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Observer By Enigma "Ohhhh!" Jeannie's moans of pleasure echoed around the room. Her breath cut off as her body first went rigid, and then shook as waves of pleasure washed over her. "I'm... come... ming...!" I gasped as I drove deeply into my wife and felt the pulses of climax shake my very being. I collapsed on top of Jeannie, and felt her wonderful C-cup breasts mash against my budding A-cups. I rolled to the side, pulling her with me, maintaining the intimate contact between our boobs, staying buried deep within her. As we both struggled to regulate our breathing and racing pulses, I reflected on how we got here. Jeannie and I met and fell in love in college, while I pursued a degree in communications, and she was working toward an advanced degree in psychology. It was the beginning of the last year of school for each of us, even though she was in her seventh year of college, while I was in my fourth. Our romance blossomed into flame very quickly, and led to an intense sexual relationship soon after. It wasn't long before she discovered my secret addiction, cross-dressing. I think that may be what influenced her to shift her specialty to the treatment of gender identity disorders, as she sought to understand what made me tick. Jeannie was gorgeous. About 5' 6", and around 120 lbs. with a trim, well toned body measuring in at 34C-24-32. She has beautiful auburn hair that I know is natural based on the color of another patch of her hair that I am intimately familiar with. I am about 2 inches taller, but rather slender. Her bras fit me just fine, excepting the filling for the cups. Given my penchant for dressing, I measured myself at 34- 29-30, and tipped the scales at a hefty 125. Not exactly a womanly figure, but it served as a reasonable canvas for painting the picture of femininity I seem compelled to present on occasion. My longish golden blonde hair helped too. Soon after graduation, we were married. Jeannie joined several other psychologists in a thriving practice, and I found work at a local advertising agency, doing rather obscure work for the various clients of the firm. That suited me fine, as I did not have great self- confidence, so I was able to do work that I'd trained for without the public interaction that frequently went with my career. I think Jeannie was using me to hone her skills in the counseling of GID patients. I had always felt that I was simply interested in an occasional bout of dressing in women's clothes. And that was all it was over the first two years of marriage. During that time, Jeannie first tolerated, and then came to support my 'hobby'. As she came to accept it, she gradually began to participate in my efforts, and even encourage it in some ways. By our second anniversary, my skill had progressed with her help to the point that I semi-regularly went out en femme with Jeannie for shopping, a movie, or dinner. I was comfortable in public and felt I made a reasonably attractive woman. Although I didn't recognize it at the time, I think this was about the point that her focus shifted subtly from my interest, which was cross- dressing, to her interest in transsexuals. As I say, it was not an obvious shift, but very gradual, and I did not pick up on it for some time. Maybe six months later, thanks to her guidance, my thinking had also followed that subtle shift, really without a conscious awareness on my part. I am sure the change was at least in part a result of 'unofficial therapy' administered by my wife. We had always been good at communicating with each other, and talked at length about many subjects, including gender identity issues and how they applied to me. So it was maybe seven or eight months ago that I made the decision to begin transition as a M2F transsexual. At least, I think I made the decision. What that amounted to was to begin taking hormones, and extend my now fairly frequent cross-dressing to be full time. In other words, I began my Real Life Test. Based on letters from my therapist (Jeannie), and thanks to the obscurity of my work at my agency, I was able to continue in my job while dressed as a woman with minimal impact. And Jeannie made sure the hormone regimen was such that it would have no impact on our still sizzling sex life for a long time, while gradually helping my body shift to a more feminine contour. My female impersonation has progressed to the point that I feel I am quite attractive, and apparently so do several of the men at the office, who ask me out with some regularity. Our breathing had settled more or less to normal as I was lost in reverie. I was snapped back to the present by Jeannie's words, "A penny for your thoughts." I blushed and averted my eyes. "Still have concerns about this journey you're on?" she asked. "No... Yeah... I don't know!" I fumbled for words. "Actually, that was not what I was thinking about. Not directly anyway." I blushed again. "I was just wondering what it's like for a woman. The