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Late Vocation By Gingerfred Man Chapter One - A Vocation Is Not a Vacation In the Catholic Church, a priest is usually ordained in his mid-to late-twenties. If he's ordained in his late thirties or more, it's said he had a "late vocation." It's the phrase I use to describe my transition to femininity. I was a "late vocation." Sometimes I regret that. I missed a lot in my first years . Mostly, I'm just glad I got my vocation when I did. At the age of 50. Days after my 50th birthday, and my second divorce, in fact. My name is Connor O'Hara. And I'm a pantyboy. Actually a pantyman, I guess, but let's not split hairs. I suppose you're thinking that I was one of those guys who secretly whacked off to "Panty Boy" magazine's delicious, young lovelies. No. I never saw Panty Boy until much later in life. And I never wore my wife's lingerie whenever she was out. Never really considered it. Was I caught in my frillies by my wife one time and "forced" to wear a cock cage and a maid's outfit while my wife and her lover fucked on my marital bed? Are there really guys like that? What a pile of crap! Anyway, as I said, I'm twice divorced. No kids. I take equal responsibility for that. I ran out of love with both wives just about the time they ran out of love for me. And then there was the whole nagging, manipulation and emasculation thing. They did that. Not me. Not that I was a saint. Anyway, I was in no mood to look around for strike three. I was through with women. For a while at least. But my private parts didn't like that life decision very much. I still craved femininity in my life. Thus, I still got nice and hard - seven inches worth - whenever I saw a pretty woman. Or a picture of a pretty woman. Or remembered having seen a pretty woman. So, of course, I hit the Internet and bought a case of Slickboy Masturbation Cream (a Spermbutt Industries product). OK. Internet porn. For the most part, ick. The videos were the worst. No one seemed that interested in sex. And who pulls out of a pussy or a mouth at the big moment to jerk off and shoot on a woman's face? More crap. Some of the photos and cartoons were pretty good, as were some of the stories. But most of it was really bad. Until, I took a chance and began looking at crossdressing porn. Why, I'm not sure. Odd curiosity, I guess. Some of that porn was pretty awful too. But some of it had me cumming hard. Here's why. The stuff I found showed guys, some of whom were older, my age and beyond, enjoying sex with each other. Really enjoying it! Some of the guys wore women's makeup, wigs, lingerie and stockings. Some kissed and masturbated other sissy men. Some of them let naked men put their cocks up their asses. Their asses! In two marriages and some heavy dating, I never had a woman who would let me do that. After a few days of binge surfing on that stuff, I had found my Rosetta Stone. Some of the pics had a logo for something called "Late Vocation." I looked it up. It was a national chain of clubhouses where members could sissy up and have sex with each other. Right there! In the club! Just like in the porn! The basic member fee was $500 a month. To keep the riffraff out. And make lots of money too. Lingerie and makeup and lessons in their wear were provided for the first month. Then it was BYO. The minimum age was 50. And they checked IDs! I was barely old enough. Was there one in my area? I looked. 3.7 miles from my house. Oh my Chapter Two - Clubbing Now I know what you're thinking. Did I fire six shots or only five? Wait. That was Clint Eastwood's line in "Dirty Harry." What you're thinking is, "Was Connor crazy? Did he think he could just join some club, put on stockings, a wig and a nightie and start sucking off some other, similarly-dressed, old guy's cock?" And I would understand your misgivings. If I were 30 again. Or even 45. But what the heck. Not much scares me at this age except that I'll miss out on things I would like to do because I'm scared to try them. Even better, by 50, I had made my money and, even with two divorces, I need never work again. Yes, sucking one's first cock is a big step. But I thought, I'll never know if I like it until I try. So with my ID, cash, credit card and checkbook in my pocket, I strode into my local Late Vocation chapter and asked to sign up. The person at the front desk was a man who was maybe five or six years older than I. And dressed as a woman. He didn't look weird to me, even then. Especially since he was so self-confident about how he looked. And I could see why. He wasn't exactly a dick stiffener. But he was kind of cute. Slim. Friendly face. Nice legs encased in silky stockings. Short skirt. And some skyscraper heels that he managed quite well. "Welcome to Late Vocation, sir. My name is Linda. I presume you know about our strict, age policy." "Yes," I said, and I showed him my proof of age. He looked at it, then back at me. It was kind of flattering. He didn't think I was 50 yet. I was being reverse-carded. Linda made a copy of my ID and handed it back to me. "How can I help you?" Linda asked, sweetly, but professionally. I cleared my throat. "I was thinking about joining the club. On a trial basis." Linda frowned. "We don't have a trial basis membership, sir. Everyone pays at least $500 per month or part of a month. But I would be happy to discuss what our club is all about with you before you sign up." I agreed that that was a good idea. Linda began with a series of questions. Marking down my answers. "How often do you wear women's clothes? Always, almost always, frequently, rarely or never." "Never," I shot back. Linda gave me a funny look. And went on. "Have you touched another man's penis? If so, how men? More than 30. 10-29. 