I Make Believe I'm a Cuckold Ch. 04

Oh, I learned a while ago that Paul Terkin got fired after the security department reviewed old CCTV footage in the Seattle Field Office. He might have fought the charges if the tapes had shown him having sex only with Nancy, but because his homosexual activity with me was also on the tape, he didn't dare fight the charges. His wife, whom I never met, is filing for divorce. I liked Paul, and have made tentative plans to go visit him out there on the West Coast later this year. I'll bet I can cheer him up. He's still the best kisser I know.

You may be wondering how I'm doing, especially now that both Sally and Nancy are spending most of their time with their new men. Nights and weekends I dress in women's dresses and skirts all the time now. When I'm in the office I sport a very androgynous look. I've grown a ponytail and wear pants suits with an open blouse.

I've made no attempt to "pass", and almost everyone I meet for the first time assumes correctly I'm a man dressing in a feminine style without exactly cross-dressing. No skirts or dresses yet for the office. Maybe someday.

I've consulted with both the corporate HR office and a private employment attorney, and have made arrangements to transition to female in a year or two. To that end, I see a counselor regularly and take feminine hormone pills daily.

My little chest buds aren't quite breasts yet, but they're bigger (and better) than man boobs and are starting to reshape the lines of my clothing. Whenever one of my sex partners sucks my nipples I feel tremendous sexual excitement. I struggle during the day not to play with them myself. I have to give women a lot of credit for being able to go through the day without constantly teasing their own nipples. It's quite addictive.

It isn't always a rose garden back at headquarters. While the institution dealt with me fairly, in full accordance with regulations, some of the men in the office could be cruel and vicious. The men often openly discussed who'd had sex with me, or my wife, or both. They pretended that "both was best" and encouraged anyone who had not yet achieved "doubleheader status" to pursue the goal.

Men who were known to have had sex with me but not my wife were slightly suspect of being a bit light in their loafers, and Sally would cruelly withhold her pussy from them just to prolong their torment. On the other hand, men who had pleasured my wife and had no interest in male-to-male sex were goaded into giving it a try just so they, too, could claim "the two-fer."

***

I still travel about once every month. The office has struggled to manage the staffing for my trips because there are a few married employees whose spouses won't let them go on the road with "that freak." I'm very fortunate that three of our best younger employees are open-minded enough to bite the bullet and come with me. I know that in Tom Anderson's case he hopes working with an experienced older veteran of the organization will help his career.

He told me this quite frankly when I interviewed him for the opportunity. I have no hesitancy now to speak openly about my situation and asked him if my notoriety would cause him any difficulty. He assured me that none of the rumors about me bothered him at all and that he would value the professional opportunity to do fieldwork with an experienced hand.

Our first night in Detroit he paid an unexpected midnight visit to my hotel room and offered me the opportunity to put my experienced hands all over his cock and balls. He was one of the first men to teach me how wonderful it could be to have my nipples gnawed. But he also prefers the position where he hoists my legs up until my knees are in front of my eyes, my cum-hole is pointed at the ceiling, and he can "pile drive" down towards the floor.

I'm not enough of a masochist to truly enjoy this, but sometimes that's just the price a girl like me has to pay to get thoroughly fucked, am I right?

The next three nights he came to my room overnight and I taught him what little I knew about how one man can please another by submitting to him totally and without reservation. I have to give Tom credit for not blabbing about his conquest all over the office when we returned.

***

A few weeks ago, on my field visit to Dallas, one of our largest offices, I was accompanied by two assistants. Chuck was a married man close to my own age, and Barry was a new hire fresh out of college. The awkwardness at dinner the first night was quite noticeable, and I was unsure what the problem was.

I mean, of course, I knew there was some possibility that I was the problem, and that they felt awkward being in a hotel with a famously promiscuous sissy. My clothing choice for dinner may have raised the pressure, too: the lines of the brassiere I was wearing were obviously visible through the tight polo shirt, and that undoubtedly added to their discomfort.

Chuck finally started to speak. "Don, Barry and I have been talking about our plans for this trip."

I remained silent.

"There's a lot of talk back at the office about your, uh, your, what's the word, your complicated situation."

