So this is continuing my wild night in New York from Part 4 of my story.....
This part of the story is on the transgender side for the reasons you will find out....
After my three-way with Darren and Tristan, I went up to my room feeling a bit dejected and disappointed. My feelings were all over the place after the three-way I had with him, mostly because of Darren giving a bit more attention to Tristan than myself. I could have stayed for another round with them, but my feelings said otherwise.
When I got up to my room, and here I was stuck with a case of blue balls, because I didn't orgasm from the three-way I had with them. I don't know why I did what I did next, but maybe it was because I was feeling dejected and spiteful. I pulled up my phone and decided to text Mia, the girl I had met at the club that was dancing with the transgender female, Alana. It was a simple question of "You up?" After all, it was around 2am in the morning when I got back to my room. Surprisingly, I received a text message back, saying a hello to the special guy with the special friend.
It was then we got texting back and forth, which started off tame, but became more so in a flirtatious and sexual manner. I then shared that I didn't have so much fun with my three-way with my "special friend", and didn't get satisfied from the experience. It was then I received a text back stating that she could maybe help with that, if I was "up for it". Of course my horny alarms went off, and I couldn't resist, given I was suffering from a case of blue balls.
I suggested that she come over to the hotel. She stated that she could be over in less than ten minutes, given she lived nearby. I told her to give me fifteen, so I could freshen up. I hopped into the shower quickly, washed all my crevices and gave my teeth a good brushing after taking in some loads into my mouth. I sprayed on cologne, and changed into a nice pair of black pyjama pants and a t-shirt.
Soon I heard a knock on the door. When I opened the door, it was to my surprise that it was instead Alana. When I greeted her, I was surprised and asked where Mia was? It was then that she stated that Mia was at home. I then went over in my mind whether the number Mia gave me was instead Alana's. I asked her about this and whether Mia catfished me at the club. Alana stated that it was indeed Mia's phone number she gave me. I then asked whether Mia instead stated that Alana should show up instead of her. Alana would then finally come clean, stating that Mia had gone to bed and that her phone was left on the kitchen counter. Alana was still up and heard the texts and decided to answer them, knowing it was myself. I was still skeptical of the whole situation, asking jokingly if this was a test or something. Alana giggled, stating that maybe it is depending on what else happens tonight. She then asked if I was going to let her in, given she was still standing by the front door. I obliged her, letting her in.
She walked into my room. Alana was wearing a long winter coat, with heeled boots, which I imagined were the long fashionable winter boots. She sat against the desk in my room, while I decided to take a seat on the bed. She asked if I had anything to drink. I offered a cooler that I had bought at a liquor store a day ago that I still had. She accepted, and I pulled it out of my fridge, opening it and handing it to her.
I then stated to her that this was all a surprise and I didn't expect to see her here. She laughed, saying that the city is full of surprises, especially at night. I then asked if her and Mia were a thing. She stated that they are roomies, but have had some fun on occasion when Mia's vibrator or dildo isn't doing it for her. We both laughed at this. Alana then asked if me and my "special friend" were a thing. I told her that we had a beneficial relationship. I even shared that it was him that made me bisexual, as I was previously straight before. She acknowledged this, stating that usually the daddy figures are the ones who will break the younger straight guys.
I asked about when she transitioned. She was pretty open about it, stating that it started out in her early teens, and as she moved into her twenties, she committed to fully moving forward and eventually looking to save up for further enhancements and surgeries. I respected her for the commitment, telling her that if it wasn't her voice and noticeable apple, I would think she was a hot little blonde. She giggled and thanked me for this.
Alana then took a last swig of the cooler I gave her, and then stared at me with a smile and gave me the "Sooooo!" expression. I shook my head and chuckled. I was a bit shy of the whole situation. She then asked me if I was ever with a transexual before. I told her it would be my first time. She giggled, stating that it's the best of both worlds. I nodded and smiled.