1-9. None." "None," I admitted. Then Linda was really perplexed. "You know what we do here, right?" "I do. And I'm eager to learn." Linda considered me carefully. "Well, you are quite cute. And you would be our youngest member. But most men are averse to crossing the lines you say you want to cross. How about a simple test? Just sit in that chair. That one. Yes." Linda sissied over to me on her high heels. Standing in front of the seated me. I could see where this was going. She lifted her skirts to reveal a very nice pair of creamy, shaved thighs above the black welts of her stocking tops. And a skimpy pair of black panties over her garter straps. She locked eyes with me and lowered her panties. Setting free a nice, pink, erect, six-incher of an uncut cock. It looked very sexy to me. So sexy that I reached out and stroked it. Skinning back the knob's skin cover. Using my thumb to rub the "arrow point" under the knob. Linda liked that. And looked as if she were about to say that the test was over and I could join the club. But I was always an overachiever. So I took Linda's cock head into my mouth and used my tongue to give it a nice bath. Oh my! Linda LIKED that! I looked into Linda's eyes to make sure I was doing it right and I saw something I had seen far too infrequently with my wives. Lust! Not to mention that Linda's eyes looked pretty good, what with her careful application of mascara, eye liner, false lashes and eye shadow. Pretty good indeed. Linda didn't resist when I rubbed her ass cheeks as I sucked her off. She even squealed when I rubbed the pad of my right middle finger along the opening to her anus. I was just doing the kind of stuff that I knew I would enjoy. Nothing fancy. All in all, I was very much enjoying my first bit of cocksucking. And wondered why men didn't help each other out like that more often. I even enjoyed it when Linda grunted out something about how she was cumming and if I didn't want something or other... Too late. Linda shot her sperm right into my mouth. Not a lot of flavor there. But I really enjoyed seeing Linda so happy when I swallowed it all. I was a bit leery about her kissing me after, thinking that I might ruin my new vocation by not enjoying kissing a pantied, stockinged, made-up man. No worries there, I liked it very much. Linda was a good kisser. Better than my wives were. And I loved the feel of her lipstick on my lips. She was pretty good with her tongue too. Most of all, I think I liked what Linda was offering me. It was what I needed a lot more of in my life - femininity. In my opinion, both of my ex-wives ditched a lot of their femininity soon after the wedding. After a lovely 15 minutes of excellent, somewhat heated tongue-kissing, Linda semi-regained her professionalism, got off my lap, moved to her computer and signed me up for Late Vocation. Effective that minute. Chapter Three - Girlying up Linda seemed reluctant to escort me from her work area to the prep area where she said I needed to go next. Did she want me to give her a nice round two? Did she want to give me a nice round one? All was well when I gave Linda my cell number and told her to call me for a sweet get-together whenever she wanted. She seemed very pleased with that. She escorted me to the prep area, introduced me to Susan, the preparation specialist, kissed me with tongue and wiggled her way back to reception. Susan was different from Linda. She was clearly under 50 - perhaps late 30s. And I think she was a genetic girl, though one can't always be sure. Anyway, Susan was not interested in sex with me. Yet. Which was a good thing because she gave me three dizzying hours of instruction on make-up, wearing women's clothes, walking in three-inch heels and female mannerisms. Tough to absorb all that at once, but my attitude was that it's just like when you get your first driver's license. You only really learn to drive when you're on your own. Still. I liked the results. Considering that it was my first time, I looked pretty good. Susan seemed to agree. "if you do what I showed you, you'll be very popular with that bunch of sex degenerates out there," she said. "Heck, even if you don't do your makeup and all that well, they'll like you a lot." It seemed to be true. I wasn't looking as good as, say Jennifer Lopez on a bad day yet. But I was kind of pretty. And my newly-shaved legs, encased in some amazing, black, seamed, fully-fashioned, reinforced- heel-and-toe stockings, were smoking hot. Being a fast learner on physical things, I was good enough at walking in high heels that it made my legs and my ass look even better. Susan smirked as she watched me admire myself en femme for the first time. But the smirk turned to a smile when I tipped her $500 for her efforts. "If you need anything, you call me," my new, very good friend said. Then she led me on to another office-like room where I was asked to wait until the club manager arrived. Moments after Susan left me, the door opened and a slim, early sixty- something man wearing a tight, short skirt, great black stockings and big heels sissied in. "My, my!" the chapter manager said. "I had heard that you were hot, but not nuclear. My name is Brenda. Welcome to Late Vocation." I took the extended limp wrist and shook "her" hand. "Thanks," I said, "It's great to be here. What's next?" "That's up to you, Honey. By the way, do you have a girl name yet?" I didn't. But there was a name I always liked, "Colleen," I said. "Colleen O'Hara." "Well then, welcome, Colleen. Have you emptied your balls today yet, Honey?" A personal question. But relevant. "Not yet. Do you have any good ideas about that?" I asked, a little flirtatiously. "Well, as the leader of this fine group, I consider it my duty to ensure our new members receive a thorough briefing on what's available to them. So why don't you drop those pretty panties and stand steady on your heels. Can you do that? That's it. Very nice." It seemed that I was about to receive my first blowjob as a member of Late Vocation. I want to tell you all about it, but it occurs to me that I haven't told you what I was wearing. Susan had dispatched me in a white corset with six garter straps; a white push-up bra; skimpy, white bikini