A Trans-Lesbian Montreal Love Affair

Credit https://www.gaydemon.com/ Cari Christi

St. Catherine’s Street in downtown Montreal is one of the world’s most vibrant streets and entertainment corridors. Known for its energetic, exciting and often crowded venues, it is lined with quality restaurants, theatres and many popular nightclub establishments. St. Catherine’s Street attracts a diverse and generally sophisticated group of patrons. I love this area and decided to go out much earlier than I normally do in Montreal.

When I entered this quite ‘unique’ club on St. Catherine’s street to get myself a drink or two, I tried my best to saunter alluringly yet as subtly as I could in my very high heels toward the oval shaped bar. I was perhaps quite a bit ‘overdone’ in my manner of dress. I really loved my quite short, skin tight, black cocktail dress, and the short matching black jacket I wore that revealed my very teensy, narrowed waist. My 5′ sandal style, slightly platformed alluring black leather almost spiked high heels made walking with a sexy sway easy yet also a bit challenging! My long blonde hair was even a bit teased to add to my seductive appearance, yet as I strutted through the early evening after work crowd, no one even seemed to notice me.

I sat down and got comfortable where there were a couple of empty barstools and crossed my legs seductively. I removed my little cover up jacket purposely revealing my smooth arms, chest, and what appeared to be quite a bit of cleavage between my soft breasts. I was quite the tease with almost all of my smooth, sexy thighs and black very sheer silk stocking covered legs exposed as well. I felt so very sexy and sensually energized yet I had to go out of my way to get the attentions of the young female bartender to get me a drink. This is just one of so many reasons why I loved Montreal. A pretty gal dressed to the nines – even in 5′ ‘love me’ heels doesn’t cause a ruckus or even a stir walking alone into a bar or a club!

Once I got my drink I visually surveyed the crowd. Opposite me on the other side of the bar were several guys and several young ladies loudly drinking and talking. One of many interesting things about this bar is that it is straight, gay, and all in between. Girls come in with girls, guys with guys and guys with women. Sometimes it is fun just trying to determine who is with who and if any of the women are transvestites or even transsexuals or in between. It also works the other way here as some of the women are trans guys or may dress to look like guys. I once met a lesbian woman here who wanted to take me home to ‘dominate’ me! This club (Che Mado) is at the least a very interesting place to visit and people watch!

This club has drag shows late at

night, dancing and all kinds of wild entertainment. Being only about 7:00 PM, I liked seeing how the club transitioned to the evening crowd. I was on my second drink when a most gorgeous young, slim, blonde haired woman entered the club and came in and sat down right beside me on the only empty bar stool. I kept wondering if she was like me. She was stunning, but less overly made up than I and dressed – much like myself. She too had very bold, bright dark red lipstick; a short stylishly uneven hemmed black dress and black high-heeled pumps. She was so very strikingly pretty and she looked like a Dallas Cowboys Cheerleader with her bright smile and polished, attractive good looks.

I just had to talk to her and I complimented her on her sexy heels! I was actually quite stunned and taken by her beauty and I must admit I found her very, very, attractive. We began talking and we both remembered that she and I had met once before a couple of years earlier at Café Cleopatra’s, one of my most favorite Montreal Clubs. I remembered that when we talked, that she was apparently very ‘straight’, had a girl friend and dressed for the love of experiencing the dressing and for the feelings of femininity.

What a shame I thought, because I remembered back then that I would have loved to have the opportunity to take ‘her’ to bed! I like trannies generally more as friends and usually not as lovers. I like being with a man as a woman and generally don’t find my feelings towards fellow trans girls to be sexual, but this ‘gal’ just made me crazy. There was a true lesbian inside me! There were just so many things about her that I so liked. She was everything that I was yet she was most likely far more ‘innocent’ than I. Her naturally lithe and slim shape was even more fem than mine. Her face was beautiful and her clothes just fell perfectly on her petite little figure. She would have looked great in a burlap bag but I was imagining her naked in my arms!

I had the opportunity to talk with her and I coyly flirted as we spoke. I know that ‘we girls’ love flattery – especially if it is done in a ‘tasteful’ manner. Eventually we talked about some of the people at Café Cleo’s and ‘Shanna’ became more animated, enjoying the subject of some of the characters there. Shanna even let it slip that she had been ‘seduced’ by one of the very pretty trans girls there and I knew that I had a very good ‘shot’ at seducing her if I played my cards right! I could tell that she found me attractive and sexy by her returned compliments. She said things like ‘I bet the guys love getting into your panties’, which certainly led to more intimate discussions about sexuality, that soon found the two of us getting a wee bit ‘hot’ and bothered!

I coyly suggested that she see the reflection in the mirror on the wall of the two of us. ‘Don’t we look hot? I don’t think I’ve ever seen two sexier lesbians girls together!’ Shanna laughed and enthusiastically agreed. When she put her hand on my thigh as she agreed, I swooned in sensual excitement knowing that I would end up in the sack with this previously untouchable beauty. I offered Shanna another drink and she graciously accepted. I could tell she was even more of a submissive than I. By buying her a drink I had apparently signaled that I was the pretty ‘top’ and she the even prettier ‘bottom’.