sex, that is." Jeannie grinned. "Well, you get the chance to observe often enough!" She giggled. I snickered too, at the reference to our frequent encounters between the sheets, but sobered quickly. "Actually, I am always too distracted to be much of an observer." Jeannie looked pensive for a few moments, while I searched for something to follow that up with. I'm not sure who was most shocked at the words that tumbled from my mouth next, "Maybe I could watch you make love to someone else." When what I said sank in fully, I gasped in dismay. When Jeannie recovered enough to speak she said incredulously "Patrick! Um, Patricia! Are you suggesting I violate our wedding vow?" "No! Not really." But the thought had wormed its way deep into my brain and wouldn't dislodge. "It's just that I love the sex I have with you, and I don't really know what I would be getting into if I complete transition!" "Well you can forget that idea right now!" "I'm sorry! I don't know where that thought came from." But Jeannie had already turned her back to me, and was conspicuously ignoring my words. For the next several days, the atmosphere was decidedly chilly in our bedroom. For that matter, it was quite cool in any room we both occupied at the same time. No matter how I tried to apologize, she wouldn't listen. Finally, after almost two weeks, she snuggled up against my back one night after I had settled down and was almost asleep. Her arms came around me and stroked some fascinating spots as she whispered, "I'm sorry I've been such a bitch this past few weeks." What quickly followed was a frantic coupling that was frenzied due to the incredible length of the abstinence. At least in our married life, it was a record drought. When we came down from the rush, I spoke softly, "I'm sorry. It was an awful idea. It's just that I have this fear that I am giving up something incredible with no assurance that there is anything to make up for it!" "Shh. I know. If you could just feel what I feel right now, or even see the depth of my feelings as I climax, you wouldn't worry. The female orgasm is fantastic! From what I've observed, it is much better than your male one." "But how do I know that? My focus is so tied up in my genitals that I never truly see your release." She thought for a while. "Maybe you're right. You really have no way of knowing. And also maybe it is correct that observing without participation would give you the chance to really absorb what I feel. But I made a vow..." I sighed. "I know. I'm sorry. I've tried to tell you it was a bad idea. Forgive me?" She continued to frown with concentration. Almost to herself she said, "Maybe there's a way... Maybe that wouldn't be breaking the spirit of the vow." "Hunh? What are you talking about?" She spoke up a little, more like she was talking to me than herself now, "If we made a pact between us, to sort of clarify our definition of our wedding vow..." She could see I was lost. "What I was thinking was that if I swore to never engage in sex with another person unless you were there, and you initiated the contact, then it would prove that you knew of and approved the act. And you could swear the same thing. Then we both would have absolute confidence in the fidelity of the other, and not be breaking our marriage vow." I thought for a moment. "I don't know. I'm not sure I really want you... Um, what do you mean by me initiating the contact?" I was pretty flustered by this turn of events. She considered her words. "Well, before I could have sex with another man, you would have to, for example, guide his cock into my pussy with your own hand." My own manhood gave a definite twitch at the erotic picture that evoked. "Or into whatever opening was to be used." This new image made it positively stand at attention! I was shocked that the thought of someone else with my wife could have that effect on me! "Um, I'm not sure... I don't think... Um..." I couldn't formulate any coherent thought. "Well, a pact like that couldn't hurt even if we never do anything. Just to be on the safe side, do you so swear?" "Um, yeah, I guess." "No. There can be no guessing. We have to be absolutely clear on this. To swear the pact I suggested, you have to say specifically 'I so swear'!" I gulped then said with a shaky voice, "I so swear!" She nodded decisively and said, "And I also swear to the same pact." She settled down and soon was breathing regularly in sleep, while my mind was in a whirl, and sleep was very slow coming. With that settled in Jeannie's mind, our sex life soared back to its previous frenetic level. Neither of us raised the issue for a couple of months while my waist gradually narrowed, my hips and fanny puffed up, and my bust increased toward a B-cup. The sensations from my budding breasts increased as well, and teasing my nipples became a regular part of Jeannie's attention during our lovemaking. Finally, one night after our customary euphoric activity, Jeannie broached the issue of my transition again. "Are you finally