panties; brown, seamed, fully- fashioned, reinforced-heel-and-toe stockings; and white patent leather pumps with three-inch heels. Not bad. Brenda seemed to agree. She got onto her knees and, almost before I could get my panties down, she had my cock in her mouth and was giving me the best blowjob of my life. Slow, wet, tongue swirls around the knob as she penetrated my anus with one manicured finger - just to the depth of the nail. It was exquisite. Far better than the BJs I got from wife #1 on my birthdays and wife #2 on alternate anniversaries. And I wish I had been able to hold back for an hour or two so I could fully enjoy it. But I had had a LOT of stimulation that day already and I was only able to resist cumming for five luscious minutes and 43 delicious seconds. So far, Late Vocation was getting an A-plus from me. Especially since Brenda swallowed! Swallowed!! Another life first for me! And she seemed to savor every drop. Being a gentleman, I asked the lady if she would care for a bit of recompense. She stood, dropped her panties and smiled in response. I had a bit of performance anxiety when I took Brenda's pink stiffie into my mouth. She was the chapter manager and all. But I seemed to please her very much. Especially when I slid two fingers into her bumhole and rubbed her prostate as I slurped her pretty knob. Oh dear. Brenda blew a gusher! More than my unpracticed mouth could handle. Though I vowed to improve. Brenda seemed quite pleased. If her ferocious tongue-kisses after her orgasm were sufficient evidence of that. When all the aftershocks had passed. Brenda resumed her role as chapter manager. "That was extraordinarily delightful, Colleen," my new friend said. "But it occurs to me that you've been here since 9 a.m. and it's almost 1 p.m. Can I get us some lunch while I brief you on the benefits of membership? By that time, I'm sure we'll be ready to resume the benefits program we were enjoying just now." Great idea, I thought. And I said so. Brenda was pleased. "We have a first-rate food service here, Honey," she said. "Members charge food to their accounts, but this first lunch is on me. Just a minute." She got on the phone and ordered two girlie salads and a bottle of white wine, delivered to her office. While that was being prepared and delivered, she got out a map and showed me the layout for mature sissies to lay out. "I'll take you to all these places later today, but let me give you the big picture. Here is the dressing room, where everyone has a big locker to store the man clothes you'll wear to the club each visit and your feminine clothing, wigs and beauty products. "This is the gathering room, where the ladies come to flirt with their current and future friends. You'll note that there are ample couches and loveseats for members to get fully acquainted." I noted. "Here we have the ladies room - no icky urinals. And over here we have the love suites, which members can rent for up to 24 hours. Each suite is like a high-end hotel room, with king-size bed and bathroom with sunken tub. Very popular for those members enjoying a steamy love affair with another member and want a private area where they can satisfy all their filthy needs. Any questions?" "Yes," I said. "Did I see a bedroom connected to this office. And if so, could we retire to it after lunch? I'm feeling like I need a nap. With you. In our lingerie." I seemed to have a natural knack for flirting. Because Brenda forgot all about lunch, except to put a post-it on the door for the food-service person, saying we had changed our minds. She then took me by the garter belt into her office-connected "stabbin' cabin" and flung me onto the bed. It had only been 18 minutes since my last orgasm. And I was 50 years old. But I was stiff as the fine for doing 90 in a school zone. Brenda peeled off her dress. She looked great in her black lingerie and stockings. She even left her big heels on for an extra little dollop of sluttiness. There was obviously no need for panties, so we both shucked them. Oh my. Brenda was stiff too. And it had only been 12 minutes since her cum tsunami. What did they put in the water at Late Vocation? Despite our fierce lust, Brenda set a deliberate pace to our lovemaking. For the first time in my long sex life, I was not the pace setter. All I had to do was do what Ginger Rodgers did with Fred Astaire. Everything Fred did, but backwards and in heels. I loved being the sex object. The submissive one. Yum! Brenda was definitely an alpha. Which is probably why she had the leadership position in the chapter. Or maybe she fucked her way to the top. Either way, I liked Brenda! We tongue-kissed and gently fondled each other's cocks for a good half hour. A very good half hour. Brenda insisted on two breaks to freshen our lipstick. I liked that too. I especially liked when Brenda assaulted my nipples. No one had ever done that. [sigh] Some regret for lost time there. But mostly joy at how delicious it was to have my nips sucked so nicely. With a well-lipsticked mouth. Attached to the very feminine Brenda. Brenda was a very naughty girl about one thing, however. Every time I was about to scream and cream, she backed me away. "Save it for when I fuck you," she breathed the third time she did it. "It will be so awesome to cum while I'm rubbing your prostate with my stiff cock." [Gulp] Brenda was going to FUCK me? In my ass??!?! Taking away my full masculinity? Maybe forever? Well, get on with it, girl, I thought. Fucked. I was going to be fucked. On my first day as a Late Vocation member. I told you I was an overachiever. Brenda locked eyes with me when she announced her intention to fuck me. If they had flickered a no, she would have backed off. But my eyes gave her a big green light. And she began to rev things up. She reached into a nearby nightstand drawer and extracted what looked like a toothpaste box. She opened the box and took out what looked like a slightly curved, smallish banana. It had lots of holes in it