I Make Believe I'm a Cuckold (Ch. 4)
This is the fourth and final chapter. This chapter contains a scene of incest between two adults.
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Friday would be our last day visiting the Seattle Field Office, so on Thursday Nancy and I spent the afternoon on our laptops at the hotel, preparing slides and spreadsheets for our visit report. We got all of our dreaded paperwork done despite Nancy twice ordering a break so that I could eat her pussy in the bedroom.
She had become quite a fan, even when it did not involve "forcing" me to "clean up" after a bull had inseminated her. Nancy had also started calling me her husband or referring to us as married, even when there was no one else there. Something vague and hard to define was happening between us, and I'm not sure what to call it. If we were children, I'd say we were "playing house".
Thursday night we had dinner with Cameron and Jordan at their apartment. Our Wednesday night frolic with them had lasted all night and turned into a four-way sleep-over. We were all looking forward to a repeat, although we told them in advance that we needed to sleep at the hotel our last night in town and would have a self-imposed midnight curfew.
Jordan was a terrific cook and threw together a delicious light meal. Cameron was the house wine expert and served several glasses of both red and white wines to pair with the food. We were all enjoying the meal and the company so much that I decided to let my guard down: I confessed that Nancy and I were not, in fact, a married couple.
This naturally led to a wide-ranging discussion about kinks, and role-playing, and keeping a relationship "fresh." They seemed puzzled why Nancy wanted men she picked up to think she was married. She tried to explain the separate thrill that was "cheating and getting away with it." She told them that we were going to maintain the fiction 24/7 now, with or without an audience.
They were both single men and had questions for us about marriage and divorce. Because Cameron was completely straight, and Jordan was unambiguously gay, they'd never before shared any physical intimacy. Screwing me and Nancy side by side last night was the only shared sexual experience they had, and they'd enjoyed it a little bit.
They thanked us for introducing them to a previously unexplored area of their own different sexualities. They both hastened to add that it wouldn't change the sexual incompatibility that made them possible roommates. Nancy, always a bit quicker than I am, told them that in the beginning, she and I had our own sexual incompatibility that made sex between us unlikely. Until it didn't.
It was Jordan who impishly said that perhaps if they dressed me up in ladies lingerie Cameron would be willing to push the envelope a little bit. He said he would help Nancy shave my body hair like we had discussed the night before. Jordan added that Cameron often boasted he had quite a collection of abandoned panties and bras in his "trophy drawer." Nancy and the boys could dress me like a woman with those.
So, off to the bedroom I went. Cameron stayed behind to clean up while Jordan and Nancy took me into the bathroom for my "makeover." By the time they had finished with me, I'd been smothered in depilatory cream and rinsed, then shaved. Finally, they dressed me in a bra and panties, and lightly shaped my eyebrows. Of course, they had no wig, but Nancy contributed generously from the cosmetics in her purse. Donna had never looked better!
We hadn't really thought this through. We discovered right away that Jordan was initially less interested in me now that I looked vaguely feminine, yet Cameron hadn't yet decided I was woman enough for him to get over his homophobia.
It was up to Nancy to get things going, so she started calling me her lesbian girlfriend "Donna" and ordered me to eat her pussy. (Again. My mouth muscles still ached after eating her to climax twice this afternoon.) Nancy then made a big show out of pinching my nipples and ordered "Donna" to suck Cameron's cock.
I sensed that I would need to urge Cameron on. I told him that I had lost my girlie virginity a few nights before when Paul Terkin had "made me a woman." I then put my head near his and whispered to him "I'm not a man anymore, Cameron. Not really. I have a little penis but I'm sort of a woman now and just want men to give me their dicks. I know you're new to this and aren't comfortable yet, but may I please ask you to let Donna suck your beautiful penis for just a little while?"
He remained motionless, but I took that as a willingness to proceed and slithered down his body. I sucked one of his nipples for a few seconds and then very slowly lowered my face into his crotch, taking half of his cock into my mouth.
Cameron had severely trimmed his flaming red bush of pubic hair back to a low-pile carpet. His manly scent was still powerful, but nuzzling the base of his cock and under and around his balls was much more pleasant for me. He quickly erected, which seemed like a good sign that I was now sufficiently girly in his mind that he was aroused.
