My Bottom and Me

A few months later, my road of self-discovery had a highlight when I went to a convention in my old home city. I contacted my ex-roommate Judy and told her of my upcoming visit. She was happy to hear from me and was very insistent that I plan on staying over the following weekend with her. Admittedly, the idea was at the back of my mind before I called and it didn't take a lot of convincing on her part to get me to agree. Part of me was happy to spend time with a former lover. Part of me also knew that it was going to be my first opportunity to try out my new skills with someone I cared for and trusted. I suppose I was also seeking someone that I could share this new found part of my sexuality with. I don't really mean just in bed. I guess that I also felt the need for a friend I could talk to about it who I knew would be accepting and supportive.

Judy insisted that I pack something appropriate to wear out and that we would hit the town. I knew that probably meant a nightclub and possibly one of the local lesbian clubs that she occasionally frequented. I added a "LBD" and a few of my more casual items from my wardrobe for the trip. Of course, my anal kit was now an established part of my travel items and I had even added some things that were left permanently packed.

The weekend spent with Judy, and the emotional build-up before, was wonderful. She was initially pleasantly surprised and shocked over the changes that had occurred in me since we were last together. We spent a good part of the weekend in bed playing. Much of that play was focused on providing pleasure to each other's assholes.

I won't go into a lot of the details of that weekend other than to mention a few of my more notable experiences. The first was that giving each other enemas was a rather unique and intimate experience and one that I have since come to enjoy more with other lovers. We spent a lot of time kissing and just holding each other while our bottoms filled and I thoroughly loved it. The second was that I found I loved having her tongue rimming my ass. She had tried this before, but I guess my mental reservations kept me from being open to the experience. My orgasm with her tongue in my ass and fingers on my clit was one for the record books. Third, our excursion to a lesbian club with both our asses plugged was so very hot. I can't remember a time when I got so horny from just dancing and making out with someone. The plug was a constant reminder of what was to come later after we got back to her apartment and my pussy was literally drooling the entire time. Last, but not least, my ass was fucked for the first time by someone else. The trip to the club was followed by her removing my plug and replacing it with a strap on dildo. While not as big as the dildo I used for that purpose, it was more than enough to do a good job. I found I loved the feel of her hips slamming into my ass cheeks, the feeling of her hands holding my hips and I even liked the way she later spanked my ass in time with her thrusts. My orgasm was no less intense, and perhaps more so, than those produced by my solo experiences. It was certainly nice to have someone to snuggle with after my orgasm exploded in my body.

As I mentioned earlier, I was in need of someone to talk to about my anal discoveries and there was no one better than Judy. She was largely responsible for my journey of discovery and served as a good metric for my progress. She turned out to be more than just a sympathetic, understanding listener. She turned into a good mentor as well. She was free with her suggestions and personal recommendations for further experimentation. What few areas that I lacked in the area of confidence were quickly resolved by our pillow talk discussions. Of course, the fact that these discussions were spread out between some very satisfying romps, didn't hurt at all. She even made some suggestions about how to go about "training" a man to make love to my ass. This topic was something that was starting to pop up on my radar screen on a more frequent basis. I think my weekend with Judy made me finally recognize the fact that I was over my past trauma and ready to move on and explore with a male lover.

My farewell with Judy was sad, joyous, and overlaid with more than a little residual horniness. We shared kisses and tears as we said our goodbyes. That weekend spent with her was one that I can clearly point out as a turning point in my sexual history. Sometimes the word epiphany comes to mind.

I returned to my hum drum, largely non-social life of work and masturbation. I was starting to make a few friends, but none that I could share the intimate details of my life, at least not like I could with Judy.

On one business trip to San Francisco I stopped into a really cool store that was largely devoted to toys. It became an instant favorite for a couple of reasons. First, it was owned and ran by women. Second, as I found out later, most of the employees were also partial owners through an employee ownership plan. Third, they only sold items that passed the employees "road test." Lastly, they were very open about discussing the pros and cons of the items they sold. It was the first time that I can really say that anyone actually gave me anything approaching customer service at that kind of store.