and one end had a big loop attached. "This is the new Spermbutt Anal Lubricant applicator package, Honey," Brenda said. "I'll ease it up your sweet pussy and push the discharge button. Your pussy will be filled with a soothing gel that will make our fuck much more pleasurable for us both. OK?" I whimpered my consent. I know by now you think I'm a daredevil. And I mostly am. But getting your keister plowed for the first time is a scary moment for us all. Brenda slid three pillows under my hips. She leaned over and tickled my anus wrinkle. Then gave it a little kiss. Then Brenda sat up and rubbed the lubricated tip all around where she had just kissed. Oh! I was terrified and ferociously aroused. The best combination for real fun. She gave the Spermbutt Anal Lubricant applicator/dildo a little push. Just into my pootie. About an inch. I screamed and shot my load. Thick creamropes. I know. I should have waited. But I couldn't, OK? Brenda didn't seem disappointed. She seemed pleased that I was so responsive to her. Then she shoved the rest of the applicator into my pussy. Ow! Not a huge ow. But, ow. It hurt some. But the pleasure of feeling the first erotic implement of my life on my prostate trumped that a lot. Just for a couple of heartbeats, though, I wondered what it would feel like to have her actual cock inside me. Rubbing my prostate. As we deep tongue kissed. I soon found out. Brenda produced what looked like a half-gallon bottle of Spermbutt Anal Lubricant, slathered it all over her cock, pulled out the applicator and replaced it with her cock. I gasped. It was so big. And hot. And hard. And every push against my prostate felt as if I were entering a new dimension. Twilight Zone stuff. More like the Best-Fuck-of-my-Life Zone. I loved being fucked. More than I had ever liked fucking. I guess it was the notion that I was "giving myself" to my sex partner was what enthralled me the most. I had always been the rutting, snorting, selfish "taker" and now I was the grunting, gasping, squealing, screaming "giver" in the lovemaking. I liked that. I liked that a lot. Was I a true "bottom?" The evidence was mounting. As was what appeared to be an orgasm - deep within me. Which was, of course, impossible. Me being 50. And having cum twice in the past hour. But there "it" was. And "it" was getting stronger by the millisecond. I could feel that "it" was different from any such welcome visitor in my life. "It" was an anal orgasm. And a real corker. Brenda was kissing me with wet tongue and grunting really heavily. Signs of her own impending orgasm. She would be filling me with her hot cream in moments! And I would be marked as a submissive little sissy forever. I decided I would concern myself with all that once I regained our planet's surface - since I had departed same when my analgasm slammed into me! It was wildly different from any of my previous zillion or so orgasms. It was deep. It was astonishingly intense. And there was no hurling of sperm. Merely a steady drizzle of watery ball juice. Whish was what was left, I supposed, after the previous two rounds of the bout. But the drizzle surprised me. I don't always get a drizzle when I'm being ass-fucked these days. But it seems to be coincident with my most stunning cums. Anyway, back to the narrative. Did Brenda fear for my life after I "left it all on the field" like that? Not really. She was clawing her way back to the high ground after being hurled off Cum Cliff. And it was barely even money that she would make it. When Brenda's cock plopped out of my highly grateful asshole, the erotic thing to do would have been to take it into my mouth and pleasure it until Brenda produced another stiffie. But hey. We were in our 50s. And we were biological guys. So when Brenda said, "Nap?" I answered "Nap." Ten seconds later we were asleep spooned in each other's arms. Chapter Four - Looking around At 5:32 p.m., I felt my neck being kissed and my asshole being penetrated by a nice thick cock. Mmmmm. My favorite new way to wake up. And Brenda was my favorite means for such wakeups. Except... It didn't exactly feel like Brenda in my "pussy." And it didn't feel like Brenda's neck kisses either. Not that I was complaining. It still felt lovely. But who... I looked over my right shoulder and saw... Linda! The receptionist who had such a crush on me after I sucked her cock. Should I be angry that Linda somehow insinuated herself into Brenda's office bedroom, despite "do not disturb" signs and what I thought were strong locks? Maybe. But I wasn't. The fuck was just too nice. As was the lovely way Linda was skinning my peeny as she fucked me. It was delicious. So much so that Linda and I were soon cumming as one. In big spurts. Happy spurts. And to think that I had only walked in the door of Late Vocation less than nine hours earlier. Don't you just love America? Land of innovation. Inventors of all the important stuff. Like airplanes. The light bulb. Nuclear weapons. Spermbutt Anal Lubricant. And Late Vocation. Anyway, Linda and I enjoyed a whole bunch of post-coital tongue-kissing before we discussed how that lovely situation had developed. At 4:30, while I was still sleeping, Linda said, Brenda popped up and ran into the bathroom to take a shower. Then Brenda slid out of the bedroom and went to her private transformation room, where she became Wesley again. Complete with khaki pants and cardigan sweater. His grandson was in a school play that evening and he and his wife of many years were not going to miss it. Huh? I asked what must have seemed like the dumbest of rookie questions. "You mean Brenda has a straight life outside of the club? With a wife? Who's a grandma? And he has grandkids' school plays to go to?" Linda looked at me with an expression of amazement. "Of course, she does, Sweetie," Linda said. "We all have 'straight' lives as men outside of the club. We come here to feed the beast within us that urges us to crossdress. And to make love with our fellow