A Promise Kept, with Regret

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The end of a beautiful relationship.
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This story is a continuation of Shattered Hero by fellow literotica author and friend dkalish. You will want to read that story before this one. This series of events in her life are obviously difficult for her. They are recounted here with her approval.

*****

I had uprooted my life on a whim, or so it seemed. After meeting Brandon on vacation, I moved from New York to Chicago, switched offices in my law firm, and moved in with him immediately. Within two weeks of our first meeting, we were building a new life together in the windy city. Impulsive, I know, but there was no doubt in my mind that it was the right thing at the time. Yet, it all fell apart because of sex - my past, his past, and our inability to get past the past.

Anal

Only days after leaving him on Antigua, I rang the bell at Brandon's apartment in Chicago. I was greeted with open arms, a near suffocating embrace, and a deep kiss that tickled my insides and let me know how much he missed me. It was just the welcome I had hoped for. Within minutes, we were naked, in bed, with his cock deep inside me. Although I intended to spend the rest of my life with this hero and we now had all the time in the world, we both climaxed quickly. Only afterwards did I get a tour of our new home, which was conducted in the nude while we clutched at each other's bits.

Chicago was, well, interesting. As a Southern California beach bunny, moving to New York was a thrill - the intensity of life in a real city was a jolt to my suburban upbringing. Chicago was less frenetic, colder, but still a vibrant community. As a young Associate lawyer working in a national firm, I still put in insane hours. The managing partner in the Chicago office was, you might say, an asshole. "Billable hours" were all that counted, and boy did he count. Brandon also worked hard, and continued to travel to exotic locations for the real estate development firm. But with our combined salaries, and his military disability benefits, we lived well, enjoying great food and the cultural life of the city I now called "home."

The sex was great. No matter how late I got home from the office, I made sure Brandon had his daily orgasm. Sometimes if it was too late, I'd simply crawl into bed, take him into my mouth, suck him dry, and swallow my "nightcap." Most of the time, though, he waited up for me, we unwound from our busy days, and then spent an hour or more making love before going to sleep. A tentative and scared veteran when I met him, Brandon quickly grew into an accomplished and skilled lover.

When we were in Antigua, I had promised him my ass when we had sufficient lube. In retrospect, I guess I brought up the possibility, not him. Anal was never my favorite, but in that first day of marathon sex I had assumed he would want to take me in that hole as well - after all, he's cum just about every other way possible. In Chicago, we made love in nearly every position and he enjoyed cumming in all my orifices - except that one. Over the months, though, Brandon started dropping hints, and I knew I had to honor my promise. I was eager to do so - for him.

I planned the event carefully. Brandon was traveling, again, and due home late Friday. That morning, I cleaned myself out, lubed myself up, and inserted the small butt plug I had discretely purchased over the internet. All day at work I was pleasantly distracted. Sitting in meetings, or even alone in my office, I kept shifting around in my chair, very aware of the plug in that most unusual of places. After work, I gave myself another enema. When Brandon got back to the apartment around 10 PM, I jumped him at the door, fucked him silly, and relieved some of the anticipation that had been building inside me all day. That Saturday, we had a lot of errands to do, but I told him that I had a special evening planned. Before we set out, I took my third enema and inserted the butt plug again. While doing errands, I was perhaps even more aware of what was in my ass - and what would be there later that day. While we were in the grocery store, I pulled Brandon into the "family" bathroom, got on my knees, and blew him then and there. With a full load in my mouth, I looked him in the eyes and slowly swallowed the lot. I was supercharged - but I also wanted to take the edge off him. If we were going to do my ass, I wanted him to last.

That evening, we had a light supper, and then I asked him to clean up while I took care of some things. I still had not told him what would be his special treat. After another enema to ensure I was fully clean, I put on the lingerie I had purchased on Antiqua, which still had special memories for us, did my hair and makeup, lubed myself well, and slipped into bed. I then asked Brandon to freshen up and join me. As he pulled back the covers, his eyes widened and a smile crossed his face. He still did not know what was coming, but seeing me in my flesh colored pushup bra, thong, garter, and silk stockings certainly had the desired effect. He took his prosthesis off his shattered leg, wheeled into bed, and took me into his arms.