comfortable that the sex after transition will be as good as before? As good as I say it is?" I blushed again. "No, I'm sorry, not really. How can I be? It still bothers me sometimes. I so love what we do now that I hate to give it up for the unknown." "Time is running out, sweetie. You have progressed to the appearance of a beautiful woman, and the final step to complete transition could be made soon. A decision will need to be made in the near future. Is it time to exercise our pact?" "No! Maybe... I don't know! Jeannie, love, I am just so confused." In point of fact, fantasizing over what my wife had said before, her description of the consummation she used to define our pact, had fueled my arousal to unheard of levels over the past two months. "Patty, darling, I have no great desire to do such a thing, but I have convinced myself that I will do it gladly if you think it will help your peace of mind." "I just don't know! It scares me. I don't even know how we would do it!" Jeannie smiled a bit sadly. "I guess my girlfriend and I would go out clubbing, pick out an interesting but safe looking gentleman and take him to a motel room. Once there, we would proceed as we agreed in our pact. It shouldn't be too hard." "Oh, um, OK." I wasn't sure if I was agreeing it wouldn't be hard, or if I was agreeing to do it. A tear rolled down Jeannie's cheek, so I figured she took it as the latter. Friday rolled around and Jeannie took charge when I got home from work. We both bathed with sweet smelling bath oils, and ensured there were no stray hairs where there shouldn't be. She encouraged me through doing makeup, then donning stockings, sexy lingerie, a short, figure hugging black dress, and black stiletto heels. She looked fantastic in a very similar outfit in royal blue. She packed a few toiletries and some sexy nightwear into a tote bag. As we left we looked like girlfriends out for a carefree night of fun. But the butterflies fluttering in my tummy threatened to lift me off the ground. Jeannie drove first to a motel where she registered, paid for a room, and returned with the key. She then proceeded to a dance club we had visited occasionally during the time I was becoming comfortable going out dressed. That was months in the past, but it felt immediately familiar as we entered. We chose a table near the dance floor where we could see and be seen and ordered drinks. Over the course of the evening, we each were invited to dance by several men, and by prior arrangement refused none that were reasonable. We avoided men too drunk or overbearing or just plain unattractive. We were looking for the right man to complete the evening. Actually, I was too nervous to do the picking, and after a couple hours, Jeannie led a handsome man back to our table, and introduced him as David. He was about 6' 2", with a well developed physique. Jeannie had once more done what I had been unable to, and the choice was made. I knew she would have whispered in his ear as they danced, inviting him for some after hour's entertainment with the two of us. We drove to the nearby motel, while David followed behind in his own car, and then led him to our room. Inside the room, Jeannie suggested David pour wine for the three of us from the bottle in the mini bar, and pulled me into the bathroom. From our tote, she withdrew our outfits for the remaining portion of the adventure. Her baby doll was again royal blue, while mine was red. Each had a matching thong that we'd chosen specifically to be sure it would hold my secret out of sight between my legs. The nightie hid almost nothing, and I was very nervous walking back to the main room, partly because my developing breasts would be on display to a man for the first time, but I think more, because Jeannie's would be on display too. We accepted plastic cups of wine from David and stood before him sipping the wine in anxious silence for a few moments. The tent in his pants as he took in the view made me quite tense. David seemed uneasy as well, and had finished his wine in only a couple of gulps. When it was empty, Jeannie calmly took his cup, and set it and her half-full cup aside, and moved up to him slowly, with frequent glances at me. I was at a loss as to what to do, so I just sipped nervously as I watched. When she was close, and I had given no signs, she collected herself, reached around his neck with both her arms, and pulled his head down into a kiss. This seemed to release David from his immobility, as his hands started to wander over Jeannie's lush body. He gave me a curious glance, but I remained frozen to the spot. Both Jeannie and David were soon breathing heavily, and David guided Jeannie to the bed and gently laid her on her back. He stepped back to survey her obvious charms, and hurriedly began stripping out of his clothes. Jeannie looked toward me, and motioned me over. I moved reluctantly till I stood by the bed beside her. David had completed removing his clothing to reveal an impressive hard-on. Jeannie spoke