My First Translesbian Encounter

He came over sometime around 6 and wanted to change at my place; that was fine of course. I totally understood. I wouldn’t want to risk anyone I know seeing me dressed all feminine. I’ve always been discreet. Jen and I met through craigslist and after a coupe weeks of emails we finally decided to meet at my place.
I honestly expected her to look a lot more feminine, but then again on her emails all I ever saw of her was her neck down dressed in lingerie. i did not expect some tall broad shouldered stocky guy with spikey hair to show up.
I’m not too into men, and although i would totally have sex with a guy, it was just odd meeting someone you weren’t expecting…. I didn’t want to turn her down, plus I was looking forward to a few hours of sex I’ve never had before.
I put a bit of eyeliner and mascara on before she came over, and had my panties, stockings, and chami combo on under some loose pajamas when I had gone down to meet him. He finally texted me saying he was in the parking lot. I went down and saw him looking way too much like a him, but whatever I thought I might not be as feminine as I am told I am.
He showered right when he got there. Which was a reassuring site, he was very clean. W even wore condoms during our oral sessions. She requested i prep things a bit while she was in the bathroom showering and getting ready. I undressed a bit and put some lip stick on. She brought over a toy, a rabbit vibrator, but that was being saved for when she got out. I pulled out my extra large sharpie moistened it up with my mouth pulling my thong panties out and to the side and slipped it inside me loosening myself up for her.
She came out of the bathroom finally, clean and dressed in a corset and garters attatched to stockings with a pair of lacey black panties she borrowed from me.
– She also re-geled her hair… it was a bit awkward, but I wanted it.
She came out and looked at me approvingly as I continued masterbating while she watched. Going towards her bag she pulled out her purple rabbit still in the box and a condom. wrapping the condom on the toy and getting it ready. She sat next to me and looked for a minute at the porn I put on for us, we got closer to eachother. She put her leg on top of mine and we began running our legs up and down eachother. Our lips met and our tongues crossed a bit. Lots of tongue, I love that about making out with cross dressers always lots of tongue.
Without words she walked over to me and knealt inbetween my legs kissing my thighs licking the sides of my second most sensitive area and then she started sucking and licking me 😉 After a whole I stuck my ass forward a little hinting for her to show me her toy.
Jen continued jacking me and sucking me off while playing with my sharpie. Having my legs up and on her shoulders while she ate me out fealt so natural to me. Everything was so fluid and so hard. It wasn’t like having sex with my old girlfriends. All the nerves, and wanting to pleasure the girl. I get so bored when having sex with girls, it doesn’t do anything for me like it did when I was in highschool. This was still new to me but I loved that he was in lingerie, and had a cock and was sucking my cock.
It was all so relaxed, worry free. Although I fealt like I was being pulled into a vacuum, I never had a blowjob so intense.. finally pulling out her toy after lubing it up she was beginning to push the vibrator inside of me.
It went in quite easily even if it was 3 times the size of my sharpie. He spoke softly to me asking if it fealt ok, trying to gauge if she can go a bit harder. I said it was ok as she began to adjust the rabbit so it began swirling around inside of me; Jen was now pounding me with her new toy and wow did it feel amazing, I fealt so relaxed and turned on, my cock was throbbing in her mouth. Being sucked while she was fucking me with this large vibrator was an out of body experience for me. And the best was yet to come
. She wanted to fuck me now, but requested that I do a favor for her a bit first. I said &#034,of course anything.&#034 She looked to the ground asking me with her eyes to get on my knees. I nodded as I rested my knees on the ground and faced her. Pulling a half way stiff cock out of her panties, I was amazed she was as big half mast as I was fully erect.
I wrapped my lips around her taking her in once, out, then twice more; puling her head into my mouth and resting it on my tongue sucking as she got harder. It already was hard to fit in my mouth when it was limp and now my jaw was already getting tired. Idk how actresses keep up, it is hard work. I like average size the most:)
She said she was big but I didn’t expect her to be that wide as well. I used a bit of teeth on accident and he took it away from me, he spanked me and said to watch my teeth. We went a bit again as he tried fucking my face, but the same thing happened. I honestly didn’t know much about what I was doing, even if I have one too. It was so much harder with how large he was. Eventually I got the hang of it for a bit and she decided she wanted to put herself inside of me now.