"Cam," Jason said, "can I show your girlfriend Donna about anal sex?"
Cameron had his head back and his eyes closed, enjoying the fiction that a woman was sucking him off. "You stay away from her pussy, but you can do anything she lets you do to her ass." I knew what he meant. Pretending I had a pussy helped him enjoy the blowjob he was receiving from "Donna."
Jordan got plenty of KY Jelly on his finger and slowly opened my anus. Despite the pounding my ass had taken before, it was fairly tight. A second very lubed finger spread me wider. Then some KY was pushed into my bottom, his fingers made two or three augur-like movements, and Jordan was ready to teach Cameron's new girlfriend what anal sex was all about.
I played my part, raising the pitch of my voice and pretending to be a woman. "No, I've never had anything there! You can only fuck my pussy."
"I'm not sticking my nice clean cock into that slutty cum-hole, you skanky bitch. Who knows how many diseased dicks have been in your cheating pussy. We're doing this my way, into your virgin asshole."
I trembled with delight as he gently inserted his rigid fag-tool up my rectum. Jordan's dick was exactly the size I liked best – long enough to fill my rectum and bash my prostate, but not such a monster as to go all the way through to my bowel. He moved in and out slowly, which I also preferred, but right at the end of his insertions, he made a point of smashing his pubic bone against my buttocks as he drove in that final inch. This rough physicality punctuated the end of each tender stroke. He drove me crazy with lust. Slow, gentle, bang. Slow, gentle, bang.
Jordan had my "Goldilocks cock." Not too big or too small or too thick; none since has ever been quite so perfect for making me squeal while curling my toes and dumping my jizz into the bed linen.
"I confess I miss the tiny extra thrill of thinking we were making him a sissy cuckold," Jordan said.
Cameron chimed in that making love to Nancy the night before while thinking her husband was impotently watching was the wildest thrill he'd ever had. "Next woman I look for will definitely be married."
They exchanged a few more remarks about the now-dropped "slut and cuck" role play Nancy and I had performed. "How about you, Don?" Jordan asked. "Don't you miss being a cuckold?"
I did a bit. Sex with my "wife" Nancy contained a frisson of depravity that sex with my coworker lacked. The contempt of the men she seduced had given me a dirty thrill.
Nancy, sitting quietly, reached into that big purse of hers and took out her iPad. A wicked idea had occurred to her.
"Don?" She called my name and I lifted momentarily off of Cameron's generous erection to look her way. "I think you've been a bad husband tonight, Don. You've been the bestie-best girlfriend I've ever had, and you're a special nice girlfriend for Cam. But you haven't been a very good husband, have you? You forgot to FaceTime with Sally. Remember her, your real spouse? She would love to see your underwear now, wouldn't she? If she knew you were being such a good woman for Cam, wouldn't she want badly to see you?"
Nancy and stared at each other for just a second, but I knew what she was suggesting. I wasn't a very smart guy. Hell, not even a guy at the moment, what with dicks at both ends fucking me like a tramp. But I wasn't such a dimwit that I failed to realize that Nancy was asking me to make a decision that would affect the rest of my life: who was I, and who did I wish to be?
I paused one or two more seconds and then silently nodded my head. Nancy grinned wildly and pushed a few icons. Within seconds, we heard that annoying boop boop tone FaceTime makes before the other party accepts the call. When Sally did pick up, we had audio but no video and I heard my wife hushing someone else in the room with her. Nancy told her we had no video, and in another 10 seconds, my wife's face appeared.
"I wasn't expecting a call this late Nancy. Is Don OK?"
"Your husband Don's not available now, but my girlfriend Donna is. A really nice young man fucked me senseless last night, so Donna is saying thank you. She's got a mouthful of his dick right now and can't talk, but here, take a look." She pressed the icon to switch the camera.
My wife was silent for at least five seconds, which felt like an eternity to me at the moment. "Oh Don, you look so beautiful like that. Will you dress like that for me when you come home? I just love your brassiere. Does it hold your little man boobs snugly in place? Nancy, who is that other man with the beautiful hard cock fucking my husband?
