Anal Engagement

How far would you go for a man you loved, girls?

Let me make it a little more difficult. Or simpler. How far would you go for a man you had loved for ten years, but hadn’t seen for five, when you were finally in his arms where you belonged. What would you do to show him you loved him?

Me, I had thought my virginity would be enough. I wasn’t completely innocent. I had given my boyfriend while Mr. Wonderful was gone handjobs and blowjobs and he had felt me up and fingered me. But, I had stopped him from going all the way. I was saving myself for marriage.

At least, that is what I told him. I think it is even what I told myself for awhile. When the truth dawned on me, that I could not give him that last bit of myself because Mike was still in my mind, I broke off my engagement to Cory. It startled my family, because he and I had been together since… well, since that summer. That summer when Mike dropped off the face of the Earth.

I was fifteen and he was eighteen that summer. We were at a going away party for his best friend, Jack. Jack’s dad was my pastor and he was moving to a church in Colorado. I hadn’t fully wrapped my mind around the fact that I wasn’t just losing Brother Tommy and Jack, I was losing Mike too. If I had, I might have let him go further than just playing with my boobs while we kissed. But, I didn’t. And then he was gone.

But, I was a stupid girl then. Five years later, I was twenty, would graduate from a junior college in December, and was going to start classes at the major university less than thirty minutes from where his mother lived in the spring. While Melinda and I were visiting the school, setting up my classes, she talked me into calling him. I thought my heart would break when his mother told me he had graduated that summer and moved away. Then she told me where.

A police cruiser stopped to make sure everything was all right when I screamed. I was laughing and crying and babbling nonsense, but Melinda managed to convince them that everything was okay. After they left, she started screaming and laughing and jumping too when she finally figured out from my insane chatter that he had moved to the exact same town my sister lived in, less than thirty minutes from my grandparents, where my family spent every holiday. Where we would be going in two weeks for Thanksgiving. And he was right there.

Thanksgiving was… very different that year. I was late because I had called him and he had told me where he lived. I went over to visit him and things got extremely out of control. At the time I should have been sitting down with my family to say a prayer of thanks, my shirt was on his floor. I don’t know how I managed to keep my pants on, or how I managed to finally tear myself away to dress and leave, but I did.

The next weekend, after church, we were gathering in the fellowship hall. I heard sixteen year old Beth Winger scream and she went flying across the big room. We all tracked her progress as she all but climbed some guy like a squirrel climbing a tree. It wasn’t until Melinda yelled “Mike!” that I realized who the little hussy was molesting.

Mike was laughing as he set Beth back on her feet. My heart couldn’t decide whether to stop or flip right out of my chest as I stood frozen and staring where I had been serving potatoe cassarole. Mike pulled back and looked at the girl and everyone could see he had no idea who it was who was mauling him in a church.

“It’s me, Beth Winger.” She beamed up at him.

“Hey, monkey face!” Mike laughed. “I haven’t seen you since you were eleven. You’ve grown up while I wasn’t here.”

I think poor Beth could have died right there. She had always had a major crush on him. I would have felt sorry for her, but she was so beautiful, and rich, and she had a voice the birds would envy when she sang. All the boys were sniffing around her. And there was a voice in the back of my mind screaming “Mine, bitch!” Not very Christian of me, I suppose. But, this was Mike. Mike!

“What are you doing here?” Beth asked. “Oh, it’s so good to see you!”

The little minx hugged him again, plastering that firm, young body right against his. I stumbled two steps and turned to look at Melinda who had just given me a hip that nearly put me on my face. She mouthed the word “Go”.

“I came to see Esther,” Mike was answering her. And, pulling away from her a little, I might add.

(Don’t you dare call me Esther. You have fair warning. Only he and my Dad have ever called me by my first name. Everyone else calls me Janine. Don’t make me hurt you.)

Beth’s eyes turned towards me as my feet seemed to float a good two feet off the ground. Oh, it was glorious. That look on her face. The idea that he was here to see plain old me instead of her. I would have revelled in it, but I was too busy. I mean, he was here to see me. He had driven three hours to see me. He had come to me.

I’m not really sure about what happened the next month. I do know we saw each other every weekend and talked on the phone every weeknight. I know he gave me a one karat engagement ring for Christmas, but told me and my folks that there would be no wedding until I graduated.