I wound up buying my first strap on harness and two dildos to go with it. One of the dildos was medium sized and similar to the one that Judy had used on me. The second was larger intended more for vaginal use than anal. I didn't have a lover in mind to use these with, but I thought a selection was important for any future lovers. As a matter of fact, I have no idea why I even bought them other than the hope that I may have someone to share them with in the future. It was becoming increasingly clear to me that I was in desperate need of someone to share my bed.

That eventually did happen a few weeks later. I met Cathy when a co-worker almost forced me to go with her and her girlfriend to a lesbian club one weekend. The co-worker was openly gay and she seemed to immediately recognize a similar attraction to the fairer sex in me.

Anyway, Cathy and I became an item, at least to a limited extent. Cathy is married and she and her husband have an agreement that allows her to go out occasionally in search of feminine company that her sexuality required. That was what she was doing at the club that night; that is, searching for a wife for the night. What can I say? I was a little drunk, feeling care free, and above all, very horny and needy. Our relationship evolved into something that would best be described as "fuck buddies." We both knew it was temporary and had no future, but we both were satisfied with the short term benefits of our relationship. She was devoted to her husband and family, but at the same time she had needs that were not satisfied by home and hearth. She is a wonderful, experienced lover, but unfortunately did not share my new found love of incorporating anal eroticism into the bedroom. It wasn't that my ass was totally ignored, nor hers for that matter, but it never was more than a occasional part of our sex together. It remained no more than an occasional diversion that she happily engaged in, although largely just to please me.

Cathy and I are still good friends to this day, and occasional lovers. Her place is permanently marked in my memory because she filled a void in my life and because I was with her when I met Gary. I won't go into the details about how I met Gary at this time. That is another story in and of itself that I hope to share with you one day.

After we met, Gary and I became lovers on our third date. I was itchy and horny by that point but forced myself to take it slow. From the beginning, I saw more in him than a potential fuck buddy and I was determined to build the basis of a relationship before taking him into my bed. My discipline surprised me. I was sexually attracted to him from the beginning and that attraction continued to simmer and build through our first two dates.

He turned out to be a wonderful lover, I am happy to say. He was everything I had dreamed of in a lover, tough and forceful when I needed him to be, and sensitive and gentle when I needed that too. I thought of him as my "lesbian trapped in a man's body." He entered my life at a point when I had mostly given up on the concept of a "Mr. Right." At that point in my life I would have simply been happy with a "Mr. Right Now."

It amazed me how he could somehow sense my needs, even when I hadn't even given voice to them. It was like he had a sixth sense. That is not to say that I was totally silent on the subject of my needs. I almost immediately developed the kind of trust and intimacy with him that allowed me to open up and share all my dreams, fantasies, kinks, and sexual needs. That included my sexual history. When it came up, I shared my failed early experiences with anal and even some of my successful recent experiences. I told him that I was open to exploring that with him, but I was waiting for the right time. He accepted that and I never felt that I was pressured by him in any way. When it happened, it would be when I was ready and on my terms. That was a huge relief for me.

I eventually shared a few details of my bisexuality with him. As with anal sex, he was accepting and never pushy about that. That was an even bigger relief to me. My status as a bisexual woman had been a deal breaker with more than a few men in my past. It seemed that most men were either threatened by it, or saw as it an opportunity for me to serve the role of providing them their porn inspired threesome fantasies. The few times that I gave in to this desire to live out their fantasies, I found that they often featured themselves in the role as both the male porno stud and director. These experiences were mostly frustrating when the guy turned out to be neither mentally or physically capable of living up to the details of his fantasy, much less mine.

Gary, on the other hand, seemed relaxed and comfortable with my proclamations about my sexuality. He was a widower; his wife had been killed in a traffic accident a few years before. She was bi as well and he, like Cathy's husband, had seemed to work out his issues with it and learned to accept it as just part of her sexuality that he was not able to satisfy, at least directly. I had always envied Cathy's relationship as some sort of ideal and finding Gary seemed to help me find my own ideal.

