The old “t4m” personals

On this sadly defunct personals website I used to always scan the “t4m” section in the hope of finding hot cross dressers on there. This one ‘girl’ used to say she gave free massages and I was a bit dubious but after a few months of seeing it I was in a really horny mood so I answered the ad. She didn’t have any pictures on the ad so I didn’t have high expectations.
She answered the door and it was very dark, coming from the light outside I was struggling to see but was trying to get a glimpse of her face. With just a few candles for light I could just begin to make her out and she was pretty large but I didn’t care, I just needed release. I was half hoping she’d just skip the massage and suggest sex but you never know with these hookups - sometimes you get a bj, sometimes a wristy, sometimes can can do whatever you want. She took one of my hands with both of hers and led me over to an actual massage table that was nicely set up and told me to get comfortable. I could tell at this point she was wearing a see through baby doll, thong and bra. I was actually really nervous but I took all of my clothes off and hopped face down on the table. I’d freshly removed all of my down there hair a few hours prior and wanted her to notice how smooth my ass hole was, hoping she’d put something in there.
To my great surprise she draped a towel over my back and began giving me a proper massage. After 20 or so minutes I began to question what I was doing here, was this all there was to it? I turned my head to the side and as she walked into my view I could see her erection through the sheer babydoll and barely there thong. I propped myself up on my elbows and reached out and grabbed her babydoll to pull her as close to me as she could go. She seemed surprised and took her hands off my lower back. I reached under the babydoll and grabbed her cock and started kneeling it in my hand. She said nothing, like she didn’t know what to do so I leaned over and put in in my mouth.

I couldnt deep throat her because of the awkward angle of the table but I had a firm grip around the base of her cock with my hand and I just kept sucking like a lollipop. I had the feeling that she wasn’t one to take charge so I thought I’d go for broke. I got up off the table and put her face down on the nearby couch. I straddled the back of her legs and pulled her huge ass cheeks apart so I could see her ass hole. I summoned up some saliva and then spat it right onto her hole, she knew at this point what was going to happen and she asked if I had a condom on. I said no so she pointed over to a side table where there was a packet sitting. I told her not to move while I reluctantly put one on and then resumed my position. I spat on her hole again and then and then pushed my cock right against her ass hole. It took a few attempts, she was flinching and clenching and not relaxed at all but eventually I got the tip in. When the tip was in I just stopped for a few seconds and let her get used to the feeling. When I felt her loosen just a little a slid the rest in, I think she was shocked by how far it went in. I started going faster and faster and I put one of my hands on the back of her head and pushed it down into her couch. I was kicking myself for having my phone out of reach as I really wanted some pictures of my cock sliding in and out of her phat ass but I wasn’t about to stop to go and get it.

I briefly considered pulling out so I could take the condom off and spray it all over her but I thought fuck it, this is about me and so I kept pounding until I had an enormous shudder and I moaned loudly to let her know I was done. She barely responded, she just didn’t see, to want to move. I said to her “great massage, thanks” and she just said “yep”.

On reflection afterwards I decided it wasn’t my greatest encounter but I got the release I was looking for. She ended up messaging me a week later to ask if I wanted another massage but I declined. I honestly felt a bit taken advantage of.