"It's not really that complicated, guys. I'm still a man, and I have all my original equipment. I enjoy wearing women's clothes, especially underwear, but I pee standing up just like you do."

Barry blurted out "But Mr. Elliott, you have breasts. That's kind of complicated, isn't it?"

"Maybe for some people. I might want surgery someday to make me a real woman, so there are hormones I have to take now to prepare my body for the possibility. The hormones give me breasts. The medicine I take now keeps that possible future operation an open door for me to go through - maybe - later on. But I also might never do that - I kind of like my dick, you know? It would be hard to get rid of it forever, and I may not."

No one said anything for a few moments. We sipped our drinks and each waited for someone else to continue the conversation. I kind of enjoyed the opportunity to express my true feelings for a change. But after about 15 minutes of talking about everything other than me, Barry broke first. "Mr. Elliott, can we see them?"

Chuck gasped slightly in surprise. He'd been thinking it too, of course, but he never would have said it.

I knew exactly what Barry meant but wanted to make him work for it. "We who see them what, Barry?"

He looked like he'd just swallowed a pickle. He did not want to spell out the kinky request to ogle his male supervisor's hormone-induced tits.

I turned to Chuck and repeated, "We who see them what, Chuck?" But for Chuck, I said it with a big smile. He understood that I knew what they wanted, and he was fairly sure I'd agree. He was mature enough to know that this way of saying "of course you can, but ask nicely."

"You know very well, Don. Barry and I have never seen a man with breasts before, and we'd really love it if you took us upstairs and showed us your new puppies."

I sipped my drink silently and tried to furrow my plucked brow to act like I was undecided. I kept them waiting at least two full minutes, which is, believe it or not, a painfully long silence.

"You two pay for dinner. I'm going up to 416 to get pretty for you. I've got a new lipstick and I want a real man's opinion about how I look. I'm going to shuck the polo and chinos, too, and pick out a nice nightie. Come up in 20 minutes for your private puppy show. If you're not there on time I'll lock the door and you might never find out what my teenie-weenie breasts look like."

And with that, I slid back my chair and went to the elevators.

About an hour later I collapsed in a sweaty heap on the bed between them. Young Barry had been a disappointment, unable to get it up for a second fuck after he inseminated my ass doggy-style. He also resisted kissing me, very obviously uncomfortable when I turned my head and tried. I had to settle for him tentatively biting my shoulders, especially as he blew his load into my milking rectum.

Chuck, on the other hand, followed Barry's screwing with a bravura missionary reaming with lots of kissing. With my arms and legs wrapped around Chuck, his tongue sucked hard into my mouth, I had my own orgasm, shooting my jizz between our tummies.

Barry watched from a chair, visibly affected by the profoundly different gay experience. Having a man bent over before you on hands and knees, his face and dick out of your sight, can make that position barely gay at all. Especially with me wearing a sexy nightie! But the blatant display of unrestrained missionary sex is a very different vision. My cute little cock was flopping around, and Chuck's shaft kept popping out into the light, and all that swapping of spit and hugging was just overwhelming for a first-timer like Barry to watch. A few minutes later, while Barry watched enviously, Chuck fed me his second load orally after I sucked him back to erection. I'd been wise to use 10 of those 20 minutes to douche.

I shooed them out of my room after that and took a nice bubble bath. I noticed that my legs and underarms needed a razor, but decided to ask Barry to help me with that tomorrow evening. I wanted to draw him out of his shell a little more. See, I was mentoring him already.

Tuesday night Chuck helped Barry with my grooming. The two sweet men carefully shaved me all over, working as a team. They knelt next to me in the big shower enclosure, each with a razor in their hands and their hands running up and down my legs and torso. Somehow all this relaxed intimacy made Barry open up a bit more to his natural inclinations, and he even kissed me right next to my landing strip when he thought he had nicked my skin with the razor. He looked up at me as if to seek permission, then repeated the gesture, this time keeping his lips against my skin longer while maintaining eye contact.

I reached down gently, took his head in my hands, and brought those curious lips in front of my half-hard penis. "Anything you want is OK, Barry. Try a little of everything and you decide what you like. I'm not going to get any harder. That doesn't mean I don't love your mouth; it feels delightful. But hose hormones trade my balls for my breasts. I might not even cum."

