Trans Love Is hard to find
- 9 days ago
- 17 min read
- 840 Aufrufe
I was always small for my age and always seemed more feminine than masculine despite the fact that I have a very small penis. I enjoyed feminine things, especially clothing and jewelry and upon growing up, I identified more as a woman than a man. I also was blessed with little to no facial hair in the traditional male sense of a beard or mustache. In fact, I had high cheekbones and ice blue eyes that contrasted with my brunette hair.
I really enjoyed wearing women’s clothes, especially panties and my tiny penis didn’t need the traditional pouch of a men’s brief. I learned how to apply makeup and walk in high heeled shoes and also learned the mannerisms of a female as they are quite different from a man’s. I could dress either part but felt more comfortable as a female.
When it came to relationships, I began dating women in college but it never felt right. I never tried dating a man until after college and often when I would identify with them early on that I was a woman trapped in a man’s body, they would run off or ghost me which was painful.
This continued for a few years until my late 20’s when I met Gabe. I was out with a few friends after work and was having a few drinks when a round was sent over. He specifically made the waitress say the drinks were from him and it was because of me. I have to admit I looked particularly cute this evening as I dressed in a navy Pencil Skirt, black nylons with red pumps and a white silk blouse with a camel hair blazer. My hair was shoulder length and my makeup was nice: not too much but enough. At this point of my life, I was identifying as a woman and dressing the part. And while many of my co-workers did not know, I had confided in a few that did and they were great about it! The bond of womanhood is strong, even as a trans!
Anyways, we accepted the drinks and before long, Gabe made his way over and introduced himself and asked to speak with me in private. I replied with my femme name of Sydney and I got up from the table and grabbed my near empty drink and we walked over to his spot at the bar. He said, “I can’t take my eyes of you. I noticed you from the moment I got here and have been mesmerized ever since. I am glad you accepted my drink and was wondering if you would like to have dinner with me sometime?” I could feel the rush of blood come to my head as he complimented me as I try very hard to be a woman and am glad he saw me that way but I have also learned that heartache comes eventually and since my mid twenties, I have been honest and up front about who I am so as to not give any false expectations or have myself put in danger when I eventually reveal my penis which has caused a few minor beatings in my life.
So, I said, “Listen Gabe, I am flattered by your compliments and grateful for the drink you sent over. I also think. You are cute and I would love to have dinner with you. But, before I do so, I need you to know something about me. I am actually a man but identify as a woman. As you can see I am not very manly but I do have a tiny penis and I want to say that up front so that you can run away now without embarrassment.”
He took a pull from his whisky and it seemed like he was trying to figure out the right words to say but when he put the glass down, he simply said, “I was drawn to you when I walked in here and the rest of it doesn’t matter as I think your honesty is admirable and your looks are amazing.” And he gave me a kiss on the cheek before continuing, “Your honesty took a lot of courage, especially since you don’t know me nor what my reaction would be but you are incredibly brave by telling me the most vulnerable thing about you without much passing of time. I would like to say that my offer for dinner still stands. We can figure the rest out as we go. Sound fair?” I gave him a hug as a small tear fell down my face and said, “Yes, I’d love dinner with you and I appreciate your sincerity.”
My friends witnessed it all and when I walked back to gather my purse, they were teasing me about hooking up. I blushed a bit more and as I told them I was going to grab dinner with Gabe they all said they would see me in the morning. My bestie, Cassidy, got up and pulled me aside and asked how it was going. I told her the sweet things Gabe said and how he wasn’t;t shocked that I was a woman trapped in a mans body and that he was open to seeing how things went. She hugged me and said I was very brave to put that out there so soon but it was the right thing to do if any relationship was going to happen. She knows about the past heartbreaks where I waited to tell only to be abandoned and heartbroken.
I met Gabe at his seat as he settled his tab and we walked outside and found a nice outside Bistro where, ever the gentleman, he pull my chair out as I sat down and pushed it in once seated. Our discussion was pleasant and nice and did not solely focus on my penis although he did ask permission to ask me a few questions about how and when I knew I was a woman in a man’s body. I answered honestly and openly and he seemed to appreciate the answers, I certainly appreciated his respect and kindness shown to me.
We finished dinner and we went to bar for a nightcap. When finished, I said I was going to go home and he offered to walk me there since it was just a few blocks away. As we walked, he was sweet in his gesture to hold my hand and over dinner he shared some vulnerable moments in his life that helped us bridge a relationship. At my doorstep, I gave him a kiss on the cheek and he promised to text and call me for another date soon. Although I was hopeful, I have had many a date end right here, just like this on my stoop.
I got into my apartment and looked at my texts. Cassidy had written a few asking how it was going and was he nice so I FaceTimed her and filled her in to say I had a nice time with a promise fo another call and Cassidy could here the dejection in my voice and said, “Sy d, stay positive, this time could be different.” I gave a weak smile and said thanks and signed off.