While kissing and holding each other, I whispered to him, "I made a promise a long time ago. Tonight, I want to honor that pledge. I want to you to take me in the ass." His face brightened, and his already engorged cock seemed to grow even harder in my hand. Minutes later, after sucking him and lubricating him further, I lubed him up as well, dispensed with my thong, and opened myself to him. Kissing and holding me, Brandon directed himself to my backdoor and pushed slowly to enter. Since I was properly stretched and lubed, his head slipped in easily. Encountering just a touch of resistance as he pressed against my sphincter, he was soon balls deep in me. I must say that, for the first time, anal felt wonderful. The preparation was worth it. I was full and his cock was squeezed tight. Slowly, slowly, we made love. My vagina was oozing fluid, which Brandon generously smeared around my clit with his fingers, rubbing my sensitive little nub with every stroke in my rear. The anticipation that had built over the last days and the sensations quickly drove me over the edge in to a nicely satisfying orgasm. After recovering slightly, I pushed him off me, rolled onto my hands and knees, and demanded that he fuck my ass doggie style, his favorite position for vaginal sex and, I hoped, for anal sex as well. His free hands now grabbed my breasts and rubbed my pussy continuously. It was amazing.

I'm usually vocal during sex, but now I let loose a flood of obscenities, screaming for him to fuck my ass with his fucking penis, cock, dick, rod, whatever. I told him I was his whore and he should use me anyway he wanted. Brandon in turn pounded my ass. Abandoning any restraint, he plunged in and out, his hips slapping into my trembling butt cheeks as his cock penetrated deeper and deeper into my forbidden hole. He continued to rub my clit. Laying my head on the mattress, my own hand joined his. While I frigged my pussy, I felt him grow huge and, impossible though it seemed, harder. My steady stream of highly obscene encouragement was working, I guess. Then, as my ass gripped him tightly, his cum shot through his shaft and exploded into me. I was right behind him, following only seconds later with a mind-blowing orgasm that ripped through my body. We both collapsed on the bed, breathing heavily. Eventually, I rose and cleaned up a bit, as did he, and we returned to bed knowing that we had shared something special that night.

Threesome

In retrospect, our anal escapade was a turning point in our relationship, but not in a good way. Perhaps it was the forbidden fruit. Perhaps it was my over-the-top performance, the letting go of my inhibitions, the string of obscenities. Whatever the cause, I noticed a subtle change over the next weeks. Brandon began inquiring about my past sexual partners. We had shared some of our histories with each other, but not the details. Now, he wanted to know more - and seemed fixated on my "number." I knew mine was larger than his, but it also depends on how you count. In my mind, my spring fling really counted as one because it was one continuous fuck session, though Brandon insisted that it was three different guys and each should count. The same for my yachting experience with Paul and Sam. What about Janice and John on Antiqua the day before I seduced Brandon? And does making love with women really count the same as men? Including guys early in college, before Prof. Smith, my number depending on the rules for counting could either be 9 or 16. See, counting can be hard! Brandon's was three, regardless of the arithmetic.

The difference in our numbers seemed to gnaw at him. Whenever we'd disagree, this seemed to come up. We were thinking of getting a new mattress - or at least I was, since I regarded his existing bed as too lumpy. "Well, you've slept on enough of them," he'd say, making clear through his tone that he meant much more than his words alone implied. Once when he traveled, I teased him about not allowing any girls in the hotel restaurant to pick him up, as I once had. "Well, only someone like you would do that," he snapped back with a measure of hostility in his voice. As much as I tried to assure him that I loved him and only him, he seemed to be increasingly bothered by my past and what he obviously considered an inappropriate number. I wrote this all off to his injury and the lack of self-confidence it had induced. I knew he felt less than whole, worried that he was damaged goods, and so on. I was determined to build his confidence, let him know I loved him, and that he was a great lover.

One day, after yet another subtle dig at my history, I suggested that if it bothered him, "he was free to experiment with other women - or men - as the case may be." I don't think he appreciated my offer of other men. But, I continued with a soft purr, "I'd like to join you, if possible." He raised his eyebrows and grinned, but did not respond. I let the suggestion slide. But this too seemed to creep into conversations and, especially, disagreements.