"I'm Jordan, ma'am. Nice to meet you. Thanks for letting me use your sissy's asshole."
"Hi, Jordan. That's so great for you guys. The top half of my husband is a cock-sucking female named Donna, and the bottom half is a sissy faggot with a tight asshole named Don. Hope you guys are enjoying this. My husband is such a hot whore for cock; I'm learning more about him every day, it seems."
"Sally," Nancy said, "Cameron just told us that last night was a teensie bit more fun for them because they thought Don was my cuckold husband. They're a little disappointed to think that Don isn't a cuckold. Can you think of anything that would cheer them up?"
"Oh, Cameron, that's so sweet," Sally replied. "Fucking a cuckold's ass is so special. I almost wish I was a man so that I could know how good it feels to just fuck the manliness right out of a cuckold. To turn the shell of a man into a sissy while its wife watches, and doesn't mind losing her husband, because he was never really a man anyway."
My wife continued, "Right, Donna? You were only making believe you were a man. You knew deep down inside, or way up inside might be more accurate, you knew way deep up inside your faggy ass what we all know about you. It was so hard to pretend to be a man, and now you don't have to, and that's all thanks to Nancy making you pretend to be a cuckold."
I trembled, ecstasy and humiliation washing over me in equal measures. Sally had always known me better than I knew myself. There had always been a woman inside me, and if a man went inside my body at either end he would find her and release her.
Sally finished by saying, "Everyone says Donny did a great job pretending to be a cuckold. But from now on it will be so much easier, you worthless sack of shit. Here, Donna Elliott, look at this."
Then, to someone off-screen, she said: "take this and flip the camera." The next thing I saw was the head and torso of Brad Rogers, the young guy who worked in our mailroom, shirtless and sweaty. He backed up a few steps and pushed the button to flip their camera, and there was Frank Malone plowing Sally's cunt doggy-style on her bed.
I completely stopped sucking Cameron's cock as I stared, shocked, at the tablet. Sally's thin face and messy hair suggested she'd been actively fucking my colleagues for some time tonight. As Frank picked up the pace and resumed pounding my wife's crotch forcefully, her whole body jerked forward and rocked back, but her small A-cup breasts barely moved at all.
Brad found a way to prop up the iPad in Sally's bedroom and then moved around into view a second later. He was completely naked and brought his substantial erection next to my wife's mouth. Of course with her head in constant motion, he couldn't get my wife to suck him just yet, so he just slowly stroked himself.
"This is a "Neapolitan, Don. You know that ice cream with slices of vanilla, strawberry, and chocolate? I'm the vanilla, and Sally's fantastic holes are the pink strawberry, and Brad here is obviously the chocolate. If you stick around a few more minutes you can watch Brad and I show you how we make a Neapolitan for your lovely horny wife."
And with that, Frank withdrew his cock from my wife's pussy and lay down on the bed. Sally wordlessly mounted him, sinking down on the full length of him with a satisfied groan. She humped up and down a few times to get herself settled, then stopped and leaned forward over Frank, kissing him passionately.
Brad slathered lube on his coal-black shaft before entering Sally's obviously experienced anus with his own satisfied moan. Only Frank watched me. Brad was reaching around Sally to maul her little tits and vigorously pinch and pull at her nipples while sliding in and out of her anus. He bit her shoulder, hard, and she screamed some weird kind of pleasure.
Then the blissful face of the woman I'd married faced the camera again and spoke to us. "See, Cameron, Don and Nancy told you half a truth. The wimp with your cock in his tonsils is a cuckold after all. Mine. He has always been my cuckold, he just never knew it.
"See, Don, why I never complained about all your traveling? Your friends take such good care of me when you're gone. You and I are going to thank them appropriately when you come home. Not just Frank and Brad. Although Frank is my best helper who comes right over before you've even had time to board the plane. I love his cock between my legs while you're still sitting in the departure area. We pretend he's a first-class passenger, and he always boards right away, before you do. So many men in your office have been so helpful when you're away. I guess I should make a list for you when you get home, so you can thank them personally one by one. The way you're thanking Cameron and Jason right now, I guess."