up. "David, I hope you don't think this is too kinky, but Patty and I are a couple. We have a pact that the only way the other can make love to someone else, to cheat on our union, is if the other of us guides the initiation of the sex with her hands." David's manhood stood out even straighter, and he looked searchingly at me. Jeannie continued, "Patty, do you want this?" That pulled David's gaze back to her, and freed me from my paralysis. I quickly shook my head no, while David's eyes were on her. She gave a little smile and what seemed to be a relieved sigh. Then she looked back at David, as she slid to the side of the bed and stood next to me. "David, it appears that this will proceed a little differently than we thought." Leaning next to my ear, she whispered so he couldn't hear, "Patty dear, thank-you. But we cannot leave David in this state, or we might have difficulties." With that, she gently guided me to my knees, and gestured David to come to us. Grasping his penis gently in her left hand, she stroked it lightly a couple of times, then guided it to my mouth, and pressed it to my painted lips. I could not believe this was happening, but I felt Jeannie's hand at the back of my head as she pressed me forward, forcing his manhood between my lips. Leaning down, she whispered, "You have to do this. Please get it over quickly!" As if in a dream, my head started moving forward and back, partly of my own volition, partly encouraged by Jeannie's hands on my head and his cock. Blanking my mind of my shock and dismay, I started trying to pleasure David with my lips and tongue, taking a bit more of him in with each forward stroke. I heard a deep groan, and flicked my gaze upward to see his eyes closed, and a look of pure pleasure on his face. He bent from the waist and moved one hand to squeeze and excite my right nipple, while his other hand sought out Jeannie's breast to fondle and tease. Her moans added to his, and to the rumble in my throat as I tried to moan as well, but was muffled by his cock. Before long, David was thrusting deep into my throat, then froze a moment before pulling back sharply, popping out of my mouth just as he started pulsing globs of jism. The first landed in my vacated mouth, the next hit my nose, another splashed my forehead, and then weaker spurts found my chin then my baby doll where it lay across my breasts. David's accompanying grunts trailed off as his climax faded. Not knowing what else to do, I swallowed the slippery glob on my tongue, and pulled myself to my feet. Jeannie stepped forward as David opened his eyes, and kissed him passionately, before urging me toward him, and suddenly David was kissing me with just as much heat. When he pulled back from the lingering kiss, he said, "Thank-you, Patty. That was wonderful." Jeannie let him know the fun was over for the night as she guided me toward the bathroom by saying, "We have to clean up. You can just get dressed now and let yourself out." She paused a moment before pulling the door shut behind us, "Thank-you, David." I was still in shock over how the evening had unfolded, so Jeannie gently washed my face with a warm moist cloth and dabbed the jism from my bosom. Finally we heard the outer room door close. When I was cleaned up, Jeannie led me back to the bedroom, to the bed, and gently guided me down and covered me. She crawled in next to me and wrapped me in her arms. She whispered in my ear, "Thank-you for not making me have sex with him. I love you." I drifted off to sleep snug and secure in her warm embrace. I woke sometime later to the erotic feeling of someone massaging my chest. The growing feeling of arousal pulled me from the depths of sleep, and eventually I registered that Jeannie was fondling me, and I sleepily began to return her attention. As my awareness grew, my ministrations became more effective, and soon she was moaning in lust. I felt her lips on mine, then her tongue invaded my mouth, plumbing it's depths as if in search of sunken treasure. Her hand had moved the thong aside and was stroking me to hardness. Her efforts became more frenzied, and soon she rolled on top of me and plunged my stiff tool deep inside her. She rode me wildly, repeating the same phrases over and over. "God, that was so exciting!' "I was so wet just watching you!" "Where did you learn to suck cock like that?" "I love you!" "Watching you turned me on like nothing ever before!" I was in a daze. I didn't know how to handle what she was saying! She got excited watching me suck off another man? This was driving me crazy, and all the time her wild actions pushed me toward the summit, until I exploded inside her, and I felt her shudder through a massive orgasm moments later. For the next several days, our lives returned to normal, more or less. Occasionally Jeannie was more abandoned in her lovemaking, and I knew she was fantasizing about our encounter with David. Truthfully, I still got a thrill out of fantasizing how it would have been had I guided David into her hot