One day, Brandon did cuddle up to me, put his arms around me, and whispered "Maybe we should try a threesome." He was especially passionate that afternoon as we made love. He made a similar suggestion the following week, so I came to believe he was serious. If he wanted to sleep with another woman to equalize the count, so be it. If he wanted me to join them, that would be OK too. I loved him and wanted to make him happy, even if this meant sharing him with another woman. As his increasingly frequent hints became more direct, I began to hatch a plan.

I had kept in touch with Adrienne over the years. While I had moved on to Law School, New York, and now Chicago, she still worked as an assistant at the same law firm in Los Angeles. Though we did not see each other often, I still had very fond memories of our times together, especially the first time we had driven to the wild side and made love in Santa Barbara. We spoke regularly on the phone or via Skype and kept few secrets from one another. She was not in a relationship at the moment, and now swung both ways - as the expression goes. I unloaded my problems on her, especially the growing tension with Brandon over our sexual histories. Probing around the edges, I inquired whether she might like to come for a visit, though I was really asking so much more. The next week, she called back and said that she would be "delighted to spend time with both of us." We both knew what that implied.

The following weekend, Adrienne arrived at our doorstep. I had only told Brandon that she would be visiting, not anything about my plan. Adrienne was a cute as ever. That evening, we ate at one of our favorite Italian restaurants - the only proper meal we'd get the entire weekend as it turned out! With a couple of bottles of Chianti in us, we were warm and fuzzy, laughing at each other's jokes, filling Brandon in on our times together in LA, and generally having a good time. It was like Adrienne and I had never parted. Two halves in my life appeared as if they would make a whole.

Once back at the apartment, we all fell on the couch laughing yet again at some silly joke. I leaned into Brandon on one side, Adrienne did the same on the other, and the sparks flew - stopping all of us in our tracks. I reached up and kissed Brandon, sliding my hand up his thigh at the same time. Adrienne did the same. Brandon put his arms around both of us, taking turns kissing us. Eventually, though, he concentrated his attentions on Adrienne. I unbuttoned his shirt, sliding my hand across his sensitive nipples. I then unbuckled his pants and, while he was still kissing Adrienne, pulled them down to reveal his rising erection. Putting my hand on him, I intruded on their kiss, locking lips first with Brandon and then switching to his apparent surprise to Adrienne. Her hand joined me on his now throbbing cock. After we broke our kiss, both Adrienne and I moved to lick Brandon's hard dick, running our lips up and down the opposite sides of his erection, alternating taking him into our mouths, and occasionally kissing each other when our lips ended up in the same proximity. After a few minutes, I suggested that we move the party to our bedroom, to which both Brandon and Adrienne eagerly agreed.

By unspoken assent, Adrienne and I now concentrated on Brandon, laying him between us and caressing and kissing him from head to groin. Knowing how sensitive he is about his wound, I made sure I was on the side of his missing lower leg. Orchestrating our positions, I maneuvered Adrienne onto her hands and knees and - knowing how much he liked "doggie style" - guided Brandon into her from behind. Both closed their eyes with a contented sigh as Brandon fully entered her. Adrienne then grabbed me and swung me around in front of her, bending down to lick my pussy. Brandon's eyes opened wide as he witnessed our friend lapping up my now copious juices and sucking on my clit. He forcefully fucked her from behind, pushing her face further and further into my cunt with each stroke. As we all rose toward orgasm, I wanted to prolong the moment and slid out of Adrienne's reach. I pushed her onto her back, took Brandon's cock and deep throated him, and then guided him into Adrienne once again, this time in missionary style. I lay next to them, watching my boyfriend fuck one of my closest friends. Not wanting to be left out of the action too long, however, I began to suck on Adrienne's puffy nipples - now hard, rubbery nubs. I moved around behind Brandon, kissing my way down his back to his ass, where my tongue took a quick swipe across his hole, eliciting a deep groan as he continued to plow into Adrienne. I reached between them to rub Adrienne's clit while kissing first Brandon and then her. It was electric.