Soon our hands were on each other’s thighs and we began to talk about what we liked in bed! I was getting so hot about our honest, sensual discussion that when Shanna made a comment about how sexy my lips were, we ended up in the hottest kiss I’ve ever given a woman. Unaware that we were making quite a spectacle, our swirling, dizzying French kiss lasted for almost a minute. When it ended we were so hot that we found the comments made by a patron across the bar to be quite amusing. ‘Get a room ladies! Can I come and watch!’ We laughed and hugged enjoying his perverse but amusing comment. We would be getting a room though. We soon tried to subtly escape the bar and we soon headed off to my car for the short ride back to my hotel.

The ride was a silly almost panic like, hands all over each other, almost dangerous drive with the two of us ‘girls’ in heated need. I hadn’t wanted any one so badly in many years. I felt like a girl in high school who had held back her feelings for her girl friend for much too long. I wanted the soft perfumed skin of this stunningly feminine transgendered woman in my arms soon! We parked in the underground garage and took the elevator to the first floor where we would take another elevator to my room.

Shanna was just a bit too tipsy to be in any way embarrassed by the fact that she was walking arm in arm with another woman directly through the lobby of my hotel. Another couple prevented us from another heated kiss in the elevator – but I could only imagine what they were thinking as we had such affection for each other as we left the elevator on my floor in a tight side by side embrace. Once inside my door we both relaxed and smiled. As ‘girls’ we knew that slowly was beautiful. We had some seriously powerful ‘feelings’ and we wanted to show a truly graceful appreciation for how we felt for one and another, yet we so wanted to begin!

Leaving our pocketbooks on the table of my condo style hotel room we once again kissed. This time we had no worries that we were being seen and our appreciation for each other would be genuinely expressed. In retrospect I now realize that woman-to-woman sex is very emotional and feelings based. We were both very attracted physically and we were emotionally very in lust as well. The two of us ended up on the bed covers and with our mouths pressed together in genuine passion. The power of the feminine feelings between us was immense. Her lips were so soft, her body so lithe and she was melting just as quickly as I. I found myself gently running my hands on her stockinged thighs. Shanna was already moaning in great pleasure. This was a coupling that I would cherish!

As needy as I was and as much as I wanted her, I wanted it to be beautiful. My caresses were teasing and even though I was more of the aggressor and Shanna the more submissive one, I was exquisitely gentle and as soothingly erotic as a ‘girl’ could be with another ‘girl’. My touches sent chills up both of our spines and we were still fully clothed in our ‘girly’ club outfits. Eventually I slid the spaghetti strap of her dress down to her arm and then did the same to the other. This made Shanna breathe even more heavily and softly groan. I slowly slid her dress down exposing her black, strapless bra. I kissed her chest above it and Shanna was clearly moved. I reached to her back and found the two hooks and deftly undid them. I slid off her bra and looked at her beautiful face. She had her eyes closed but was smiling and in delight. My mouth went to her very boyish left breast as I licked her nipple before gently suckling it. Shanna was clearly enjoying her ‘girlfriend’s’ gentle advances.

When I went to her other breast Shanna was soon struggling to slide off her dress. I helped her while still gently licking and sucking her breast. We slid her dress off as my lover was now only in her garter belt, panties, heels and stockings. What a beautiful and stunning, smooth, sensual shape she had. Her waist was tiny and the somewhat tight garter belt made it look even smaller. She was ‘tucked’ like I because her teensy string see through panties were flat against her light colored pubic hair. I knew how badly Shanna wanted more, but I had to tease this beauty beyond madness. Every little trick that men had used on me, I now found myself using on her. I kissed her breasts and then her belly. I kissed her panties and licked the edges. She wanted me to pull them off, but I wanted HER to pull them off. My teasing brought me what I wanted. She was so hot that she pulled them off, spreading her legs enough that the very suddenness of the surprise that sprung out inches from my face had me wide eyed and so very pleasantly shocked and amazed!

Shanna was a huge girl! Her cock was dripping wet. It was at least eight inches long and quite thick. The head of her beautiful cock was perfectly circumcised and larger than her shaft. I never wanted to taste a cock more, yet I still wanted our coupling to be perfect. I touched her large balls and gently rubbed them as her cock jolted and jumped from my touch. Shanna was lost in delight and heavy breathing. She was cooing and mumbling ‘Oh God’ repeatedly. I was having just the effect that I had hoped. She was so dreamy to me and my every action and caress was eliciting her verbal begging’s for more. I had her just as I wanted.

When I first met Shanna a couple of years earlier I knew I wanted her and was so disappointed to learn that she was ‘straight’. I of all people know how girls can change, because I too once believed that I was quite straight as well. This fantasy was now a very beautiful and incredulously sensual reality that was spinning into true sexual joy. The dreamy, steamy girl I couldn’t have was now begging for my every touch and caress!