Alana then asked me "what I was waiting for", saying it was almost Christmas, and I didn't want to open a gift early. I took that as my cue to come over to her. I got up from the bed and walked over to her. I unbuttoned and opened up her long winter coat. Alana once again surprised me, as when I opened up the coat, underneath she was wearing black lingerie. She had thigh-high black boots on, with a garter belt. She had her belly button pierced, and had a small angel wing and devil horn tattoo on her shoulder. I still remember my expression, being a "whoa". I could see her package underneath the black laced panties she wore. I would say she was probably between a B to C cup for her breasts. I could see her bright pink nipples through her bra. I held her hips with my hands, as we embraced close. I brushed against her face. Alana giggled, asking if I liked what I saw. I stated yes indeed. I was a bit more forward and confident with Alana. I brushed my lips against hers, before going in for a kiss. Instantly our tongues touched, and we started to kiss each other deeply. I pulled off her coat, dropping it to the floor. Our bodies touched, and I became hard quickly. I began to kiss on Alana's neck. I heard her breathe deeply. She grabbed my ass and grinded her cock against the tentpole coming through my pyjama pants. I kissed her shoulder, slipping down a bra strap. I pulled down half of her bra, exposing her breast and her bright pink nipples. I kissed and sucked on her breast and nipple. Her breathing turned to moaning.
I felt Alana's hand reach down to my pants. I felt the waistband of my pants stretch out, as her hand went for my cock. She began to stroke me. I reciprocated and rubbed my hand against the outside of her panties. I felt her hard-on. Surprisingly, she had a fairly large cock for a petite transexual woman. I pulled her panties to the side, exposing her cock. I stroked it as I kissed her again deeply. Soon I felt my pants being pulled down and my cock exposed. We both moaned underneath our kiss as our cocks touched one another.
Alana then told me to get on the bed. I followed her lead, laying back on the bed. I took my shirt off, as she pulled down my pyjama pants, getting me fully naked. She got onto her knees on the bed in front of my cock, as she began to lick up and down my shaft. Her tongue was exquisite, as she teased around the head of my cock before going down on me. I moaned as Alana began to suck me off. I guided her up and down my cock. She moaned as she went to town on me, stroking me and sucking me off. This went on for a good few minutes, before I told her that I wanted to return the favour to her.
Alana giggled, and stated "absolutely honey", as she knelt fully up, pulling her panties to the side. I got onto my knees in front of her, licking the pink round head of her cut cock, before fully engulfing my mouth around it and began to suck her off. Alana gasped and moaned from the pleasure I was giving to her. She guided my head up and down, fucking my mouth. I moaned to let her know I was enjoying it. I heard a few times saying "that's it baby". She was certainly enjoying it.
She then stopped me, telling me that she wants me to get her pussy "wet". I knew what she was wanting, telling her to lay on her back. I slid off her panties and raised her legs in the air. I told her to hold them back. I got in front of her, prying her tight little buttcheeks open. I exposed her little pink hole. I slid my tongue down from her taint, before tonguing and teasing her hole with. She gasped and moaned. I heard her say "yes baby". I then went to town on it, tonguing her hole deeply, giving her my best efforts at a rim job. Alana moaned in pleasure and I heard a few "oh my god's" under her gasping and breathing. All the while, she stroked her cock while I did this.
Alana finally couldn't take anymore, and stated she wanted my cock in her ass. I obliged her, running to the bathroom and getting some lotion to use as a lubricant. I told her to get into doggystyle position. She followed suit, taking her bra off fully, exposing her beautiful breasts. I rubbed the lotion around her hole, taking in a finger to get it fully lubricated. I rubbed a ton of lotion on my cock, before positioning it against her hole. I held my cock, guiding slowly into her hole before it fully slid in. Alana gasped as this happened. I pulled her upright, giving her a kiss before putting her back down on all fours. I gripped her hips, pumping her slowly before working up the pace. Alana moaned as I fucked her ass. I ran her nipple between my fingers, pinching and pulling at it. Soon, I started pumping her hard and deep. Alana moaned even louder, gasping when I hit her g-spot. I slapped her ass when I went for a deep pump into her.
I instructed her to get on top of me and ride my cock. I sat upright, as Alana got in front of me, facing myself. She guided my cock back into her hole, before riding and grinding me. While she did, she had her hand on her cock, stroking herself as she did this. I went to town on her breasts, sucking and nibbling her nipples. I licked around the areola, before sucking and nibbling on her nipples as a way of teasing her. Alana moaned and gasped. She began to dirty talk, telling me I was fucking her so good.