I lied on my stomach atop the pillow she lay for me on the bed as she put a new condom on and lubed her tool up. I knew I was in for some good sex after all that foreplay. He was just too good at it, and seemed like he’s had a lot of sex before. it had been a few minutes since my pussy had been played with and I still fealt good from when he was toying it before so I started fingering myself a bit.
he came to the bed and pulled my ass up and into the air. Caressing my smooth butt and feeling my upperthighs and lower back. Then something fealt very odd to me at the time. But it turned me on in such a new way. She pushed her hand against my upper back and into the bed forcing me to arch my back. I fealt humiliated in a way, like I was being put in my place. But I liked it. She pulled down the shorts I had put on again so she could take them off again. and then she slowly pulled my panties to my mid thighs when I stopped her and said I would prefer they were just pulled to the side. It’s sort of a fetish I have, I love panties, the way they feel and look, some of you know…
She pulled them back up and pulled the string of my thong around my cheek; leaving the bow on my panties to rest atop the lowest part of my back. She began pressing her head into me as I began to squirm. He was sooo big. Smack, her hand went across my cheek, she said to keep my ass up. I went into the position and she put me into it, this time she went in a bit deeper until: the same thing happened. massaging the spot she had just smacked on my ass she pulled me up against her pushing my front half into the bed again, a bit further in and her head was definitely inside of me, she thrust in a little deeper pulled out a bit then in a bit more working her way out again loosening me up. It was soo much nicer having a real penis inside of me as opposed to a toy. Ohhh how I moaned, it was like a whole new voice coming out of me. It didn’t sound masculine at all. spanking me again she thrust me into the bed, telling me how tight it was spanking me twice more. &#034ohh…ohhh…ohhhhh&#034 I moaned. I didn’t care who heard us in the apt complex.
That’s when the fun really started happening. If I thought the foreplay fealt natural and intense it compared little to this. While being spanked and fucked was amazing it was nothing compared to the smacking of his body against me. Slap smack slap smack, the neighbors could definitely hear all of this. I fealt like the liquid that was dripping from my cock through my panties. I held my self so loose as he hit just the right spot.I was taking it like a natural. I fealt like I could cum at any moment and like I was cumming the whole time.
I touched myself a bit, then she reached around and touched me.
I wish it would have continued, I wish I could tell you we climaxed together shortly after. I wish She would have went until she came inside of me, but she wanted some too. She pulled out, pulled off her condom and cleaned himself up in the bathroom.
She said to get hard and put a condom on, her turn was next.
I could barely walk let alone let her have it. My pussy and legs fealt like they were vibrating and my pelvis kept thrusting forward on its own.
She came out of the bathroom and knelt up on the couch. She had no panties on and I pushed against her limp but I couldn’t get hard at all. I thought maybe I could get hard if I tried pushing it in. The opposite happened. I tried and tried until the condom was too loose to even keep on. she tried sucking me and had gotten me half way there, we tried putting it in again. I said she could fuck me again but she said we were out of condoms.
She decided we should finish and jack off on the couch together to the porn that was still playing in the living room. We were on the couch together for maybe five minutes making out and masterbating when she was showing signs of being about ready to cum. She got up and asked where I wanted it. I still wanted it inside me but that wasn’t gonna happen…I didn’t want his cum at all anymore. Something about everything was starting to make me regret what I had just done. I didn’t even cum and I was starting to feel guilty.
I wanted him to just go, but I didn’t know how to say it. She asked if i wanted it in my mouth i nodded with a sinking feeling in my stomach as she pushed herself inside my lips and began to cum. I could not believe what I just did. I fealt so…dirty, in a real way not the porno ‘ooh daddy kinda way. She wanted me to cum then but i just couldn’t. It was such an odd ending to what seemed was gonna be an earth shattering orgasm I kept jerking myself sitting there so empty headed and unsure of how everything worked out.
She changed in my bathroom and cleaned herself and came out looking no different then he did before when he was in lingerie.. We talked some small awkward talk as he put his shoes on and gave me an empty kiss as he said I can keep the toy and he hopes to see me again.
I threw away the toy the next night. He emailed me incessantly after that, asking to take me out. He wanted to become frequent sex partners and take me to but lingerie and take me clubbing and out for dinners. Saying he wants to get more into cross dressing. Sounding kind of manic about the whole thing.
Maybe I was the bitch in the situation. But I was looking for an intimate encounter. Not to be dominated by some guy. It was awkward, even though the sex was great, he gave me bad vibes. Like he would be quick to anger and would show up at my door unannounced. We haven’t met since. Part of me still wants to though. He was a good lay, and he might just look at sex differently…
Ideally I would like to just lay in bed with another cross dresser, intoxicated watching a movie, maybe doing something girly like listening to bad pop music and painting out nails. Dry humping through our panties. making out then sucking cock. Toying and fucking. Spanking pulling hair, biting, licking, feeling. I want rough play, I just want it to be more feminine and with someone that gives me good vibes.
*ps I have met with someone on here, and I want to clarify this was with the first cross dresser I met. you were amazing