On Valentine’s Day, we made love for the first time. I hadn’t expected my first time to be so amazing. I mean, I had heard horror stories about how much it hurt. In a way, that is why I did it. So that I wouldn’t have that pain on my wedding night. But, he was amazing. He took his time and gave me orgasm after orgasm, not entering me until I was nearly out of my head with need and desire. Then, he had me on top, and he did this thing with his thumb against my clitoris while I was taking him in. Oh, it was wonderful.

But, things changed. It was the past that caught us. Why would my relationship with Cory bother him so much? I mean, his two engagements and several girlfriends didn’t bother me. Well, not much. Well, I didn’t say anything about it anyway.

In fact, it was the fact that I was going to Cory’s wedding that brought it all to a head. I was going to see my ex-boyfriend get married instead of coming to visit him over Spring Break. They had scheduled the wedding then so that I could come. If he had tried to forbid me to go, there would have been one hell of a fight. If he had asked me not to go, I would have gone anyway. But, he didn’t. He just told me that he understood and he would see me some other time.

It was something in his voice. A sadness that was almost palpable down a phone line that haunted me as I was driving towards that wedding. It seemed natural that I should take the exit that led to him rather than continuing on down the highway to that wedding.

“Esther? What are you doing here?” Mike stood in the door wearing nothing but a pair of shorts. Sweat was streaming down his chest.

“You don’t want me here?” I asked as I stepped forward and ran a finger through that wetness coating him.

“Yes.” He said, pulling me against him and lowering his lips to mine. “Always.”

I pushed him back a step and once the door was closed behind me, I fell to my knees and yanked his shorts to his ankles. I can still taste the sweat coating his cock, can still smell the muskiness of him filling my nose. I didn’t care. I was here, and from the feeling in my throat he was happy to see me.

Two hours later, my clothing made a trail from where his shorts sat by the door to the shower where we had made love. Two towels lay on the floor next to the bed where I lay in his arms. I had climaxed twelve times and had made him cum for me three. I could have happily gone to sleep right there in the arms of the man I loved. Damn it, why couldn’t I have fallen in love with a man who rolled over and fell asleep?

“When you were seeing Cory, what did you two do?” He asked.

“What do you mean?” I asked. I knew he had known I was a virgin. During that magical first time and several times before he had touched my intact hymen with his fingers and tongue before stretching it and breaking it with his magnificent dick.

“I know he didn’t actually put his dick in you. But, well, you guys were together for four years. You were talking about getting married. I assume you did more than kiss him.”

“Hey, fiancee mine.” I poked him in the ribs with a smile and turned my head to look up at him. “If this is jealousy or something, let me remind you that unlike some people in this bed, I was good.”

“Well, I was told I was pretty good myself.” He grinned smugly.

“Hey!” I swung my leg over his and set my hands on his chest. “Talk like that will get your little willy superglued to your leg.”

“You won’t do that.” He kept grinning. “You would miss it too much. Or don’t you think I’m good? I can try something else if you aren’t satisfied yet.”

“Oh, God,” I moaned as he raised up and kissed my neck. “You’re trying to kill me aren’t you.”

“I don’t think it’s possible to die from too much pleasure.” He murmered as he turned us over so I was flat on my back while he continued kissing me. “Let me show you.”

“Make sure they put ‘she died smiling’ on my tombstone if you are wrong,” I panted as he kissed his way down a line between my breasts to that magical place between my legs.

He liked to tease me by writing with his tongue and making me guess what he wrote. He joked that when he stuck his tongue in me, it was punctuation. Side to side was a question mark. In and out was an exclamation mark. Oh, the things he could do with that tongue. He couldn’t lick his eyebrows, but he could touch it to the tip of his nose. And he didn’t have a little pug nose either.

But, that wonderful tongue wandered somewhere it had not before that evening. I squealed and jerked my hips as I felt it lick lower, around my sphincter. I opened my eyes and saw him grinning at me from between my legs. Before I could tell him not to do that, he was back at my clitoris, sucking and licking and kissing. I was approaching that magical “o” moment again, when once again, his tongue swiped low and touched me there again.