Jordan's cock pulsed and throbbed in my ass. When my ring clenched down on it tightly he exploded inside me. I could feel his dick buck and ejaculate his first load of the day up inside me as my sphincter nibbled at his penis as if trying to chew it.
As Jordan settled down and ceased moving, Cameron blew his load into the front of my mouth, where I could relish the flavor. As I swished and then swallowed gratefully, my own worthless little cock emptied my prostate gland all over Cameron's leg.
"Make sure the worthless faggot cleans up his mess, Cameron," Sally said. "Tell him to lick his worthless fairy juice off of your body.
Then, just before Nancy ended the call, Frank Malone said, "Love the girly underwear, Boss. Brad and I can't wait for you to come home. We've been talking to your slut wife here about how much fun it would be to do this with you for once."
The two or three months after my Seattle trip was the most exciting time of my life. At home, Sally and I opened up to each other in every way, and we accepted each other for who we really were. Sally was now free to be a promiscuous whore with a ravenous appetite for cock, and I could live openly as a submissive cross-dressing bisexual bottom for dominant men and women. At home, we never slept together and we rarely slept alone.
Frank and Brad enjoyed taunting me while I sat in a chair in Sally's bedroom watching them just fuck the shit out of her, sometimes quite literally.
Despite the big talk, however, Frank barely ever let me touch him. He says he's just too much of a man for "bi cucky shit". Like Cameron had once been, Malone was averse to anything vaguely gay or bi that would compromise his self-image.
Only if Sally asked would he lay back on the bed, legs over the edge, and let me kneel between his knees to suck his cock. I had to promise not to touch him, or even speak during these blowjobs, so as to allow him to pretend that it was a woman cleaning the pussy slime, or worse, off of his penis. Once in a while, when I performed wearing a brassiere and panties, he would reach down while I sucked and pinch my nipples.
I was astonished to learn, one at a time, which of our friends, neighbors, relatives, and co-workers had fucked my wife behind my back all these years.
I think the one I least expected was my father, a 68-year-old accountant with a bad knee, upon whom my wife had been bestowing regular blow-jobs every time we visited my parents at Christmas. These had started years ago after she accidentally bumped into him coming out of the shower one night and his towel slipped to the floor.
Sally told me that the old goat had quite an erection before he dropped the towel, but that he was limp as a noodle 20 minutes later when he slipped into bed with my unsuspecting mother. Sally said his annual cum shots are still her favorite part of the holidays.
I'm sure they're Dad's favorite part, too. According to my wife, my dad got a kick out of calling me a clueless cuckold while my wife bobbed her head up and down on his grizzled dick. She said he loved to make her say insulting things about my own smaller endowment while nuzzling his balls.
Sally said his cock really was twice as big as mine and wondered from whom in my family tree I had inherited my shrimpy penis. Sooner or later she hopes to seduce my two brothers, too. This year I am going to watch, and see if I can suck my old man myself. Just thinking about sucking the sperm that made me from the cock that planted me gets me hard as a rock right now. It would be even more fun if I did it in front of Mom....
There were at least six men in my office who had been visiting my home whenever I was on the road. Frank Malone was the closest thing Sally had to a steady boyfriend. He has a key to our house and comes over any time he feels like it. He may be around for a long time; too, because of all the men she has, he is clearly Sally's favorite.
I toss and turn in bed many nights unable to sleep as I watch them have sex on my iPad. Sally set one up in the bedroom sort of permanently and wants me to watch and listen to most of her romps if I am not included. Frank is quite an athletic lover and tosses Sally's skinny body around like a ragdoll as he fucks her. Many of his performances are choreographed for my discomfort, and he keeps up a running commentary of degrading things to say about me while he services Sally's insatiable body in front of the camera.
I haven't seen as much of Nancy as I would like now that she and Brad are living together. I get invited to their apartment about twice a month to join them for a threesome, but now that she has a steady man she doesn't travel anymore. She continues to be kind and tender with me, even though the nights I sleep over Brad spends most of his sexual energy on, or in, me. Thank God Brad is the anti-Malone. He just adores "bi cuck shit".