crossdressers. Here is fantasy. Great fantasy. But fantasy. Isn't that what you thought when you joined?" I thought about it for at least 60 very quiet seconds, then said, "No, Linda. I don't want to have another life outside these walls. I want this to be my home base for lots of fun times, but I'm never wearing men's clothes again. I'm all in." That truly amazed Linda. Not to mention me. I meant it all, though. Linda responded after a decent pause. "Then that's what we'll help you do, you brave pioneer, you. Brenda asked me to take care of your needs tonight, show you around and introduce you around. But you have a long-term goal, so we'll make sure you're ready for that. I'm off from work today and tomorrow. And I'm single. How about if we go shopping right now for what you'll need, then we'll take it to your place and organize it? Then we can come back here tomorrow sometime and I'll show you around?" That sounded great to me, so I said so. Following Linda's lead (I was a bottom after all), I showered with her (and she wanked me to a limp-dicked cum). Then we dressed up from Brenda's collection of stockings, garter belts and nighties. I went pink and Linda went black. We slid on our heels and made our way through the connected hallway to Late Vocation's sister store, T-Woman. Where the mature pantyboy can find whatever she needs to become delicious. According to their ads anyway. A very pretty younger pantyboy led us through oceans of panties; a forest of seamed, fully-fashioned, reinforced-heel-and-toe stockings; and tons of garter belts, nighties, camisoles, teddies, stiletto- heeled shoes, and even dresses and skirts to wear in public. I also secured a year's supply of cosmetics and [blush] Spermbutt Anal Lubricant. Thousands of dollars later, Linda assured me that if I gave the salesgirl my house key and address, her staff would not only deliver everything, but would set it all up in my bedroom, carry away all my male clothes and paraphernalia, and be waiting there with the key to let me in. "Just give us 90 minutes, Miss Colleen," the salesgirl said. Hmm. I LIKED being called "Miss Colleen." But what could Linda and I do for 90 minutes? Linda, the little scamp, knew. "Let's eat," she said. "I haven't eaten since this morning and neither have you." Good idea, my stomach replied, So we wore loaner raincoats from T-Woman over our lingerie, got into my car and went through a drive-through window for fast food. Linda drove, since I hadn't yet gotten the hang of driving in spiked heels. And I wasn't sure I wanted to deal with the conversation I would need to have with the burly, hairy, manly policeman who would stop two lingeried sissies. Although a part of that was very exciting to me. Even then. We sat in the car and ate and chatted for 90 minutes. During which time it became clear that Linda was a definite top who couldn't wait to top me again. Linda learned that I was more than OK with that. We arrived at my 2,000-square-foot, upgraded and renovated, three bedroom condo at the precise hour our T-Woman salesgirl directed. And there she was. Handing me the key and showing me my newly- femme- equipped master bedroom. It was a dream come true. Even though I had only had that dream for about a week. Didn't want to offend the salesgirl, but I hustled her out. A $500 tip richer. Linda and I had serious business. I liked Linda a lot. And she looked so darned sexy in that black lingerie and stockings. Neither of my wives would have worn stockings and garters to bed. And never a babydoll like Linda was wearing. I couldn't help looking in the new, full-length mirror that T-Woman had thoughtfully added to my room. Pink stockings. Pink heels. Pink garters. No panties. And a lovely, see-through, pink, shortie nightie. I didn't look half-bad for an old broad. Who happened to be a former guy. Could I "pass" for a woman in the big world? At that moment, I considered that question a bridge too far. I had lots of other water to navigate. I tore myself from my reflection and saw what most pantyboys (or [gasp] men) would find delicious. Linda was lying on her back on the bed. She had removed her spiked heels, and her panties. Her yummy prick was stiff and exposed. The head was resting enticingly on the hem of her black, lacy babydoll. I had to have it. I kicked my shoes off and got into bed with Linda. We kissed and fondled each other's cocks for a lovely 15 minutes. Things were getting a bit too hot for further foreplay. I wanted to suck Linda's cock and swallow her cum. But I also wanted her to fuck me. Hmmm. Linda seemed to be awaiting my decision. I made it. "I want you to fuck me, Sweetie," I said to my new and dear friend. Another advantage of pantyboys over women. Much less ambiguity. As if my education hadn't advanced enough during that glorious first 24 hours as a pantyboy, I got a PhD lesson from Linda. She didn't rely on just that new-fangled Spermbutt Anal Lubricant stuff to get me ready for what every pantyboy wants - a good, stiff fucking. No. She "prepped butts" the old-fashioned way. With her tongue! Right in my pink wrinkle!! As deeply as she could worm it in!!! It was almost as good as the fucking that followed. Linda ate her dessert for 23 minutes. During which I think I screamed loud enough to open graves in the next county. And creamed as if I hadn't spunked in a week. Bowing slightly to modernity, Linda did slather a nice portion of Spermbutt Anal Lubricant onto her aching, red-as-fire prick just before she impaled me. Oh, girls! We all know how that feels, don't we? It's the best stuffing there is. Well. We slept the sleep of the innocent after that, Until I woke up to tinkle at 3:14 a.m., returned at bed and decided that I wanted a bit more of Linda's wonderful spunk. She was delighted to nourish my ravenous mouth and throat with her sissy cream. Awake for good at 7:35, I faced reality for what I hoped would be one of the last times. Linda needed a shave. I needed a shave. We didn't look quite as "passable" as we had the previous evening. But so what? I sucked Linda's cock to get it nice and hard, then sat on it and rode it to a lovely double-spunking. Somehow we managed to get ourselves fed and in girlish order by 10:12. I loaned Linda one of my dresses - a lilac sundress that she wore with tan stockings and lilac heels. I wore a yellow minidress that showed off my brown-stockinged legs and yellow stiletto pumps. We both wore blond wigs and lots of make-up. Not bad. Especially since it would be my first opportunity to meet my fellow club members. And, as it turned out, someone else. It was broad daylight when we left the house and all broads can be seen clearly in daylight. So I wasn't surprised on the way to my car, that Linda and I ran into my 70-something neighbor, Mr. Riley. He was startled to see us for two reasons. First, he told me later that we were the most feminine creatures he had seen in 25 years. Second, he recognized me as his former male neighbor. "Is that you, Connor?" the nice, but bewildered man asked. "It's Colleen now, Mr. Riley. I'm dressing and living as a female full-time now." Not a sentence one hears every day. So it took a moment for Mr. Riley to process it all. Then he said, "Well, from the looks of it, Colleen, you're awfully good at it. You're a babe! And so's your friend." He asked Linda, "Are you a man dressing as a woman too?" Linda was pleased with the question. Since Mr. Riley was unsure and "passability" always seems to be on many transgendered people's minds. Frankly, my dear, I don't give a damn if someone says to his or her companion, "Isn't that a man dressing as a woman?" I dress to meet my needs. Not for others. "Thank you, Mr. Riley," I said. "You've always been my favorite neighbor. And your tolerant response to my new life has earned you an on-my-knees, full-swallow blowjob at a time and place of your choosing." The older man's face flushed at that. Then he said, "How about now, Honey? The wife is at her volunteer work until 5 p.m. I would be delighted to have you swallow my cum. And I would love to show my appreciation by sucking off you and your pretty friend. " I looked at Linda. She nodded assent. How could we refuse such a kind offer? Linda and I entered the Riley apartment., which had last been renovated when Fred Flintstone was in high school. Linda sat on the Rileys' couch while I got to my knees and serviced Mr. Riley's very nice cock. It was long and thin. And it had been a while since it had been exercised. But I made up for that. He wasn't hard at first, but a stockinged pantyboy on her knees licking and kissing one's knob tends to be a good remedy. Mr. Riley was hard in two minutes and cumming down my throat seven minutes later. He seemed OK with that, just as he seemed OK with most things. Surprisingly, I was OK sucking Mr. Riley's cock and swallowing his tasty cum. Considering that Mr. Riley was a MAN! Did you notice that or was it just me? Mr. Riley was a man and to that point, I had only been with pantyboys. And only two of those - Brenda and Linda. Less than 30 hours after my pantyboyhood had begun, I was laying down a really nice pattern of sluttiness. I think that If Linda hadn't been with me, I would have sucked Mr. Riley to a second stand and let him fuck me. But Linda was waiting for the BJ Mr. Riley had promised her. And she got it. As did I. Mr. Riley was an exceptionally great cocksucker and his fingers knew just where a pantyboy's prostate was. And what to do with said prostate once it was digitally located. I guess I should ask him about all that someday, but Linda and I were eager to get to the club. We gave Mr. Riley the kisses he had earned and we made solid half- promises when he told us which days his wife was out of the house. Linda insisted that I drive that time, despite the fact that I was wearing a pair of 3.5-inch stilettos. "You'll need to learn soon if you're serious about going all full-time on the world," she said. Good point. Chapter Five - Tiffany We avoided death and arrived at the club in time to change before we grabbed a late lunch in the club cafeteria. I was wearing my brown stockings, white garter belt, yellow heels, white bikini panties and a lacy white bra. As Brenda had promised, the food was great. As was the attention I was getting from surrounding tables as Linda and I ate our kale power salads. "I'm going to take you to the gathering room in a minute," Linda said, "But first I need to check something." Linda pulled out her phone, checked an app, and smiled. "She's in the room. Good. She'll be perfect for you." Huh? I asked for clarification. And didn't get it. Instead, I was hustled from the cafeteria to the gathering room - a big place with lots of couches, dispensers of Spermbutt Anal Lubricant and kneeling pads. Not difficult to figure out what went on in there. There were seven or eight members when Linda and I entered. It was a workday and lots of members were out dressed as guys earning a living for their wives -ick!3 Two of the members were quite a bit older than I - maybe early seventies. But they were magnificently turned out in their sissy gear, wigs and makeup. The blonde was on her knees giving the standing brunette's cock an excellent seeing -to. And the brunette was very appreciative. The other members were in a cluster chatting with someone who was the center of attention. As I moved to where I could get a clear view, I could see why attention was focused on the member all in pink - seamed, fully-fashioned, reinforced-heel-and-toe stockings, of course; strappy sandals with five-inch heels; a lacy bra; and a lovely, ruffled garter belt. No panties! Probably because no panties could contain what my eyes beheld. It was a MAN-sized cock on someone whose mannerisms and facial beauty marked her as a paragon of femininity. Her shoulders were a bit broad, but hey, nobody's perfect. That cock. It was a good eight inches. And it was fast asleep! And it was thick! What if it were roused from