It was strange. I had never even imagined that someone would touch me or lick me there. If you had told me I would let them six months earlier, I would have slapped you. I honestly can’t say that I liked it, exactly. But, with his head between my legs, lapping away at me, first around and between my vagina, then that inch of skin between, then around the tight pucker of my sphincter, I wouldn’t have dreamed of asking him to stop. I was close. So very close. I caught my legs in my hands and spread them high and wide to give him better access. Just a little more. Just. A. Little. More.

I came screaming when his tongue slipped inside my ass. It might have been his nose bumping my clit. But either way, it was the best fucking orgasm of the night.

“So,” he grinned down at me when the wave of bliss passed. “Did you ever let him do that?”

“Mike,” I groaned. “Do we really have to talk about this right now? Can’t you just, I don’t know, hold me while you fall asleep or something?”

“But, I’m not sleepy. Not yet.”

I screamed and wiggled until I almost fell of the other side of the bed trying to get away from his fingers as they pressed into my pussy.

“Oh, God no. Please no.” I panted, clutching at his strong arm. My feet were sideways, pressing against the wall. “I can’t take any more right now. Please, stop.”

“Ve haf vays of making you talk.” He said in a corny fake german accent. “Tell me vhat I vant to know or they vill hear your screams for miles.”

“Okay! Okay!” I squealed, my feet now planted on the headboard since I had managed to spin a complete one eighty. “Let me turn back around and I’ll talk.”

“Nah, I like the view.” He grinned down at me, holding me like that. “Besides, this gives me better access in case you decide to clam up on me.”

“Fine.” I giggled at how lewd and ludicrous I must have looked if anyone could see me. “What do you want to know?”

“Everything,” he shrugged. “What did you do with him?”

“Well he took me to homecoming every year. Awk! Stop! Stop! I’m talking. I’m talking!”

“That isn’t what I meant and you know it.”

He wasn’t smiling any more. That scared me a little. I mean, I knew he wouldn’t hurt me physically. But he could kill me with a frown.

“Why do you want to know? I’m with you now. And I’ve done more with you than I ever did with him. You know that.” I raised up on my elbows to get a better look at his face. “I mean, you’ve done more than I have with other people.”

“That’s… sort of the… problem.” He finally managed to get out.

“I don’t understand,” I said. And I didn’t. I just knew that this conversation was really scaring me.

“Ok, look. Everything that we’ve done, I’ve done with someone else.” He said. “And everything that you’ve done with someone else, you’ve done with me.”

“And more.” I interjected.

“And more,” he nodded. “I guess, what I’m trying to figure out is how much more. I mean, did you ever give him a blowjob?”

“Um, well. Yes.” I was mystified.

“Did he ever go down on you?”

“Er, no. I always kept my pants on.” I said. “But, I did let him put his hand down them.”

“Ok, so he never touched your pussy with his tongue or his cock. Just his fingers.”

“Um, yeah. Pretty much.”

“Do you like it when I do?”

“Do you even have to ask?” I grinned and reached for him. My grin died when he pulled away.

“What I mean is, do you do these things… do you let me do these things because you like them or to give me something special. Something you haven’t given anyone else?”

I sat up and turned to look at him. Something was wrong, but what it was I couldn’t grasp.

“I don’t know.” I stammered, wondering why men didn’t come with an instruction manual. “Some of both, I guess.”

“Am I good?”

“Sweetie, this is a damn strange way to get a compliment.” I smiled, thinking I knew where this was going.

“I’ve had compliments from women.” He waved one hand, but it felt like he had punched me in the gut. I couldn’t breath. “I want to know if all that practice made me good for you.”

“Oh, thank you so much.” I sputtered angrily. “Now, I’ll never be able to let you fuck me without thinking about the other women you ‘practiced’ on.”

“Don’t you see? That’s my point.” He tried to gather me in for a hug, but I wasn’t having any of it now.

“The only point I see is the one on your head.” I rose from the bed and stormed into the other room. If I dressed and got on the road now, I could still be there in time for the reception.

“Look,” he followed me in from the bedroom as I grabbed my panties and began pulling them up my legs. “What I’m trying to say is that everything I’ve done with you, I’ve done with someone else.”

“Yes,” I hissed as I sat down with my pants in my hands. “You’ve made that very clear. I’m sorry me keeping myself a virgin is such a disappointment to you. I mean, how can I keep up with someone so practiced.”

“That’s not what I meant.”

