes on behind the scenes. I decided to take advantage of that. We had our own room after all; we were in another state, and so there was little issue with someone back home finding things out. The setup was perfect.

For the first day I let things go no further than an aggressive and large amount of sex between ourselves. In fact we did not leave the room the day we arrived, but we were there a day early so it did not matter. I did push her boundaries a little by ordering a pizza for supper. I did not tell Terry though, and in the thirty minutes I made sure that we had just finished a heated round of sex, kicked the blankets off the bed, and made sure they were across the room. Get them knotted up and it is amazing how far they will fly. Anyway we are cuddling in the afterglow when there is a knock on the door. Before she can move, I am at the door, opening it, and inviting the guy in. Terry dove for the covers, but then just squeaked and flattened out on her stomach. The end result is that the delivery guy still got a definite eye full of Terry's gorgeous body. That is as far as things went though, but I am still betting the guy considered it a good tip.

Amazingly it did end up loosening Terry up, which just fell right in with my plan. How did it loosen her up? For the first time ever she agreed to go braless under one of those tank tops. I was stunned, but also ecstatic!

So there we were on the second day, the first of the convention, and Terry was going braless under a low-cut tank. I was in heaven. I also took shameless advantage of the situation. Every chance I got I caressed her tits, pinched her nipples through the top, rubbed her ass, and pressed against her back to rub my hard cock over her ass too. All of which I knew would be driving her crazy. It was a perfect scenario.

What Terry did not know is that I was watching the guys that really started looking her over. When I finally saw one that was about my build and size, I slipped away from Terry, and made my way over to the guy.

The conversation was short and to the point. I asked if he liked what he saw, asked if he would like the chance to fuck her, and then arranged a meeting time outside our room. Yes, I was going to be a bastard. After the conversation though, the guy turned up nearby several more times, not that I could blame him, especially when I started making sure he could see when I would grope her and make her react. Two more hours and I think they were both about to pop.

It was Terry that brought things to a head, almost on schedule. I was pressed up behind her, rolling both nipples with my fingers. She was worked up enough to be moaning at this and finally husked into my ear, "If you don't stop, we're going to have to leave for the room so you can fuck my brains out."

I just smiled and whispered back and whispered, "What do you think the point has been?" She moaned, turned to stare into my eyes, and licked her lips. "Go up to the room, strip, turn out all the lights and draw the curtains, and start using your toy. You can't cum though. I want you hot and ready to cum the moment my cock rams into you." Her eyes closed and I could see her shiver, but she nodded. It was similar to a game we had played before, so she took off without me, figuring I would be behind her in a few minutes.

Five minutes after she left, I went up to the room too. Sure enough, the "friend" I had made was waiting outside the room. Before I opened the door I went over the rules. First, he had to be bare. She would be tipped off if a condom was used and I did not want her knowing it was not me fucking her until he was buried in her to his balls. Two, do not expect it to happen again. All of which he agreed to readily.

With that, I slid in the keycard and let him in. The moment the door opened we could hear that Terry was more than ready. She was moaning and panting loudly, "Oh god! Oh god! Please!" No one was there and she was still begging with the need for release. I just smiled and waited for the sound I knew would be coming. Why sound? Because she was a good girl and the lights were out. It was dark in that room.

Then she made the sound that I had been waiting on: that low throaty groan that told me a cock had just drilled her. I had only heard it when it was my cock sinking into her body, which made it all the more wonderful to hear now that I was not...otherwise occupied myself. Anyway, I was just about to press into the room and flip on the lights when the first unexpected event for me occurred: two guys showed up. Colin, the "friend," had told them what was going on and they had come by to see if they could get in on things. For a second I got angry, but then did a mental shrug and said, "What the hell?"

"Sure," was my reply as I pushed open the door fully and flipped on the light. The timing could not have been better. Terry was screaming and panting in the throws of a hard orgasm. Which meant even with the shock of the lights coming on, there was no way she was going to stop riding the cock that was in her.

The sight was amazing. Terry's favorite position when she is really horny is doggie. So there she was on her hands and knees on the bed, Colin behind her gripping her hips so he could pull her back into each savage thrust he gave her. Her eyes widened when she saw me, so I know it registered in her mind that someone else's cock was fucking the hell out of her, but she just could not care at that moment.

The other two guys were already stripping down. About the time Colin shot the first load of cum into her pussy, there were three more naked guys ready to go. I moved off toward her head and told her, "Turn your ass for the next." Still moaning and shuddering in the aftermath of an intense orgasm, Terry did not hesitate.

She swung her ass around to point toward the other two guys and then dropped her head down to gobble up my cock. Colin was stretched out watching the rest of us while one of his buddies moved in behind Terry and sank his cock into her. I will say that none of them were as thick as I am, but this guy was probably an inch or two longer, and it was an amazing feeling to have my cock down her throat as she started to shudder and moan as he forced his full length into her. She whimpered softly, so I know he bottomed her out, but she was still grinding back onto him. She wanted more.