He loves to tease her that I suck his dick much better than she does, and I work hard to make that true. I have to say that one of my most pleasant experiences is when Brad eats his own loads out of my abused anus after fucking me. Nancy flat refuses to do that, the selfish whore, even though she makes me eat hers, from whichever hole Brad unloaded in. Brad enjoys dressing me up in ladies' lingerie and fucking my lights out. Personally, I think he's almost as gay as Jordan, just deep in his closet, and I don't mind a bit. Nancy's tired old cunt can use the rest, those weekends I'm sleeping over, and she has no trouble getting off when I eat it.
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 lot of slack leash and 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."
"Dad, what's past is past. Sally sucked and fucked a lot of other men, and I let her do it way too long. We're both happier after we split."
"You don't understand, boy. I don't give a shit if you're happy or sad. I just know my cock is sad."
"Dad, it's probably a good thing it's over. If Mom found out you were cheating on her she...."
He cut me off mid-sentence with a hearty laugh. "If your Mom found out? Your Mom was fucking thrilled some other bitch drained my oil. Margaret would have paid Sally for swallowing my loads for the week. Your mother hated even the thought of a dick in a mouth. Married almost 50 years and she never once let my dick near her mouth. Not once."
Before I could completely wrap my head around this, that my wife sucked my father's cock with my mother's approval, he dropped the bomb.
"Margaret thinks sticking a man's piss stick into another person's mouth is nauseating. So when Sally told us our son was a cock-sucking faggot who wore ladies' bras and stuff, we were kinda unsettled. It was hard for your Mom to pretend all night at the dinner table that she didn't care."
"Sally told you I'm bisexual?"
"I'm not sure your mom and I know what a bisexual is. I think the phrase Sally used was 'cum-addicted faggot slut.' Is that close to 'bisexual'? I know that sounds cruel, but she actually gave you a big compliment. She said she'd bet me $100 I wouldn't miss her at all because you suck cock even better than she does. Said I should do that towel drop thing and wave my hard-on in front of your face. Said you'd gulp me down like a thirsty fella at a bar, that you simply would never not suck a big hard throbber."
He dropped the towel. "Let's see. Open wide, pansy."
He didn't miss her at all that night, or the next three.
One fantasy I didn't realize right away was when Mom declined to watch us in bed. She said just listening to us through the open doorways was disgustingly perverted, and that watching a cock get sucked would make her vomit.
She didn't give in until the morning I left. She watched as I went to my knees next to my packed suitcases moments before my departure. We were in the living room, of all places, and my father was standing in his bathrobe as I plunged my face up and down his shaft.
He stood like a rock, one outstretched hand leaning on my shoulder as if holding me down. It was even more exciting than I had dreamed it would be to drink my unborn brothers and sisters from his big old grey-haired cock. In a strange way, dad's hand on my shoulder as I nurtured myself on the end of his big erection was sort of a benediction. I think he loved me, at least a little bit, as he dumped the final load into the back of my mouth. His cum was our connection to each other. I resolved to come home more often to visit them.
Mom had a look of absolute disgust on her face, but I noticed that she quietly rubbed her own crotch in her nightgown watching us.
When I tried a few minutes later to kiss her goodbye, she jerked her head sideways and slapped my face, hard. "I've never had a penis in my mouth," she snarled angrily, "and I'm sure not going to kiss a boy who has. Your wife was a nasty, evil cunt, but I gotta give her credit. She knew a fairy when she found one, and she was smart enough to dump your wimpy ass."
Then my mother closed the door in my face. The last thing I heard as I stepped away was her shout to Dad, "Put that fucking worm away, Harold. Christmas is over for you. You're disgusting, too."
Barry had sort of an intervention with me after I told him about fellating my father. He says he loves me dearly, but that I'd sunk so low that I was really crying for help. After further talks with the counselor, I decided I'm going to have the surgery next week.
Several of my coworkers have planned a low-key sendoff party for the night before. Each one will pose for a photo of them kissing my dick goodbye. We have a little pink ribbon ready to decorate my little soldier.
Wish Donna luck!