Tara has a Surprise for Me!

So a little about me, I'm 27 years old and a lifelong crossdresser, I'm engaged to an amazing woman, 26 year old 5'3, gorgeous curly, ginger hair, a great body and a personality to die for. We are both bisexual and have been together for 9 years, we discovered our sexuality years into our relationship and after a long talk agreed that we could both explore our bisexual sides, she can be with other women and trans women, and I can be with other men, trans women and crossdressers (essentially anyone with a penis)

Now onto Tara, Tara is a good friend of mine, we've known each other about a year, she's 23, around 5'8 dark brown hair, an absolutely amazing body, and we've always had some kind of a connection. Well recently I told her about mine and my fiancés deal and she seemed to be extremely excited about it, I assumed she was into my fiancé and wanted to shoot her shot.

She asked me to come to her place for a girly day and a catch up as we hadn't seen each other for a while. I excitedly agreed as it had been a long time since I've had a girly day; makeup, cute clothes and looking at hot guys on her dating apps was usually what we did on our girly days, nothing had ever happened between us, not that I hadn't thought about it, and with the chemistry we have I'm sure she had thought about it too! But aside from our agreement I was and am faithful to my fiancé.

So the day comes and I head to her place with a duffel bag full of my girly things, skirts, dresses, crop tops, my wig and a few other bits and bobs. As soon as I arrived she swung the door open eagerly, grabbed me by the arm and pulled me inside, she started to strip my guy clothes off (something she'd never done before) I was too shocked to stop her. Well in no time she had me completely naked infront of her, sheepishly covering my now hard penis. Then she just walked away and grabbed my bag, she rummaged through it for a while and then pulled out a tartan micro skirt, fishnet stockings, pink thong with matching bra, a cute black and red crop top and my dark red curly wig, she threw the clothes at me and told me to get dressed.

I quickly dressed myself and then she sat me on the edge of her bed and sat herself on my knee while she fixed my wig and then started on my makeup. At this point I was rock solid in my pink thong and worried she would feel it poking into her thigh, but she didn't say a word, just finished doing my makeup.

As she applied a thick coat of bright red lipstick to my lips, she leaned back and looked at me, locking her eyes onto mine. She leaned forward and I thought she was leaning in for a kiss but she went to the side and hugged me, she whispered in my ear "you look so good baby girl, those lips are gonna look so good wrapped around my fat cock".

Shocked by her words I pulled back and looked at her "what do you mean? The agreement doesn't include strap ons Tara!"

She grinned as she stood up, suddenly looking at me like I was a piece of meat, she shook her hips and under her skirt something hard swung from side to side under her skirt, I couldn't believe my eyes.

"Tara, seriously you know I think you're gorgeous and I love you but I can't cheat on my fiancé! Strap ons aren't part of deal, you're still a girl!" I said to her even tho I was still so tempted!

"Shhhh, Leah, just stop talking and let me show you" she said softly and her fingers slowly bunched up her skirt pulling it gently up her thighs.

The bulge under her skirt was straining against the material as she was just about to reveal the strap on she was wearing.

She pulled a little more and suddenly my jaw dropped to the floor as a big, 8 inch, thick cock and clean shaven balls flopped out from under her skirt.

"Holy shit Tara! I had no idea you were.... You have a.... Fuck!" I was flustered, excited and no doubt bright red.

She let her skirt drop back over her dick as she slowly walked towards me and climbed on top of me, straddling me as I sat, still in shock, on the edge of her bed.

She leaned in and kissed me with such passion, there were fireworks and butterflies in my stomach, but I couldn't help but notice the feeling of her smooth hard dick rubbing against my own.

She smiled into the kiss as she ground her hips into my thighs and then she quickly got up and pulled away, looking down at me she told me to get on my knees.

Without a seconds hesitation I slid off the bed and onto my knees in front of her, mouth open and looking up into her eyes in anticipation.

Staring down at me grinning, she lifted her skirt again, her huge girl cock almost hitting me in the face as it swung.

I couldn't wait, I reached up and held it with one hand and softly kissed the tip, and licked my way down to her smooth hanging balls and back to the tip before opening wide and sliding her into my eager mouth. I went as deep as I could before I gagged and pulled back slightly, she reacted by grabbing the back of my head and ramming it all the way down my throat. In shock my hand let go of her and found it's way quickly to her amazing soft ass, grabbing on for dear life as she fucked my throat. I managed to relax enough that I stopped gagging and my fingers found their way to her butthole, gently teasing and slipping a fingertip inside as she moaned. I could feel she was getting close to cumming so I sucked harder and danced my tongue over her amazing package and suddenly she stopped, pulled it out of my mouth and stood me up. She kissed me again before pushing me back onto the bed, I laid on my back looking up at her. She spread my legs far apart and lifted them as she kneeled on the bed. In one swift motion she removed my thong and grabbed a bottle of lube, she went to get a condom but I told her not to. I wanted it bare!

She lubed herself up the slipped a lube covered finger into my hole as I moaned like the sissy I am. Then she lifted my legs onto her shoulders and positioned herself "are you sure you're ready for this?" She asked, though it felt rhetorical.

"Yes please fuck me!" Was about all I could say with bated breath.

Slowly she pushed her huge dick inside me, pulling my hips into her as she pushed in. I moaned like a teen girl losing her virginity, it hurt a little but it wasn't long before it was just pure euphoria.

My breathing quickened as she pushed all the way inside me, until I could feel her balls resting against my ass cheeks, she waited a few seconds while flexing her cock deep in my hole and then started thrusting slowly, almost completely pulling out before going back in.

After a few gentle thrusts she picked up the pace, pounding my ass faster and harder than I'd ever felt before, my cock now limp and dripping precum as her thick, solid rod slid over my prostate with amazing rhythm.

A few minutes later my eyes were rolled back in my head, the only noises I was able to make were breathy girlish moans as I felt my orgasm brewing. I'd never felt anything like it before. It was as though my entire body was having an orgasm. My hole tensed on her cock as I let out a loud, almost pained scream of pleasure, my limp dick pulsing as thick streams of cum shot out, hitting me I the face, landing on my chest and covering all my pretty clothes.

I don't know if she just had amazing control or if it was because of my ass tensing but she started to moan loud and spasm, I felt her cock pulsing inside me and then felt the most intense pressure building inside me as her cum filled me up, pouring out around around her veiny member and dripping down my ass crack onto the bed. When she finally stopped she slowly and carefully pulled out of my ass, and immediately dropped down between my legs and started cleaning up my sissy hole, sucking up all of her cum, she then licked her way up my body and cleaned my cum off my face with a finger before sucking it into her mouth.

She looked at me, grinning and leaned in to kiss me, pushing her tongue into my mouth, both our cum sliding back ad forth between our lips. Eventually we had both swallowed all of it and she collapsed next to me on the bed, my hand instantly found it's way to her now softening penis as we fell asleep with her arms wrapped around me.

Thanks for reading! More to come!