its den? A pantyboy would be INSANE to try and take that demonic dick into her tiny bumhole. Maybe she was a bottom. Yeah. That's it. But [sigh] that would mean that she and I would never get beyond kiss, tickle and suck. And despite the lethal looks of her weapon, I wanted it! Linda saw my mesmerization and leaned over to whisper, "Her name is Tiffany. And she's a top. A VERY popular top." Gulp. "Go for it," Linda said. Gulp. I froze. But Tiffany thawed me. She caught my eye and stopped chatting with her surrounding sycophants. Who couldn't even excite her enough to make her get hard. She held my gaze and began to walk toward me. Oh no! Be careful what you wish for. I was going to be split in two! Oh no! Linda leaned over and said, "I'll call you tonight. Have fun." And she was gone. I could have gone with her. Rejected the cheap thrill of being fucked by a big-dicked pantyboy princess. Run away? No effing way, OK? I was all in on that pantyboy thing. My executioner stood next to me. In those 5-inch heels, she was about 6 foot 3 inches. Our eyes and cocks were even. "Hi, I'm Tiffany," my imminent defiler said. I looked down shyly before replying and saw that Tiffany was HARD! Completely hard. For me. Not that other bunch she was just consorting with. Wow. I felt special. I choked out a "My name is Colleen. I just joined yesterday. I just turned 50. And I'm a bottom." Oh no. Too much information. Tiffany would think that I was a dolt. But no. She giggled. Sweetly. And femininely. My heart melted. I made the first move. "Uh, would you like us to get one of those suites for an hour or two? Or the rest of our lives? I would really like to get to know you." Tiffany made the slightest show of reluctance, then said, "That would be amazing, Honey. You're the prettiest bottom we've ever had here. And probably the best in bed." I blushed furiously. And thought that I was facing big expectations once Tiffany and I got into the sack. But I was up for the challenge. Tiffany took my hand and led me past the gaggle of the rejected and led me to Suite Three. Tiffany went in first. I stepped in and closed the door. Alone. With a pantyboy top who sported a ten-inch, ultra-thick cock. And a firm intention to inflict it on my tiny, inexperienced bumhole. I couldn't have been happier. So I quickly shimmied down my panties. And unhooked my bra. "You have a beautiful face. And lovely nipples, Sweetie," Tiffany said. "And a beautiful cock. May I make love to you now?" "Oh, please," I whimpered most unmanfully. Tiffany took my hand and led me to the Supreme-Leader-sized bed. Oh. I was lying on my back. My defiler standing above me. Contemplating her game plan to satisfy all of her disgusting needs. And a bunch of mine as well, I hoped. Or maybe she was just admiring my beauty. Which was probably the most satisfying thing thus far during my long, almost 40-hour trek to womanhood. I LOVED being lusted after. That had never happened to me as a man. Not as far as I knew, anyway. And here I was being lusted after almost hourly. Not even counting Mr. Riley. Oh. And then there were the orgasms. Best ever. And most frequent. Including the one that was building in my nutbag as Tiffany licked and sucked my "titties." It was off the charts erotic to me. I especially liked the feel of Tiffany's lipticked lips as she assaulted my nips. "I, uh." I grunted to Tiffany and she stopped nipple-diving. Darn it! But Tiffany was wise. She knew that the complete sentence I was struggling to utter was, "I, uh, cum, now." And Tiffany was not allowing that. Yet. "We're wasting nothing today, Colleen," my assertive pantymeister said. And she took my purple cockhead into her mouth and sucked it most deliciously. MOST deliciously. So deliciously that I soon had my hips up and was making sissy squeals as Tiffany gulped down seven thick globs of my cum! Oh! And that was just the foreplay. Tiffany knew her foreplay. And its victims. She switched her oral attentions to their third target, my tiny asshole. Which I was very tartily wiggling at her as I scampered to my stockinged knees. I knew for sure that Tiffany would never be able to force that baseball bat-sized cock into my pretty wrinkle. But I wanted her to eat me out regardless. After that yummy session, I would be happy to allow Tiffany to rub her peelips onto my anus or something. And I would love to lick her knob for an hour or so. But fucking was clearly out. And then it wasn't. Tiffany had me squealing and squirting hard after 27 ass-consuming minutes. And then, with my defenses down, she SHOVED her cock into me!! Yow! That hurt. I wriggled. And sobbed. Trying to expel the unwelcome invader. But then... It wasn't unwelcome any more. It was VERY welcome. Tiffany knew how to fuck a sissy. And I was and am very much a sissy. Who loves being fucked. My bumhole stretched to accommodate her large friend and each push and pull dazzled my aching prostate. I think I had three dry-but-debilitating prostate orgasms during that 34-minute, historic fuck. Tiffany's orgasm, when it arrived, almost sent her to the emergency room. And a very torrid, 15-day, sissy love affair began. Chapter Six - Three Months Later Tiffany and I almost destroyed each other during our affair. The sex was magnificent. But we were becoming too possessive of each other. Tiffany resented whenever Brenda or Linda gave me a bit of the old i- and-out. But what was I supposed to do when Tiffany was home as Kevin with his wife and kids? Or at work? I needed cock, didn't I? I, of course, resented that Tiffany would ever leave my bed to go be that Kevin person. Why didn't Tiffany just give up Kevin, leave her wife and kids and run off with me? Wasn't that what she promised me after all our fucks during those 15 days? Anyway, we parted amicably and I became the club slut. Sampling as many of the members as I could. Until about three months in, when I began to tire of being fed and decided to hunt. At the club, getting laid was a sure thing. Which