I woke the next day and got ready for work, I love to dress up for work as a paralegal so I put on a pink panties, with white nylons, white pencil skirt and navy silk blouse covering my pink bra (which I stuff with fake boobs that at least give me an A cup size) and threw on a red blazer and red pumps. I sat at my breakfast nook and sipped green tea while searching Instagram and my texts with little interest. My mind was on Gabe and if he might text, or better yet call. from my investigation of Instagram he hadn’t tried to find me there yet nor did I try to find him.
I packed my briefcase and headed out the door only to find a small bouquet of flowers and a card that read: Really enjoyed being with you last night, maybe we can grab a drink later? Same bar we met at. 6:30p.
I smiled and gathered up my flowers and brought them inside. I was smiling and happy and Cassidy picked up on it the moment i walked into work. She pulled me aside and asked, “What happened? Did he call?” And I said, “No but I walked out my apartment today and there were some flowers and a nice note to meet later today!” She hugged me at the news, and I beamed throughout the day with just a little more confidence behind me than usual.
Work flew by, probably because I was on cloud nine all day thinking of Gabe and I looked at the clock and it was 6:20p and I was still at work! I gathered up my things and walked the 3 blocks to the bar and showed up 7 minutes late. He was already at the bar, part way through a Jack and Coke. “Hi Gabe, sorry I am late. I lost track of time at work!”, I said. He replied, “No worries, I just got here a few moments ago myself. Can I get you a drink?” I answered, “Thanks and sure, I would love a Saphhire and tonic.”
We chatted about our days and I thanked him for the flowers and the nice card. I said it was the first time I felt seen and heard by another and he said he was so happy to meet me and loved our conversation that he thought about me all night and went onto explain that texts and calls are great but romance isn’t dead yet so sometimes flowers are the right thing to do. I blushed and leaned into give him a kiss on the cheek and said thanks.
After a few drinks, we decided that food would be a good option and I said I had some salmon and salads at my place if he was interested in coming over, I could cook for him. After all, I needed to thank him for the flowers. He agreed that this would be nice and we settled up and began our walk to my place which was only a few blocks away. We stopped at a local wine shop and I picked up a bottle of Chardonnay and had to fight off his attempt to pay saying it was my treat tonight.
We got into the apartment and I said I’d be right back but to make himself at home. He uncorked the wine while i freshened up and I was greeted with a nice glass of Chardonnay when I got back and an even nicer kiss which was on my lips this time and Gabe even slipped me a little tongue as he pulled me tight into him. I accepted it and gave a little tongue back.
As I made dinner, Gabe worked his iPhone to play some great music and I discovered we had a lot in common musically and personally and a bond was developing between us. I cooked the salmon in the air fryer and tossed together a salad. While it was cooking, I excused myself and said I was going to get into something more comfortable than the 6” heels I was wearing all day. Gabe smiled and said he’s man the air fryer and I whisked away.
I got to my bedroom and took off my work clothes. I put on a pair of Nike Epic Lux run tights (no panties) and a Nike sports bra (inserting my fake boobs) and covered up with a crop top sweatshirt that showed off my abs and put on some socks before heading back out. “Comfortable?”, Gabe asked and I replied, “You have no idea how uncomfortable heel are!” And he laughed and said, “No, I do not know that feeling!” Ding went the air fryer and the salmon was ready. I plated it like a professional chef and delivered it to Gabe who commented on the delectable dish in front of him. We noshed and talked and enjoyed each other’s company. When we finished we shared another glass of wine before he insisted on clearing the table. I couldn’t let him do it alone so I helped and in no time we were finished.
He put on some Al Green, Let’s Stay Together, and asked me to join him in a dance. We slow danced and my 5’4” fame fit nicely against his 5’11” frame and we rocked the song away with my head on his chest and his hands on my exposed back. He felt nice against me.
The song ended and he leaned in for a kiss and I kissed him back. The next romantic song kicked in my I couldn’t hear it with my heart pounding so fast. Out tongues danced with each others and my passion was intensifying as I hadn’t been in this situation in over 3 years. He seems calm and collected and I admired his poise. Slowly his hand found my ass and he squeezed into it, I let out a small moan and pulled back. I stared into his eyes as I lowered my tights and just gazed at him. I got them below my 1” cock and pulled them off, waiting for him to laugh or run away, but instead his eyes never left mine and when I pulled my top off, the same thing, he was locked onto my ice blue eyes. When I pulled my bra off, the fake silicone sones fell to the floor and he did laugh a little at that but only because one bounced off the table and knocked my empty wine glass over.