I watched as his cock started pistoning in and out of my lover. I figure he lasted for five thrusts, and he still lasted longer than I did. Even while pouring my cum down Terry's throat, I saw the guy about the pull out and quickly reached around to grab his hips and jerk him back into her as deep as he could go. I held them together like that, making sure his seed shot all over her cervix. My own softening cock was driven down her throat because of it and she moaned in another orgasm at the feel of hot sperm spewing inside her.

When I pulled out of her mouth, Terry grabbed my hand and pulled me down to whisper fiercely and excitedly in my ear, "God! You're letting them cum in me!"

I smiled as the second guy to fuck her pulled out and whispered back, "All three of them in your pussy...everyone but me. I'm going to keep cumming in your mouth. Now turn to let the third mount and breed you."

As unnerved as pretty Terry was at having three strangers fill her cunt with sperm, she also showed how exciting it was to her by immediately repositioning with a groan and shudder so the third guy could shove his cock into her pussy. He too came quickly. What guy would not be excited as hell by seeing a gorgeous woman having the hell pounded out of her pussy? He also tried to pull out, but I had moved where I could see every movement of his cock in and out of Terry. I moved in behind him, grabbed her hips and pressed him forward. "Everybody cums in her pussy the first time," I announced and Terry groaned like a wanton whore. I was in heaven I have to say. I moved back from the guy to let him finish his business in Terry and found a chair.

All three or our new friends needed some recharging time, but they did not leave Terry alone, and pretty much forgot that I was in the room. She writhed and moaned for them as their hands, fingers and mouths roamed and explored every part of her. Her tits were kneaded, nipples twisted and sucked. They even kissed her fiercely which did excite a little jealousy in me, but that is part of the experience too.

When I saw that the guys had started to recover, their cocks finally starting to get hard again, I said loudly enough to be heard over the moans, "I want to see her double penetrated." Terry stared at me in horror, but the guys were already moving. One guy was on his back and the other two moved her over him and before she could protest they had impaled her on him. She shuddered and still tried to fight free, but by this time she was held in place and one of the others was moving in behind her.

Now Terry and I had had some furious fuck sessions while discussing the idea of having her double-penetrated. The idea would have her screaming and riding me like a wild woman. This is why I even suggested it: it seemed something she at least wanted to try. Talk of it certainly sent her into frenzy.

That said, I thought at first that I had made a mistake. When the guy behind her started pushing his cock into her ass, she screeched, and not in the good way. Concerned I stepped forward and said, "Guys, careful! She's not done this before!" They were excited and clearly just wanted to get at fucking the hell out of Terry, but they winced and nodded, slowing down.

Terry was panting and whimpering, "It hurts. Oh god it hurts." I moved closer and leaned down to whisper, "You want them to stop then?"

She clearly thought about it, but then shook her head and gasped, "Let them get all the way in at least." I nodded and proceeded to watch as the guy in her ass slowly eased the rest of his cock into her tight ass.

I started to leave it at that, but had another brainstorm. Leaning down I whispered into the guy under her, fucking her pussy, "Fuck her. Start slow, but get faster." The change was pretty dramatic. Terry gasped when the cock in her pussy started moving in and out of her again, but then gave a groan that had nothing of pain in it. As the guy below her started picking up speed, her body reacted and in just a minute or so she was starting to rock with him.

There was no way for her to do that without fucking herself on the cock in her ass too. She alternated between those moans of ecstasy and those of pain, but as the guy fucking her picked up speed, so did she. Finally the cock in her ass started fucking her too. How could he not? The pace picked up further and Terry started throwing her head about and hissing, "God it hurts, but it feels so damn good! Never felt this full!" That cut off in a moan after which she announced, "Fuck me! Oh god make me cum!"

Being the perfect gentlemen that they were, they obliged. With a good rhythm both started pumping their cocks into her. I moved back to my chair and as I did the guy I had actually invited moved to Terry's face and shoved his cock into her open mouth. She gobbled him up and for the next five minutes I got to watch as my girlfriend was quite thoroughly used in all three holes.

As often happens, all four of them came at about the same time. Terry's noises were muffled thanks to the cock in her mouth, but she told me later that it was incredible feeling all three cocks suddenly swell and start flooding her with sperm. She loved it!

Sadly, she threatened my life if I set anything like that up in what remained of the convention. She also admitted later that she was not sure if she could do that again as she was still shy. Not that I stopped trying to convince her mind you, and I have to say she got much more daring about what she would wear out afterward, and as you can imagine, she came around to my way of thinking after awhile.