Ante Up

urtles53 - 20/11/2025

I was turning forty in a few days and feeling a little down. I think all birthdays that introduce one to a new decade have that effect, but forty has always been the cliched one you hear about. It makes sense too, as it has become the official marker of being middle-aged. That is if you are lucky enough to reach eighty and beyond! I had not set the world afire, but I never had much ambition or direction really. I pretty much just drifted and partied through life up till then. I had already been married and divorced twice, and being a good husband was not in my skill set. I had actually fallen into a pretty good gig by my middle thirties as a geriatric CNA working private duty for a very high-end clientele in Florida. It could be challenging work, but easier than hard manual labor. Much of the time you were just a pleasant and understanding companion. I did have one kink I kept under wraps through two marriages and life until my late thirties. I was a secret crossdresser. No one ever saw me doing it and I never got too fancy with it. I would also imagine I was the woman when I was having sex. I didn’t really feel gay or enjoy gay porn, I just wanted to be the woman in sexual situations. That opportunity arose when I met Bob. Bob was a very successful retired businessman in his early sixties whose wife has been stricken with early onset Alzheimer’s. My reputation as a CNA who did well with female dementia patients had spread throughout the very high-end retirement community Bob and his wife lived in. I soon found myself caring for his wife while earning a very healthy paycheck. Bob and I instantly hit it off. As is so often the case, the spouse of a dementia patient often has no one to talk too and they become isolated. I learned early on a huge part of my job was providing companionship to the caregiving spouse too, and Bob made that very easy to do, as I truly liked him. We were opposite in every way, and I believe that was part of our attraction to each other. One afternoon Bob and I were in a deep conversation, and confessions were being exposed right and left. He brought up how much he missed having sex with his wife. One thing led to another, and we ended up in bed together for a very nice afternoon of sensual pleasure. I told him about my crossdressing, and he became quite excited about that kink in my persona. We became lovers and he supported my crossdressing emotionally and financially with outfits, wigs, make-up, even electrolysis! Bob used to joke that he built his very own sexy bitch from scratch! I was very slim, petite, and had feminine facial features as it was, so I ended up looking very sexy if I have to say so myself! I would care for Bob’s wife first thing, then spend the rest of my shift in bed with Bob. He was one blue-pilled fueled insatiable old dude with a big, tasty cock to boot! Bob and I were both new to this and learned as we played, and the classes were extra fun! After a couple of years, I got very good at being a woman in bed, even without any anal component to our sex. For some reason anal sexual activity did not appeal to me or Bob. We both found many other ways to pleasure each other without going up the poop shoot! Cock sucking, jacking, kissing, rubbing against each other in many positions and ways. It always ended with me nestled against Bob’s manly chest with a gentle smile on my face and often a little cum too! One time Bob asked how I would feel about being ‘gang banged’ by him and a some of his friends. He played poker with a few guys and one of their constant complaints was how they missed sex, by being either widowed or having wives no longer interested in fucking. Bob found the idea exciting, and I had to admit I did too! Bob assured me he had not broached the subject with the guys, as he wanted to fly it by me first. I said the idea did excite me as long as everybody was on board with anal being off the table. I gave Bob permission to run it by his poker buddies and see what shook out. Two of his buddies were very interested in having sex with me, which made it a threesome. Bob sent me photos of the other two guys, and they were very handsome, in excellent shape, and both were in their early 60’s like Bob. One was a widower, and the other had a wife no longer interested in sex. Bob had sent them a photo of me too decked out as “Hedy’”, my female persona’s name. It was me lying in bed dressed in only skimpy lacey lingerie with a flirtatious smile. He said they enjoyed that image very much and were ready to bed me down! We set a date for a week away, ironically on my fortieth birthday, as I wanted to prepare and make it a perfect experience for everyone. I was giddy with anticipation like a schoolgirl preparing for her first prom! I was very smooth to begin with, and the electrolysis made me look like a teenage girl. Bob was smooth naturally and he said his buddies were too, so I wanted to be super tactile for their roaming hands! I had shaved all my pubic hair off too and was hairless except for my wigs. I decided to wear my favorite long-haired wig and some sexy lacey lingerie for my big night. I also found a bra from an online crossdressing supply place that had very subtle built in breasts that looked perfect for the foreplay part of sex. I was a make-up pro by this point and knew how to put on the war paint! I did several dress rehearsals in front of the mirror to make sure I was perfect for the boys. I have to say I looked ravishing and even gave myself an erection! The big day finally arrived! I went to Bob’s early, so I had time to really dress up pretty. I put on the bra, lacey panties, and a beautiful blue satin robe that Bob had just bought me. It was short and went down to just the top of my thighs. I wanted to be easy to disrobe in case these guys were a little nervous. Sometimes I would put on thigh high stockings and a garter belt for Bob, but my legs were super tan and looked nice bare against the cobalt blue robe. My