I was getting to my breaking point and wanted to finish Alana off good. I got her off on top of me, and pulled her down to the edge of the bed. I stood in front of her, raising her legs and butt up in the air. I slid my cock into her hole again, driving deep and fast. Alana moaned louder, saying that I was going to make her cum. I decided to help her out, stroking her cock, while I pumped her. It wasn't long before I felt myself about to cum. I stopped and pulled out, reaching orgasm and shooting my load all over her stomach and breasts. Alana followed suit, coming onto her stomach. We both moaned, and I collapsed next to Alana, laying on the bed.
We took a break, laying next to each other. Alana remarked about the experience, saying that she hadn't been fucked like that for a long time, giggling as she told me this. I told her I was relieved, getting to release out my "pent up" load I had all night in me. We shared a laugh.
I then asked her out of curiosity if the roles were reversed. I think Alana knew what I was talking about but played it off, asking what I meant by the question. I went more subtledly, asking if she was ever the dominant one. She replied by stating she has been with some females and of course with Mia a few times but asked if I was alluding to guys. Alana gave me this evil look after she asked this. I shook my head, chuckling and finally stating yes. Alana said that she has dabbled a few times with some guys "the other way". She then stated that if I was asking she wanted to top me. I was shy about this, but stated I was curious if she had done this. She then stated that if I was topped by my "special friend", it wouldn't be anything new to myself and that I could be forward with her. I mustered up the courage and then said to her that since I gave her a good fucking, maybe she could return the favour, only if she wanted to. Alana gave me a kiss again, saying to go wash myself up and get ready for her.
I rolled off the bed, and hit the shower again quickly, washing my cock and my hole. I shaved a bit of my hair around my hole as well, to make it a bit more clean for her. I exited the shower, wrapping a towel around my waist. I walked into the room again, with Alana waiting on the bed naked with her garter belt and boots on. She raised her eyebrows evilly, telling me to come over.
I walked over to Alana, staring at her. I was already semi-hard underneath my towel. She then said to "let's see the merchandise", slowly unwrapping my towel and dropping it to the floor, getting me completely naked. Alana takes my cock in her hand, stroking my cock and getting me fully hard. She then asks me if her "toy" would like a little pleasure from his master. I grinned at her and nodded my head.
Alana licks again around the head of my cock, teasing me before taking me completely in her mouth. She sucks and strokes my cock, while staring at me in my eyes. It was pretty hot, and I enjoyed it. She then stopped midway, stating that her "toy" needed to show his master some appreciation. I was digging the whole sub vibe she was going with.
Alana stands up in front of me, her cock semi-hard. I get onto my knees in front of her and I stroke her cock to get her hard again. She moans as I do this. I lick around the head of her cock, tasting a bit of residual dried cum on it. I lick up and down her shaft, before engulfing her in my mouth again. She gasps and moans as I begin to suck her off. She cups my head, controlling me. A few times she shoves her cock deep, making me gag a bit.
Alana stops me again, asking if her toy wants more pleasure. I nod my head. She instructs me to get onto the bed and lay down. She gets on top of me into a 69 position. She then tells me that her toy will only receive pleasure if he does as his master does. She starts to suck my cock again, looking back at me. I take my cue, taking her cock and bending down to my mouth. I suck her cock upwards, and we go at each other's cocks in 69. She stops again midway, asking me if her toy is ready for her. I told her yes.
She tells me to turn over and onto all fours. I do as she says. Alana then asks if her toy wants to be prepared for her. I told her yes, not knowing what she had planned. I feel her pry my cheeks apart, before feeling the flick of her tongue against my hole. I gasp from this, the feeling scintillating. She spits and tongues my hole, getting it wet. I moan a few times from this, completely horny and wanting her to take me. She then asks if her toy is now ready for her. I say yes. She tells me to beg for it. I tell her I want her inside me, turning and looking at her.
She goes to the nightstand, grabbing the lotion and putting some against my hole. It's cool and creamy. I watch as she grabs some, rubbing it against her cock. I watch as she positions herself in front of me, prying my cheeks open and exposing my hole. I feel her cock press against it. Soon it slowly slides into me. It finally fully goes in. I gasp as she is inside me. I feel her slowly work her pace up. She grips my cheeks, pumping me. Soon she gets a good pace going. I moan and breathe deeply, gripping the sheets. She smacks my ass, stating what a good toy I was. She tells me not to stroke my cock, as I feel her hand reach around and grip it cock. She strokes me, while pumping me. We both moan even more.