box instead. Finally she broached the subject again. "Patty, have you made a decision yet? Time is running out, and you have to decide. I think you know what you want. You are just afraid to commit." I moaned in despair, "You know I'm just afraid to give up what we have together." "Hush! We won't give up anything we can't replace with something better. I guess we will have to go through with the pact this time." She sighed sadly. "Jeannie, I don't want to do that to you if it will hurt you!" "I know, sweetie. If doing it will put your mind at ease, though, I want to!" So that Friday night started out virtually the same as our last attempt that ended with David. This time I was not so petrified, and some time into the evening of dancing and drinks, I found a guy that managed to make me feel comfortable in his arms as we danced. At the end of our dance, I decided he was the one for tonight, so I stretched up and kissed him lightly on the lips before inviting him for a romantic evening away from this noise. He nodded, and I led Kevin back to our table, introducing him to Jeannie. She studied him for a moment, and nodded approval. At our motel room this night, it started much as last time, but I was not frozen to the spot. When Kevin had stretched Jeannie out on the bed and shed his own clothes, Jeannie made the same speech as she had before to David. Kevin looked at me expectantly, and I slid up to him, and reached out to touch his manhood that stood so regally before him. As I stroked it gently, I looked down at Jeannie. As I tugged Kevin's lance toward it's target, I saw a look of fear flash across her face that gradually faded into sad acceptance. Kevin tried to complete the coupling, but I squeezed him and said sharply "Wait!" I resumed the stroking, and he stopped moving just an inch or so from the prize. My mind was in turmoil, and I thought I saw hope flicker in Jeannie's eyes. I pulled Kevin that last inch and started stroking his cock head across Jeannie's outer lips. Within a few moments, both started moaning, closing their eyes. I knew I had to make the decision now. Stop or continue? Do or don't. Could I do this to Jeannie? Could I not? Somehow I had to know if what I was giving up would have a replacement in a new life as a woman. Without conscious thought, I guided Kevin's weapon into position and tugged it forward. Jeannie's eyes opened wide in shock, then drowsed almost closed as the feeling of fullness and heat spread from her center. I knew I had to observe her carefully, after all, since this was why we were here. My breathing was heavy as I watched Kevin set up a rhythm plunging into my wife, and then withdrawing, only to plunge again. Jeannie's face ran through a gamut of emotions to finally settle on a look of utter pleasure. Soon her hips were bucking in time, and her body began to glow with the look of a woman in lust. I studied her features, and her emotions as reflected on her face. She arched her back and shuddered, her whole body reacting to the orgasm that shook her. Kevin continued his rhythm, and soon Jeannie rejoined him. Kevin groaned and plunged deeply within Jeannie, causing Jeannie's back to arch rigidly once again. Kevin's deeply buried member started pulsing sperm into her depths, and a look of pure rapture flooded her face as she began to shudder through another climax. Kevin collapsed onto Jeannie, and she pulled his head to hers, initiating a deep passionate kiss, then suddenly rolled him over, keeping his softening tool buried deep within her, until he was an his back, and she straddled him. She started grinding her crotch into his, and moving in a way that kept him trapped inside her. It seemed like only moments later that she threw her head back and emitted a deep groan as yet a third orgasm ripped through her, whereupon she collapsed on top of Kevin's still form. A few moments later, Kevin rolled her off of him, and rose to clean himself off and don his clothing. I had stood frozen through most of this, soaking up the feelings that shone from my wife's face. When he was dressed, Kevin came up to my still motionless form and kissed me deeply, fondling both my breasts at the same time. He glanced at the bed and said, "Thank her for me when she recovers, OK? And thank you, too!" He kissed me again, and was gone. I covered my inert wife with a blanket and crawled in beside her, snuggling her to me. Sometime in the middle of the night, we had a repeat of our wild coupling of the time before, only now with her gushing profuse thanks for making her have sex with Kevin. I wondered what I had done as we both rose to a fantastic climax. As our breathing settled down, she queried, "Can you see now what I was talking about?" "I'm beginning to." "Well, Patty, hold onto your hat, cuz you aint seen nuthin' yet!" We settled into a pattern of continued frequent lovemaking on our own with a clubbing excursion every Friday. The next time, she guided Jim's stiff pole into my virgin ass, after erotically applying