Naked, vulnerable and very scared, I stared into his brown eyes. He walked toward me, without looking anywhere but into my eyes, leaned in and gave me a kiss and said, “Wow, you look amazing!” And gave me another kiss. I almost wanted to cry as I have never been this accepted by another. As I kissed him, I undid his belt and pants button. I pulled his shirt off and exposed his chiseled chest where I sucked on his nipples while lowering his pants. He shimmied his hips and they fell to the ground and he pulled them off of himself using me as a slight balance bar while kissing me. I cupped his cock through his Calvin Klein Black red trunks and felt his stiffness for the first time.
I pulled him into the bedroom and tossed him on the bed. I climbed on top and kissed him and lowered myself slowly kissing almost every inch of his body but focusing on his nipples, stomach and belly button. He enjoyed my teasing him and did not stop me when I pulled his trunks down to release his 9” clean cut cock. A nicely trimmed pubic area was also a bonus and as I leaned to the side of him, I stroked his cock. He never stopped staring into my eyes and a deep connection was there between us. I kissed him all around his cock, the tip, the shaft, the base, the balls and teased him for a moment before I licked him up and down and then inserted him into my mouth. I enjoyed his cock and slurped on him. Saliva dripping everywhere as I increased my rhythm. Fondling his cleanly waxed balls and I wicked him off. He shut his eyes and just enjoyed the pleasure I filled him with.
I pulled off him and climbed up to kiss him. We parted from the kiss and he said, “I’m sorry but I h ave to ask a question that I am not sure how to ask.” I said, “You can ask whatever you want, you have always been respectful and I know what we are doing may raise a few questions so just ask. You won’t upset me. I promise.” And with that, he asked, “Do you like blowjobs as much as I do? I have never given one but I could try. And as for sex, I assume anal? I have never done that either.” And I replied, “Yes, I like blowjobs but my penis is very small and if you aren’t comfortable with it, I understand. As for sex, yes, anal and I can help you.” He replied, “Thanks, I think I will pass on the blowjob for now. But ready for anal.”
With that I rolled over and grabbed a condom and some lube from by nightstand. I gave him the condom and he rolled it onto himself and I took the lube and squirted some into my hand and rubbed my asshole and then rubbed his cock. I said, “Go slowly and be gentle please. We can increase speed after a while but I need to get used to you.” And I laid on the bed on my back and put a pillow underneath me and then I spread my legs wide, my tiny penis looking more like an enlarged clit. Gabe hopped off the bed and got between my legs and lowered his stiff cock and guided it towards my butthole. Having found it, He used both hands to insert his enormous 9” cock into me. I hurt a bit at first since even my vibrator isn’t that large but soon my asshole expanded large enough to allow him in.
He slowly pressed into me and I tossed him the lube which he strung across his shaft. He’d insert a few centimeters and then pull out. Coat with some lube and try again. The lube coated my walls and I soon felt most of him inside me before he asked, “Are you comfortable?” To which I replied, “Yes, you were nice and gentle, thank you!” “I am not all the way in, can you handle more? It looks like maybe two more inches.” “Yes, but go slowly.”, I say and he pumps more lube on his shaft and drives into me deeper and slower. He hits his hips against my spread legs and says, “There, all the way in. You okay?” And I reply, “Yes, give me a second to enjoy you inside me before we get into it” and I relax with all 9” of his stuffed in my ass, filling me with cock and happiness for the first time in my life.
O let go of my legs but keep them raised and spread and motion for him to begin and he slowly pulls out of me and then back in. Slow, full of sexual energy as his stiff cock fills me completely. I lower my hand to play with my tiny cock and when it stiffen it maxes out at 1.5” and jerking off with two fingers is like jerking off with tweezers but its all I know so I enjoy it. Gabe increases the intensity with his thrusts and soon works up a pace. Sliding in and out of my lubed ass while he presses against the back of my knees and holds me open for his fucking. I stroke my cock.
We fuck for a while and I like his stamina and his pace. My asshole getting the pounding i have craved and I squeeze my buttock to tighten the grip around Gabe’;s cock as he fucks me. The increased pressure on his cock works and he thrusts into me one final time before grabbing my legs and pulling himself tightly against them. His throbbing cock feels so good in my ass as he empties his seed. The pulsing action presses against my colon and prostrate and the precum leaks out of me furiously, creating a nice lube as I work my tiny penis to cum on its own and I release a two large ropes of cum across my stomach and chest.
Gabe slides out of me and leans in for a kiss. The cum on my chest temporarily gluing us together. I slide his condom off and pull the opening up to my mouth and drink his seed. I love the taste of cum and Gabe’s is a healthy portion. I kiss him and we cradle back into bed and lie side by side naked. Me resting my heads on his chest as drips of lube seep pout of my ass.
I give him one last kiss and head to the bathroom to clean up. I come back with two glasses of wine and find Gabe sleeping. I take a warm wash cloth and wipe him clean but he doesn’t wake. I give him a kiss on the cheek and curl up next to him. We wake the next morning and I thank him for his support and kindness in bed last night and he thanks me for the most wonderful night ever.