She stops midway, telling me to get on top of her. She lays on her back, as I guide her cock into me, while I face her. I begin to ride her cock, grinding against her. I start to stroke my cock again, but she tells me that her toy is not allowed to stroke his cock. She pinches my nipples as "punishment". She smacks my ass a few more times as I ride her. Alana asks if her toy wants to kiss his master to show his fealty to her. I nod again, bending down and kissing her. Our tongues tangle with others. Her cock slides out of me as we make out, and she flips me over onto my back. She cups her breasts towards my mouth, telling me to suck on them. I suck and nibble on her breasts. Alana moans as I do this. Our cocks grind against others.
Alana then whispers in my ears if her toy wants to be fucked again. I whisper back yes. She asks me to beg again. I told her yes. Alana raises my legs in the air, pushing my butt up. She holds my legs, guiding her cock again into my waiting hole. She slides into me easily. She grins evilly, as she begins to fuck me faster and harder. I moan in pleasure. I again try to stroke my cock, but she tells me no, and that there will be no need for me. She pumps me harder, hitting my g-spot each time. I moan louder, gripping the sheet. My hard-on is flopping against my stomach. Alana begins to moan more now. I feel that we are both almost there. Alana in between her moans and breaths asks what hole her toy wants her cum in. I gasp inside me. She tells me to beg for it. I begin to beg, asking her to cum inside me. Alana tells me she can my pre-cum oozing out. I start to feel that rush that I felt when I was being fucked by Darren. I let out a loud moan, feeling my cock stiffen and finally bursting cum onto my stomach and chest. Alana does a final pump, holding her cock at my g-spot. I feel the pulsing of her cock as she cums deeply into my hole. She lets out a scream, as she reaches orgasm. She must have cummed at least six to seven times inside of me.
Alana slowly pulls her cock out of me. I feel the ooze of cum that slides out of my ass and onto the sheets below. Alana collapses next to me. She smiles and giggles, stating that I think Mia would definitely like me a lot. I'm a bit puzzled by this. I then ask if this was a test of some sorts with her. Alana then admits that it was a test to see if I'd be a good fit in bed for Mia and that I certainly passed those marks. She also remarked that if a "man can please his woman in all sorts of ways", then I would be a good fit for her friend. I shook my head smiling. She then suggested that we should all go do breakfast the next morning so I could get to know Mia a bit better.
I turned to the clock and it read out at 4:30am in the morning. I had to get up early for the drive with Darren, but something told me to skip out on this and hang out with Alana and Mia. At this point I was running on fumes and my mind was all over the place. I suggested that I could have breakfast with them early enough, but that I would have to catch a train from Grand Central to Boston as I had to be at a meeting there for Monday. Alana stated we could go to a place at 9:30. I was frazzled, but I agreed to do so.
I called Alana a cab and walked her down to the lobby, sending her on her way. When I went back up to my room, I was trying to process everything that happened that night. As much as I was disappointed at what happened with Darren, I felt a bit bad about what I did afterwards. I was never a spiteful person. Maybe it was just the emotions of the breakup that rose up again, and I put that on him. I didn't want to hurt his feelings. I didn't want to confront the whole situation that happened that night and have an awkward car ride to Boston.
I looked up and got myself a train ticket to Boston just after 12:00pm. I called down to reception, asking if they could pass a message to Darren's room that I had checked out early and that I didn't need the rental car ride that we were planning out. I knew this was all a lie, but I just didn't have it in me to talk or discuss with him how I had felt tonight.
Early next morning, I checked out of my hotel room and met up with Alana and Mia for breakfast. It was a cool experience. We talked and laughed with each other. Mia did ask me and Alana about the texts on her phone. We all laughed about it, but I stated that I was hoping to get to know her more. I even shared my sexuality with her. It was so open and free talking with her. Alana even added the remarks that I was "UBER GOOD" in bed and that she wouldn't have suggested meeting up for breakfast if it was bad.
Before leaving for Grand Central, Mia said that if I was ever in New York again to hit her. We exchanged emails and I gave both her and Alana a hug before I left. I got to my train on time and I ended up passing out from exhaustion the night before. When I got to Boston and checked into my hotel, I got an email from Darren saying he heard I had checked out early and understood if I had to leave early. He suggested that we talk when I got back home. I laid on my bed in my hotel room, just pondering and thinking about what all had happened. I would have only one more encounter with Darren months later, which I will wrap up in my little saga.....