lubricant to me and to him. Initially there was considerable pain, but that soon faded and the pleasure spiraled upward till I came in my thong without ever touching my cock. The next Friday, we both chose a guy, and later that evening I urged John's member into Jeannie's ass, and then moments later placed Gary's into her mouth. It was quite intoxicating to watch her as she was penetrated from both ends. This session, I'm sure she climaxed at least four times. And so it continued for a few weeks, each time doing something different, but always only what each of us started for the other. Observing Jeannie had long since convinced me that where could be fantastic sex after my transition, but I was still reluctant to commit. However, not long after we passed my one year anniversary of dressing full time as a woman, we became aware of a change. I think it had been sneaking up on us, but it was so gradual, and we were too involved to notice. It became obvious when one evening in our usual lovemaking I failed to achieve enough of an erection to penetrate Jeannie. I chalked it up to tiredness and laughed it off. Jeannie's expression indicated she didn't think it was funny. It happened again a week later, and increased in frequency until I could not get it up at all. All during this time, Jeannie kept pestering me for a decision, but I would never commit to taking the final step or to starting back toward what I once was. Finally, after three weeks of no intercourse because I was unable to penetrate her, Jeannie told me it was decided. My no decision had in fact become a decision, because it was now too late. The hormones had done their job, and now there could be no return. A month later, Jeannie accompanied me to Colorado, and stayed with me as I took the final steps on my journey to womanhood. I am still not convinced that I was a woman in a man's body. I think maybe I was just a transvestite with an overzealous psychologist. But, that's water under the bridge now. And life isn't too bad this way. I still have a loving wife, and my career. I still love dressing in women's clothes, even if I really have to pass as a woman all the time, since that is what I am now. Six weeks after my operation, we were back in a club trolling for a likely candidate. Later, in the motel room, Jeannie took extreme pleasure guiding him into my new orifice, then sitting back watching me experience repeated orgasms that shook me to the core. Afterward she just smirked and said, "I told you so!" So she had. And she was so right! We've also learned how to pleasure each other with tongues, fingers, lips, teeth, vibrators, and whatever else meets our need. Our lovemaking is as frequent and as satisfying as before, if quite different. We have continued to follow the pact. We still remain faithful to each other within the constraints of our agreement. Neither of us has initiated sex with another person on our own. We do frequently find enjoyable temporary partners to let me penetrate Jeannie with a hot hard cock that I guide into her with my hand, or for her to do the same to me. But now there is a problem. See, there's this guy at work, Mike. We've been friends for months now, and often eat lunch together. We've started to steal kisses in the copy room occasionally, and have even had a few heavy petting sessions in the storeroom. I have this fierce urge to ignore my pact with Jeannie and carry this to another level, but still feel bound by our agreement. Several weeks ago I tipped Mike off about our clubbing trips, and that Friday he was my 'random' choice for the evening. Two weeks later, he was one of the two we selected, and then two weeks later, I chose him again. Sex, initiated by Jeannie with the random men we pick up is fantastic, but when it is Mike, it is different. It is deeper. It is fulfilling in a way I've never encountered before, even when I was first with Jeannie, back when I was a man. Love is just different for a woman, I guess. But that doesn't solve my dilemma. I think Jeannie has figured it out though, because tonight she was the one to pick Mike at the club. And once she had planted his cock deep into my cunt, she quietly dressed and left the room. Somehow I kept Mike inside me all night, being very careful when he went soft after a climax, and then teasing him with touches and erotic pillow talk until he grew hard within me once again. I was in heaven the whole time! But I don't know what to say to Jeannie when I get home. While I didn't break the letter of the pact, since she put him into me, and he stayed there from then on, I feel I violated the spirit, and I feel guilty about that. I look across at Mike slumbering beside me and feel a warm glow growing in me. Yes, he finally was too exhausted to continue. He pulled himself out of me and collapsed beside me as the dawn light started to penetrate the curtains. I too am weary, but my feelings for him and my turmoil about Jeannie keep me awake, staring into the face of the man I have come to love.