last wife was always jealous of my shapely legs! I put on the long-haired wig I always liked and really put in some time for my make-up. I sauntered into the living room and Bob let out a wolf whistle! “Wowie, you really did it up nice!” he purred, “I think we are going to have an amazing afternoon once Adam and Carl get a look at you!” I sat down on the big couch just as the doorbell rang. It was showtime! Bob answered the door and in walked Adam and Carl, looking every bit as handsome and distinguished as in the photos. I could sense they were a little bit nervous. Bob told me they both claimed to never having had gay sex before. The crossdressing aspect sealed the deal for them. We had never met so they had no previous image of me as a man. I think that was very important. That generation and class of men would feel more comfortable with someone they can look at as a chick rather than another man. I had planned on playing it very demure until I could feel their vibe. I was even a little nervous, as I was about to have sex with three men! Not even many biological women have had that experience! “Gentlemen, I would like to introduce you to Hedy, our hostess for this evening” Bob said with aplomb, “I can assure you we are all going to have a very nice time as we get a chance to know each other better, and I mean way better! We all chuckled at that quip! “Wow, Hedy, I must say you look ravishing.” Adam said with a grin, “Bob gave you high marks, but you have even succeeded my wildest dreams of what you might look like.” “Why thank you so very much, Adam, I do put some serious effort into creating Hedy.” I said softly, “Bob has certainly enjoyed her! Now it’s you and Carl’s turn!” I had practiced a female voice for a long time and got pretty good at it. I had a naturally high voice as it was, and that helped. I also liked to softly moan during sex. That turned me on, not to mention Bob. “Gentlemen, please feel at home and sit down on either side of Hedy on the couch.” Bob announced, “I will sit here in this chair for a while. It will be a rare opportunity and treat to be a voyeur!” I patted the couch on either side of me and smiled as the boys set down. Then I put my hand on each of their knees’. I could tell Carl was more nervous than Adam was, so I decided to start with Adam and let Carl catch up. Adam then put his hand on my bare knee, and I turned my head towards him for our first kiss. It was a nice kiss too, and I complimented him on it. I then turned my head towards Carl when I felt his hand on my bare thigh. These boys were horny for sure! “Oh, I haven’t forgotten you, Carl” I purred sexily, “Give mommy a big kiss.” I continued to kiss Adam and Carl alternatively and any awkwardness or shyness quickly melted away in our passion. The kisses got longer and deeper as their hands moved up my now spread thighs and were feeling my cock/clit through my lacey panties. My hands traveled to each of their crotches and was pleased to feel two nice pieces of swollen man meat ready to be serviced! I moaned and that seemed to excite them even more. I could also see Bob watching us from his chair while playing with his own cock. This was the first time I ever had been observed while having sex and I liked it! Now I could add I was an exhibitionist to my list of sexual kinks! It was like being the star of my own porn movie! By now Carl was the aggressor and grabbed both my legs and dragged me lengthwise on the couch as I let out a little squeal. This landed the back of my head in Adam’s lap and against his rock-hard cock. This was the Viagra posse! Carl opened my robe and ripped off my panties as my stiff cock/clit slapped against my belly and he spread my legs. On the other end Adam dropped his shorts and put his very nice, firm cock in front of my face, and it instantly went into my eager mouth! “I have never done this before and hope I do it right”, Carl said as he took my cock into his mouth on the other end. He definitely was doing it right! I was moaning in ecstasy as I was getting worked on both ends. This was heaven! After a bit they switched me around and pulled me up on my knees doggie style. Adam placed his cock along my upper butt crack where he could get some good traction and started fucking me, while Carl got on his knees and fucked my mouth. All three of us were moaning up a storm! Carl then got up and grabbed my hips and flipped me into a missionary position on the couch before he pulled my legs forward so my butt would be on the edge of the cushion. He spread my legs and placed his cock to the side of my mine and against my belly for traction and started pumping. I later learned Bob had given them both pointers on this position, and I instinctively responded. I wrapped my legs tightly around Carl and let him pound me silly, as that friction worked for both of us. In the meantime, Adam stuffed his cock in my mouth and held my head as he fucked my face. We all came at once in a shuddering climax, with Carl and me shooting cum all over my belly, and Adam unloading a huge load of baby batter in my mouth and all over my face! Beings we all came at once there was a silence right afterward that was so serene. Carl left for the bathroom and came back with a warm washcloth and gently and lovingly wiped all the cum from my face and body. Then Carl and Adam both started kissing and holding me tenderly, which was unexpected somehow, but very nice and appreciated. They had both been moved by that experience, as neither one had made love in a very long time. They also both expressed their deep gratitude before they put on their clothes and left me and Bob. “That was beautiful to behold, Hedy.” Bob said softly as he picked me up in his arms, “But you aren’t through yet. It’s my turn now.” Bob carried me to his bed and we made love, the best love we have ever made. I realized how good it felt to provide sexual intimacy for these men in their autumn years. I was blessed to be able to do it. It was my best birthday yet.