I can be a very good tease! I gently licked her perfumed balls and ran my tongue up her long, dreamy shaft. When I licked her cock head it jumped and she squealed in delight. My passive little lesbian partner was soon cooing ‘Oh Yes Cari, Oh Yes!’ We both knew what she needed and what I needed to do for her! I know that sometimes I can get so ‘lathered’ in need that even a touch to my cock can elicit a quite premature ejaculation. I didn’t want the to happen here and I suspected that Shanna was already in quite a state. I decided that I would firmly hold her balls while I tasted her cock head and Shanna’s moans were just incredulously needy. I sucked her delicious tasting cock head gently, though I so wanted so much more of it in my mouth. We were both so close to orgasming and so excited by our coupling. It was time for me to get undressed.

‘Don’t move my darling’. I cooed, knowing she wasn’t going anywhere! I got off the bed and stripped down to my stockings, heels and panties. Shanna loved what she saw. Her ‘lesbian girlfriend’ was as sexy as she. When I embraced her in another steamy kiss atop her, her hands were running all over my body and my derriere. ‘Fuck me my sweet!’ Shanna whispered in my ear. It seemed quite natural for me to do so and I went to my pocketbook to search out a condom and lubricant. Now that I was both lubricated and sheathed, Shanna was already spreading for me as knelt on the bed. We were face to face and I easily found her opening. Gently rubbing my own eight-inch cock against her button, I spread the lube as I spread her for my entry.

This ‘girl’ who was once straight, wanted my cock as bad as I loved getting cock. My gentle presses against her opening allowed her to wiggle her opening to meet my pulsingly erect cock. She gasped as I entered her and let out a yelp and cry. Instead of asking me to go slowly, she grabbed my naked ass and pulled me into her. My cock was already half way inside her and she was chirping like a bird in spring. I teased her at first, but she clearly wanted every inch of my cock in her ass. Soon my gentle thrusts found my balls against her opening. Shanna was groaning deeply in guttural groans and in deep passion. ‘OH Cari! Fuck me more my darling! Oh Yes, Oh God yes! Shanna cried as I began to pound her inner ass.

This was getting to be too much for me. I hadn’t enjoyed the position of top in years and my control was waning. I was afraid I would ejaculate when suddenly Shanna began to shake and quiver uncontrollably. She was orgasming and I felt her sphincter grab hold of my cock like a powerful elastic causing me even more duress. Now as I fucked her wildly her ass and sphincter were milking me to the most immense orgasm that I’ve felt in years – without a cock inside me! Shanna was going wild and literally screaming like the world was on fire. Her head was waiving back and forth wildly and she could only squeal deep guttural sounds from her mouth. I could tell that she was moved perhaps to a level even far greater than me!

I collapsed atop her and we kissed sweetly and deeply. ‘Lesbian love’ was so real and so wondrous. Shanna was thrilled and moved. She wanted more. Soon she was removing my condom and placed me on my back. She then proceeded to try to torture me in the same wondrous way that I had seductively electrified her. Now I was once again hard and we went to a side-by-side 69 position. I sucked her cock and she sucked mine. It was almost like a contest to see who could do the better job of pleasing. Shanna may have been a little new to tri-sexual love but she could truly suck cock like a whore. Her enthusiasm drove me wild.

It was the ultimate erotic, yet confusing ‘lesbian’ scene, only the girls had big sticks between their legs. With both of us in only stockings, garter belt and high heels we looked quite feminine in spite of our large pulsing erections and our under-developed breasts. Shanna loved sucking my nipples and breasts and it drove me wild. I would become the first ‘girl’ with more, that Shanna would fuck in her young life and taking that incredulously long and thick ‘manhood’ of hers as I got on my hands and knees was wondrous. She had incredible staying power and after many minutes of spanking my ass with her balls and filling my ass to the brink, I had to beg her to stop before I orgasmed long before I wanted to.

I wanted to sit on her cock so that I could be face to face so we could kiss with her cock deep inside my ass. It was beautiful and so sensual as I humped her cock feeling the magic all the way up my ass so deeply inside me, all the while kissing this beautiful, erotic, feminine creature with a cock every bit as large as mine. It was inevitable and we both felt and sensed the closeness of our need and coming eruption. Our orgasm was unforgettable and so magical. I’ll never forget it! My cum spewed all over her soft, stomach and small boyish breasts and Shanna reveled in rubbing the cum all over her chest like it was a healing, magical cream. We were truly loving and appreciative of each other. I had found a sister, a lover, and a true ‘lesbian’ lover.

With Shanna I had found a big piece of heaven. Making love to a beautiful, friendly, delightfully erotic woman with a huge cock was as good as any experience in my lifetime. Shanna and I still meet when I travel to Montreal. I am welcome at her apartment in drag or not. We are truly ‘sisters’ and lesbian lovers of the tri-sexual kind. We both inspire each other and the best part is we can share dresses, go out to a club, and then come home and make love. It is such a different way to think about ‘love’ and the world as a cross dresser / transgendered person. Someday I’ll tell you about the time we took a very luck guy back to her apartment! When I visit Montreal we always go out once or twice together. As much as I love the affection of a good man, Shanna truly brings out the woman in me!

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