As Brandon was getting close, I interrupted the action again to change positions. This time, I moved Brandon onto his back, maneuvered Adrienne onto his cock cowgirl style, and then seated myself over Brandon's mouth facing my friend. While Adrienne rode his dick and Brandon's tongue worked magic on my clit, we girls locked ourselves in a deep kiss while fondling each other's tits. Adrienne went first, crying out as her orgasm wracked her small frame, falling into me. As her pussy spasmed, Brandon followed, erupting inside her as he trembled beneath me. Overwhelmed by their pleasure, and Brandon's skilled tongue, I climaxed soon after. As we all collapsed, I rolled over to Adrienne and licked the cum oozing out of her. She held onto Brandon tightly as her sensitive clit enjoyed another round. Exhausted by the long day, we soon fell asleep, Brandon in the middle, Adrienne on one side, me on the other.

The next morning, I woke to find Adrienne's head between my legs. I pushed her away, desperate to pee. I freshened up a bit and returned to bed, where Adrienne and I slipped into a luxurious 69. What a wonderful way to begin the day. As we rose, apparently making just a bit more noise than we had hoped, Brandon woke as well. As he stroked his morning wood, he watched us tumble over into bliss. Grabbing Adrienne as soon as she came, Brandon proceeded to pound her to orgasm again. Still hard, he pulled out and squirted his seed over her small and puffy nipples. I eagerly lapped up his contribution, and then shared it with Adrienne in a long and passionate kiss.

We managed some breakfast, but soon found ourselves caressing and stroking each other's sensitive parts while at the table. We spent most of the day fucking wildly. Eventually, I became aware of the fact that Brandon had not entered me the entire weekend, which seemed odd. Though I did not suffer any lack of orgasms, all administered at the loving hand or mouth of my beautiful friend, Brandon only fucked Adrienne. She even gave him her ass later that day, but only after I had licked her well and used my tongue to spread her little opening. All in all, though, it was a very sensuous and uninhibited weekend. We were sad to part on Sunday afternoon.

Gangbang

I had hoped that our weekend with Adrienne would alleviate some of Brandon's angst about my past. I was wrong. I figured we had evened the score a bit, and he should appreciate that. By his reckoning, we had each elevated our count by one. I argued that since I'd been with Adrienne years before I ever met him, she shoudn't count against my number. Brandon argued that since it had happened in the context of a threesome, it was different and should count. I tried to laugh it off and claimed it wasn't a competition. He continued to stew about it. Sleeping with Adrienne appeared to have been a mistake, despite my best intentions.

Soon Brandon began hinting about wanting to watch me fuck other guys. "I love you, and only you," I responded. "I don't want that - and I don't think you do either."

I urged him to drop the idea. But he persisted, about once a week or so making some comment that let me know the thought was still rumbling around in his mind. I did not know if this was a test of some sort - did I really love him? Would I really fuck other guys? Or if this was some fantasy of his that he really wanted fulfilled? I explained over and over that I was not interested, that the weekend with Adrienne had actually harmed our relationship, and that any coupling with additional guys would surely turn out to be a disaster. Still, he would not let the subject drop.

"Fine," I finally said one day when he had raised the idea yet again. "If this is something you really want, I'll do it. But remember, this is what you want, not me." He seemed happy. I sort of hoped this would be the end of it.

A few days later, however, he casually mentioned over a late dinner that he had arranged for a couple of guys to come over on Thursday. I cocked an eyebrow. "Really," I asked? "You sure you want to do this?" He nodded. "A couple," I asked again? "That wasn't the deal."

"I've always said plural," he responded with a slight edge in his voice.

"No," I said angrily. "I love you. I want to make you happy, if this is what you are sure you want. But 'guys' is too much. I won't do it."

"It's already arranged," he said in an ice-cold tone. "You will." I walked out of the room and cried myself to sleep.

We did not talk much over the next few days. I worked late, avoiding him, I think. We did not touch one another, foregoing our nightly lovemaking. I was miserable. Yet, I was also increasingly resigned to the idea. If this was so important to him to risk our relationship, maybe I could do it for him?

On Thursday morning, I woke to find Brandon already gone to work. A note on the kitchen counter read "Wear your Antigua lingerie today. Be home at 8 PM." Boy, he was really rubbing it in. My favorite underthings, firmly associated with one of the best memories of my life, and he wanted me to wear it today? Today? For other guys? Dutiful girlfriend that I was, I pulled out these special undergarments and dressed for work.

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