He accepted my offer and slowly sucked my cock into his virgin mouth. Barry had no idea what to do with a cock in his mouth, so I moved his head slowly up and down my shaft. I didn't get any stiffer. Chuck reached around to hug Barry and encourage him in his tentative exploration of fellatio. Chuck reached down to fondle Barry's erect dick and furry balls.

"Chuck," I said, "can you show Barry how to really suck a cock? Use your mouth and show him what to do with his teeth and tongue."

Barry pulled his mouth off of my sad excuse for a male organ and stood upright.

While Chuck had been the top with me the night before, he slowly went to his hands and knees and sucked Barry's hard cock into his mouth. Barry's gasps made it clear that he relished being blown, and I wondered if this was another first for the young man.

I dripped some shower gel down the center of Barry's back and reached down to rub it around his ass. When he didn't protest, and as Chuck continued sucking him, I added more gel and tickled his hole with my fingertip. Eventually, I inserted my pointer finger up to the first knuckle into his tight young anus. His brownie button was clenched really tightly closed, and I had to work hard to get into him even a little bit.

I assumed his groans were of pleasure, so I stood behind him, lubed my now harder penis, and snaked it up and down through Barry's butt crack, rubbing over the rosebud on each stroke. Sometimes I bent my knees and passed through happy valley from front to back, and sometimes I started on tiptoes, pointed my erection downward, and slithered towards his scrotum. He loved all of it.

I hugged him tightly from the back and pinched his hard little nipples as Chuck maintained the suction on Barry's dick. Then I called an audible and said, "Chuck and I are going to trade places now. I'll just die if I can't suck your beautiful cock, and Chuck for sure knows his way around a boy's asshole. This is going to be the best day of your life, trust us."

As I went to my knees and slowly spun Barry around to face me, I handed the bottle of gel to Chuck and said, "Baby steps, Chuck. You're getting a virgin tonight. That's a special responsibility."

He coated his firm erection with the slippery gel and ran a finger, then two, up into Barry. When he slid in, very slowly, Barry whimpered and trembled in my arms and mouth. But he didn't complain.

I'd taken cock up my own ass several times by now, and I know what felt good and what hurts like hell. I didn't know if Chuck understood how much tenderness mattered for a man giving up his manhood.

I needn't have worried. Chuck slid just the head of his dick inside Barry's sphincter, and then withdrew, In and out. No plunging, no shafting, just opening and closing his rosebud.

When Barry said "That feels so good, Mr. Elliott," I thought for a minute he meant my tepid blowjob, but then realized he meant losing his cherry. In a few minutes Chuck was fully hilted in Barry, but while his strokes were full-length, they were still slow and easy.

I stood up and began to caress Barry's nipples and stroke his face gently with my hands. I wanted to calm him down, to steady him for the excitement to cum when Chuck blew his load into the young man.

"Barry, Chuck and I are going to bend you forward now. Put your hands against the wall and bend at the waist. There's another inch or two of cock we need you to take, and then I promise you the orgasm of your life."

I used my hands on Barry's chest and back to bend him forward until he could reach out and steady himself against the wall. There was no need for Chuck to say anything, or change his gentle thrusting. In his new position, Barry's buttocks spread open much further and Chuck finally reached the far end of Barry's rectum. Changing his angle only slightly, he repeatedly poked our coworker's prostate.

Barry started blathering his impending release. None of it formed a sentence. "Oh my god. My God. That feels so. Fuck. What are you doing to me? Jeez. Here it comes. I'm going to cum. Fuck me. Shit. I think. That feels. I'm coming."

I reached across his arm, grabbed his chin, and turned his face to mine. I kissed him hard on the lips. His mind wasn't in it, and he didn't respond. His brain was all down in his asshole right now, and I'm not sure he even paid attention to my kiss. He pulled back to end it.

So I dropped to my knees in front of him, my back to the wall, and said "Cum. Let it go. Give me your cum. Chuck is going to fuck the cum right out of you for us."

I barely had time to stop talking and start sucking when he jerked his hips violently several times, either to get Chuck all the way in or to enjoy. I grabbed his hips to steady myself. Barry's moans got louder as his stretched little anus puckered and released on the shaft of Chuck's cock.