is fantastic, right? But I wanted to see what else the world could offer beyond sweet, delightful, sex-hungry, beautifully-lingeried pantyboys. So one day, I got out of bed - alone - showered, shaved all over, powdered and perfumed, did my growing hair and got dressed. In a nice, semi-tight and very short minidress. Over black seamed, fully-fashioned, reinforced-heel-and-toe stockings and big heels. I decided to make an expedition to the real world and see what that brought me. Not having bought groceries in three months, I decided to start there. So I drove to my local Savalot Mart, parked, got out and wiggled into the store. Stares. Lots of them. Were the stares of the "Look at that sick tranny trying to pass" type? Or were they the "Oh! What a hot piece of ass!" type? I didn't know and mostly didn't care. I had become quite comfortable as Colleen and anyone who wasn't comfortable with that could go pound sand. My shopping basket was half full when someone bumped his basket into mine. Perhaps not by accident. "Oh," the clumsy cart-driver said. "I'm so sorry, miss. I was just so startled by your beauty that I wasn't aware of where I was going." I'm happy to report that I was still able to blush at such an obvious pick-up line, And such a handsome picker-upper! He was tall and in fine shape. He appeared to be in his mid-thirties, which would make him young enough to be my ...younger brother. Though I was new at flirting, I knew that the best way to acknowledge his "beauty" comment was to merely bat my eyelashes shyly. Being shy also has the advantage of allowing one to look down and check out bulges. His looked very nice! Oh dear! Did he see my bulge as well? No matter. I wasn't shy or ashamed of my pantyboyhood. My almost new friend continued. "I certainly hope that a big, strong man is meeting you to help you carry in all those groceries. There's just too many for a delicate flower like you." Did he really think I was a delicate flower? Maybe he just wanted to get my panties down. No. I was going with that flower thing. I spoke at last. "I see your point, sir. Unfortunately, I live alone. I just don't know what I'll do." "Pardon me for being so bold, Miss, but I would be happy to assist you in any way you see fit." I paused for effect. And to show I wasn't a complete slut. But then I showed I was. "That would be so kind, young man. Thank you. What's your name?" The man flashed a big smile. "I'm Matt. And you, pretty lady?" Oh no. I blushed again. It was true. I wanted Matt's cock up my bum and I was doing all the slutty things to get it up there. "My name is Colleen." "Well, Colleen, shall we finish our shopping, load our groceries, then I'll follow you home to help you?" I agreed and that was what we did. Matt hauled my stuff in, helped me stow it away, and stood there, seemingly enjoying my discomfort. Until... "If you're nervous that I'll be a big jerk - maybe even a dangerous thug - when I discover what's between your legs, please relax. I saw you as you are the moment you came into view. "You're a lovely, ultra-feminine person with great fashion sense, a terrific spirit of adventure, and a nice bulge in your panties." Oh my. Matt UNDERSTOOD me! Which is the greatest aphrodisiac of them all. I stepped forward, folded into his arms and let him kiss me. With tongue. As he slid his hand under my tiny skirt and rubbed my bum cheeks. After five or so heated moments of that, I improvised. I bent myself over one of my kitchen chairs, lifted my skirts, pulled down my panties to mid-thigh and, tottering on my big heels, wiggled my bum at Matt. Matt took a respectful 20 seconds to react. His voice was trembling as he said, "The sight of your perfect bottom, framed by those garter straps and the welts on your stockings - oh! And the sight of your pink ballbag peeking between your thighs. It's the prettiest thing I've ever seen." My eyes filled up with girlie tears. I was about to be ravaged by a man. For the first time. And I couldn't wait. I loved that he was in charge of my ravagement. No pressure on me. Just fun. But I did make one little suggestion. "There's a bottle of Spermbutt Anal Lubricant in the family room, Matt." He smiled. "We may not need that, Honey," Matt said. And he pulled up another kitchen chair, sat behind me, and showed me how a real man gets his woman ready for an ass-fucking. He ate me out!!! Matt was almost as good at analingus as Linda was. And I imagined that with practice he would get that much better. A big plus over Linda's technique was that Matt skinned my tender knob as his tongue excavated my bumhole. A BIG plus! Matt had me in a major dither about ten minutes into the delightful proceedings. And, of course, I gave a clear, unambiguous testimony to Matt's lovemaking skills thus far. In six thick globs. I was a bit withered when Matt entered me soon after. His cock was a little above average, so after 15 days of Tiffany, it entered me easily. Though I hoped not too easily. Didn't want to give a slutty impression. Yet. Matt kissed my neck and praised my beauty until things got too hot for such discussions. Matt unloaded big-time in my bum. The first manload it had experienced. It was superb. My asshole, it appears, was made for receiving manloads. After its wiggling enticed men to deposit those loads. I'm not sure how Matt and I ended up on my bed. Him naked. Me down to my stockings and garters. But there we stayed, with few breaks, for the next six hours. We fucked often. I sucked his fat cock, of course. And he sucked mine! Which boded well for all my future "hunting" ventures. When Matt left that day to go home to his wife and kids, we made a date for another adulterous time of joy the following Thursday. Was I too bold, you say? Did I accept full-time pantyboyhood in no time flat? Instead of sneaking and hiding and leading a double life? One life is enough for me, thanks. And a late vocation is better than no vocation. 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