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.