Barry came first, shooting a large load of sperm into my thirsty mouth. I held it a few seconds, and then swallowed Barry's virginity down into my stomach. When he came, his hot little hole pinched Chuck's shaft harder than ever and Chuck announced his impending ejaculation. "Up your ass. I'm loading your hot ass, Barry. What a sweet tight ass."

But Barry collapsed from all the excitement and fell to his knees right in front of me. His arms came down the wall to rest on my shoulders, and we held each other for just a second or two.

Chuck said something, I don't remember what, but I looked up and saw his steaming hot cock bobbing around in front of me. I craned my neck upward and sucked his cock into my mouth. Thankfully, it did not taste like shower gel, all of which had been scrubbed off by Barry's clutching rectum. It briefly occurred to me that it tasted more like Barry than it tasted like Chuck, but then I blew my load hands-free as Chuck washed my tonsils with his enormous load.

In good natured jest, he said, "Barry, that load was supposed to be yours."

Barry looked puzzled and, careful not to lose any cum, I tried kissing Barry a second time. There was no resistance at all now, Chuck had fucked all of the macho out of him along with his seminal fluid. I snowballed much of Chuck's slime into Barry's hungry mouth as we knelt together at Chuck's feet, nibbling each other's cummy lips.

I made sure that my next trip was with the same travel team and, when I later stopped hitting the road, Chuck continued to travel with Barry, who soon had his own collection of ladies' frilly underthings. I bought most of them after we moved in together.

***

Sally divorced me soon after the Dallas trip and Frank Malone has now moved into her house. I share a rented apartment with Barry, who has taken recreational cross-dressing to a higher level than I ever managed. We lay together at night, he with the nicer negligee but I with my C-cup breasts, and we love each other to death. His penis still works, unlike my little guy, so he gets to do all the fucking in our bed.

Barry lets me spend every other weekend sleeping with Nancy and Brad. She's still the only woman I enjoy kissing. One of my favorite things is to be wrapped in her arms and legs as if we were fucking in the missionary position. We get my floppy cock between our pubic bones and rub against each other while Brad reams my hole with his big cock.

Thanks to the hormones I now have real breasts for Brad to squeeze while he rides my ass, but my cock is now so shrunken that it only leaks cum when Brad or Barry fuck a load out of me, banging my prostate with the heads of their dicks.

I pay Barry back for my slutty nature by letting him travel with Chuck. I don't mind sharing him at all. Relationships like these need a slack leash and a lot of trust. Barry's a natural switch and enjoys taking dick from a real man as much as he enjoys making me a make-believe woman. Barry makes me happy, and the kid is entitled to some cock up his ass once in a while if he needs it. And I think Chuck is teaching Barry to be a more accomplished lover.

It helps me to frame it in old familiar terms: I'm sort of a wife to Barry, even though he's such a fag, and that means when he's on the road, on the bottom, with Chuck, I'm still a make-believe cuckold.

***

I rarely ever think about Sally anymore, or my years as an unhappy husband. I'm well rid of her, I think. Nevertheless, the Christmas visit last month to my family without her was awkward. Any family feels a slight ache for an empty chair where someone used to sit. Sally sat at their table for almost 10 years, and had always gotten along well with my family.

Dad and Mom were unusually morose all through dinner. Neither one made much effort to keep our conversation going. They seemed so sad.

But it wasn't just the empty chair that was causing my father's subdued sadness. I now knew, because Sally had delighted in telling me, that one reason Christmas at my parents' house had always been joyful was because the bitch was blowing my father. Every year, all week, twice a day. My gray-haired old man was apparently quite a stud. Who knew?

Sitting there now without her, knowing my dad was thinking of his lost blowjobs, made for difficult conversation.

Later that night, as I lay alone in my bed, my father came in fresh from his shower. And yes, just like in Sally's "Meet the Parents" story, all he had on was a damp towel. I couldn't imagine what he wanted to discuss, or why he didn't put on his pajamas. At least I could pretend I didn't know what he'd done with my wife. He may have cuckolded me, but as long as I acted oblivious we could continue to be father and son.

That plan instantly failed. He stood next to my bed and said, "Your whore ex-wife phoned me last week. She wanted to let me know she told you about us. Our blowjobs. I always suspected she was just too much woman for you."