I had been dating Gary for a little over a month when we went out to dinner to celebrate his birthday. While sitting in the restaurant I leaned over and whispered to him, "I have a special present for you later." He saw the playful gleam in my eye and knew something was up.

"Yea, what's that?" he asked.

"It's something no man has ever had before," I replied, smiling at him.

"Care to elaborate," he asked. I am sure he knew where this was going but he was more than willing to continue playing my game. I was sure that he was just enjoying having me put words to it.

"Well, I was trying to come up with a very special birthday present for you and I thought that my anal cherry would qualify as being special," I whispered.

"Yea..." he stumbled for a moment, "I suppose that would definitely qualify as being special."

"As a matter of fact, its all ready for you right now." I continued.

"How's that?" he inquired.

"Well, I made sure it was all clean and lubed for you, and right now I'm sitting here with an anal plug in my tight little asshole so that its ready to be filled my your big ole cock. By the way, I'm not wearing any panties either and I have to squeeze the plug real tight to hold it in so that I don't embarrass myself here in the middle of the restaurant."

My hand that was resting on his thigh felt his cock lurch in his slacks in response to the bombshell that I had just delivered. It was clear that I had his attention and the teasing nature of my words got his cock's attention as well. Needless to say, we didn't stay for dessert, at least not at the restaurant. Dessert was waiting for us in my bedroom after we got home.

Hmmm, what can I say about the first time I experienced Gary's cock in my ass: hot, intimate, lusty, passionate, and above all, loving. As it turned out, he had far more patience then I did. I was in heat and ready to feel him driving into my asshole. I think that fact amused him. He took advantage of it and used it to tease me, first with his mouth and tongue, and later with his cock driving into my pussy. During this time, he teased my ass by gently nudging the plug that was still in me, keeping my needy ass ready for him.

I had always loved his very thick, slightly above average length cock in my pussy. It filled me and satisfied me in ways that I could have never imagined. His patience, staying power and endurance were better than any previous male lover's. I loved the way that he always made sure I came, usually several times, before he filled my pussy with his seed. With all that said, vaginal intercourse that night was just a warm up, just foreplay. Nevertheless, he did bring me to a great orgasm as he fucked my pussy.

As I recovered from my orgasm, I saw him reaching for the lube that I had left strategically placed on my nightstand. I felt a rush of excitement flow through my body as I realized now was the time. I flipped over into a doggy position as he lubed his cock. I felt him tugging on the plug and gasped as it slid out, leaving me with that empty feeling that I knew was going to be short lived this time. The feeling of the plug was replaced by that of his thick finger as he lubed up the wrinkled opening to my ass. I concentrated on relaxing and getting into that calm place that I had practiced so many times before. His finger entered me and spread additional lube inside. I unconsciously grunted when a second slippery finger joined the first in my tunnel.

"You OK?" he asked, a little concerned.

"Yea, feels good, go on," I replied, trying to reassure him. He continued lubing me, refreshing the lube that had previously been applied on the plug.

I felt his fingers withdraw and were quickly replaced by the head of his cock against my anus. Gary has a large head on his cock that I loved in my pussy but I knew that it would be a little difficult to accept in my ass. It was not like the cone shaped plug that tapered gradually, the first part of his cock to enter me would be the widest.

I had thought that Gary would push into me quickly and had at least mentally resigned myself to this fact. What he did next surprised me, and made me appreciate him as a lover even more.

"I'm going to hold still, just push back onto me as fast as you are comfortable with," he said.

And that is exactly what I did. I won't say that there wasn't some pain. Maybe pain is not accurate. Let's just say there was some discomfort, but when I felt the full girth of his cock head push into my ass and my sphincter sealed around his shaft, I felt a mixture of emotions and feelings: accomplishment, pride, relief, love, and yes, more than just a little pleasure.