He slammed his head back into the doorjam so hard it startled me. I froze and watched as he slid down until he was sitting. He was crying. Well, good. I was crying too. Asshole.

“What I meant was, there are things I haven’t done with anyone. I would like to, maybe, do them with you. So that I could have something that I’ve only shared with you also.”

“Oh, sweetie.” I dropped from the couch to my knees and crawled to where he was leaning. My heart ached. “It’s okay. I love what you do to me. It’s okay that..”

I trailed off around a lump in my throat as I tried to assure him it was fine he had done everything with other women that he had done to me.

“It’s the past,” I finally said, as I held his head to my bare breasts. “It’s in the past. We are together now. It’s us now. And forever after this. Or else.”

“I know, I know.” He laughed and pulled back a little. “Or else you’ll superglue my dick to my leg.”

“Damn straight,” I murmered as I kissed him.

As we often did, we ended up back in bed. And naked. And whether I was under him or riding him, I was writhing in pleasure. In the event, I was on all fours with him behind me as he held my hips in his strong hands. I had one hand pushing against the wall, pressing back against him as he pounded into me. My poor abused pussy was wailing it’s way to a fourteenth orgasm as the room filled with the sounds of our grunts the slap-slap-slap of his hips making my ass bounce.

I think that’s why I didn’t notice when his hands moved from my hips to caress my fleshy cheeks. I didn’t notice when they pried them apart. But, his thumb… that same damn thumb that had worked my clitty so good when he broke through my hymen… When that thumb touched my wrinkled rosebud… That, I noticed all right.

I screamed and lost my balance as both the hand holding me off the bed and the one pressing against the wall slapped back towards the strange sensation. I fell foward, with my chin on his pillow. He slammed forward into me. I thought he had filled me before, but with this new position he hit further inside me than he had ever reached.

I fought to scream but could only gasp as the pillow constricted my air. I struggled to get some room, pressing against the pillow with my hands as he thrust mightily into me, pressing me further and further down on that pillow. The orgasm that had been wrenched away from me by the invasion of his thumb crashed through me. I whimpered as I felt his thumb slip inside my sphincter. But, I was powerless to stop it. I didn’t want to stop it as wave after wave of pleasure cascaded through me.

I felt so incredibly full. God, he could have asked me if he could slit my throat and I would have just nodded. So, when he pulled out and said what he said next, I did just that. I nodded yes. I felt so empty. I just wanted to be full again. I nodded. I would have said yes to anything just to feel him again. I nodded yes. Yes.

“I’ve never been inside anyone’s ass.” He whispered as he pulled out of me. “Will you be my first? Esther, will you let me fuck this wonderful ass?”

God help me, I nodded.

The only reason I didn’t scream as he pressed the head of himself into my tight sphincter was because I couldn’t breath. It felt like my eyeballs were screaming for me. Just ask him to stop, I thought. Tell him it hurts. Tell him no. Tell him now.

“Oh, God, Esther,” I heard him groan. “I’ve never done this with anyone. You are my first. The first one I’ve ever done this with. My cock is in your beautiful ass.”

Other girls bitched about their first time, how much it hurt when the boy fumbled around and jammed his cock in them, but he had made mine doubly special. My first time hadn’t hurt at all, thanks to him. I could give him this. For him, I could take this pain. I would be his first in something. Dammit, I would give him something he hadn’t had before, no matter how much it hurt.

But, I realized as I bit the pillow and clawed at the blankets beneath me that it didn’t hurt anymore. He wasn’t moving, but he was still in there. And it didn’t hurt. His cock was in my ass, and it didn’t hurt.

Then those damned magic fingers were back. I could feel one of his hands working his spell between my legs as his other caressed my breast. His hips hunched forward and I felt him slip another millimeter inside me. I gasped. Not with pain. With an odd… pleasure. It felt good. Strange. But, good. Strangely good.

I have since read that there are more nerves in the sphincter than there are in the vagina. But, they weren’t telling me anything new. Just explaining what I experienced when I realized I could feel him in a way I couldn’t when he was fucking my cunt.

“More,” I moaned.

“What?” He asked.

“Give me more,” I groaned, trying to push back into him.

“We should take this slow and easy.” He panted. “I don’t want to hurt you.”

“I’ll… ungh… tell you if it hurts.” I grunted. “Slip some more of your cock in.”