I took a moment to catch my breath and then I continued on, pushing his cock deeper and deeper into my ass. This was something I was familiar with and confident I could handle. It was little different than inserting the plug or dildo with a few noticeable exceptions. The first being that after I got the plug fully inserted, I was able to close around the neck and my sphincter was not fully stretched. The second, was that Gary was thicker than the dildo and kept my ass stretched more than I had ever experienced. The third was this was warm, throbbing male flesh of a man I cared deeply for and not the cold, unfeeling latex of a plug or dildo to which I had become accustomed.

The feeling of his mushroom shaped cock head spreading me as I worked him in deeper was also something new. With that said, I wouldn't say that it was unpleasant, just different. Another thing that I had not considered was that his cock was warm, even warmer than my latex or silicone toys that I pre-heated in warm water. I also thought I could feel his pulse beating in his cock.

I was sort of lost in this myriad of sensations and was surprised when I felt my ass checks come to rest against his hips. I wiggled my ass around a little to make sure I had it all and another fraction of an inch slipped in. I just let him soak in my ass for a moment and absorbed all the different sensations coming from my bottom.

"Are you OK," Gary asked, the love and concern evident in his voice.

"Mmmm, yea, lovely... feels good... just give me a minute," I groaned.

"Take all the time you need, I'm not going anywhere," he chuckled.

"Good, I'm glad," I responded and experimentally clasped my muscles around my lover's cock.

"Oh yeah, that felt good," he exclaimed.

"Yea, I liked it too," I responded.

I started moving back and forth slowly, fucking his cock in small increments that increased as my confidence and comfort level grew. I felt his hands on my back and ass caressing me as I tried him on for size.

Encouraged and emboldened by my body's response, I asked my lover to join in on the activities, "Fuck me Gary, slowly at first, fuck my ass, please..." I pled, the lust almost dripping from my words. .

Gary responded by gently grasping my hips. His cock slid an inch from my ass and slowly returned to its resting place deep in me before stopping for a moment. He continued to repeat this, over and over, the length of his strokes gradually increasing. I lowered my head onto my arms and just allowed him to take over control.

That was something that surprised me, that is, the control aspect of him fucking my ass. Sex with Gary had always been more of a give and take proposition. That was not what I felt at that moment though. I had given up control to him to fuck me, to use my ass, and in so doing, I was receiving pleasure in return. The quicker and deeper his thrusts became, the more this feeling grew in me.

Gary was taking his time, slowly increasing the intensity of the fucking that he was delivering to my ass. I recognized that he was being his gentle, sensitive self and making sure that he was giving me time to adjust. I was more than comfortable now and ready for more and decided that I needed to tell him so. My mind and body was ready for than just gentle lovemaking. I needed to be fucked and fucked hard and fast.

"Gary, baby?"

"Yes sweetie?" he replied.

"I need you to fuck me now, I'm ready. Take me... use me... give me your best," I gasped. "I'm not a china doll. I'll let you know if it's to much, OK? I promise," I said, my lust almost dripping from my words.

It wasn't as if Gary immediately began to plunder my ass with the bludgeon of his cock, but the rate of the increased tempo certainly picked up its pace. My cries of pleasure were soon echoing in my bedroom and my hips involuntarily snapped back to meet his thrusts, crushing my ass cheeks against his hips and flinging his low hanging balls against my splayed pussy lips. My ass was completely open and accepting his cock, allowing its slippery length to slide freely into my hot depths. I decided that maybe I was a little too open and starting to contract my ass around his cock as it slid inwards. He seemed to appreciate this additional stimulus as much as I did. His grunts were soon mixing with my own cries of joy.

"Oh yes... fuck me... fuck my ass with your cock..." I unthinkingly cried out in passion. Gary responded by increasing the pace, power and the urgency of his thrusts.

My level of arousal had increased to the point that I knew, from my solo experiences, that I needed more. I slid my hand down to my clit and began to work it over. I started first with a gentle caress but that soon escalated to more urgent rubbing and pinches. The rough treatment of my clit seemed to blend perfectly with the odd pain/pleasure emanating from my ass.