Fall 2001, 21 yrs. Old
Not everyone I met at Sandie’s took me to bed. Some came here out of curiosity. Not all were referred by Jo. Alex vetted most the men who came up to me. I only dated a guy if she nodded he was okay.
One evening, a slightly balding, short, portly man came up and offered to buy me a drink. Alex shrugged she didn’t know him, but I smiled and mouthed this one was okay. I knew him: he taught history when I was a freshman in high school.
Mr. Smith was a funny teacher and I liked him a lot! I could see a glimmer of recognition in his eyes. I introduced myself as Angie and motioned him to sit. He looked uncomfortable. I smiled amicably and chatted, trying to put him at ease.
“You remind me of someone I taught,” he said. “You’re Andrew!”
His eye went wide with fear, and he started to rise.
I patted his hand and said, ”I go by Angie, now. I’ve been transsexual four years now.”
I smiled and talked about how much I’d enjoyed his class. I asked about his current life, but avoided mentioning his wife. I was suddenly curious about him in bed. He stayed nervous, so I asked if he’d like to come to my place for coffee, or a glass of wine. We could catch up in private.
He jumped at the chance and drove me home. He didn’t really calm down until he got in the door. I poured some wine and sat next to him on the couch, legs tucked up under my skirt. He kept staring at me, not believing who I was.
I excused myself and changed into a light, sheer robe. His eyes nearly popped out of his head! I sat back down and let him look while I tried calming him more. Finally, I made the first move. I slid my robe off my shoulders and let him see my breasts.
“Would you like to fuck me?” I purred.
He gulped the rest of his wine and nodded yes. He rapidly undressed and stood before me. I was impressed with what I saw. He had a fat, seven inch cock rapidly springing to attention! I grabbed his cock and led him to my bed.
He explored my breasts with his hands and mouth. He looked at my cock with interest, but didn’t do more than stroke it. I purred when he did. I gave him my lube and asked him to prepare my ass. I lay on my back and raised my legs. He stretched me painfully, at first. I gasped, but begged him to push all the way in.
After a few thrusts, the pain faded and I felt a warm feeling as he fucked me with a steady pace. I held him close and wrapped my legs around him.
“You feel sooo goood in my ass,” I whispered. “I want you to fuck me harder! Take me!”
He picked up the pace and buried his fat cock deep in my ass. I was losing myself to the wonderful sensations I felt. (Did I mention I REALLY like anal sex?) He rode me hard! I hurt, but wasn’t going to stop him. I like feeling sore after a good fucking!
He rode me for nearly an hour before he filled my ass with his load. Some leaked out around his cock. I asked him to stay inside me as long as he could.
When he finally pulled out, I moved down and took him into my mouth. I couldn’t take much, so I licked his balls and his shaft, flicking my tongue over his head. I was kissing the head, my lips parted when he filled my mouth with his load. I swallowed it all.
Shortly after, he dressed and went home.
A few days later, he called and asked if he could come over sometime. I set a date and asked him to supper. I knew he was too nervous to be seen in public with me. After supper, we stripped and I led him into the bedroom. He stopped at the door and gave me a nervous look. He hesitated, then finally, quietly asked a favor.
“I’ve always wondered what it would be like to take a cock in my mouth and in my ass. Can I suck you? Would you fuck me?”
No man had ever asked me to fuck them before! I’m a “bottom”and prefer it that way. I have screwed a couple of women and some other transsexuals, but I’d never even thought of fucking a man.
I lay on my back, legs spread wide, and dangled my cock ininvitation. He crawled between my legs and kissed the head . He licked the entire length a few times then took me into his mouth. I quickly stiffened in his warm mouth!
Mr. Smith slowly bobbed up and down, sucking lightly. He’d pull all the way up, his lips parted slightly at the slit, then slid all the way down. He licked my balls. His technique was electrifying! I could feel him smile when I told him how good it felt!
He shook his head no, my cock in his mouth, when I asked if I should warn him I was coming. I hadn’t played with myself for a few days and soon filled his mouth. He swallowed all my cream and continued sucking a little longer.
He beamed when I told him how great he did! He told me he fantasized about giving head for many years, but feared approaching another man. He’d only worked up the nerve to ask a tranny the night we met a Sandie’s.
“Call me when you feel a need to suck cock,” I said. “You can suck me all night, if you want! This can be our secret!”
He brightened at that, the rolled onto his stomach and spread his legs, then his cheeks, asking if I’d fuck him. I was looking forward to this. He was offering me his cherry asshole! And I wasn’t going to let it go to waste!
I lubed my finger and teased his sphincter, tracing the edge, circling it. He moaned in pleasure and my small cock grew harder. (I grow to a little over 5 inches long and an inch and a half thick when erect, the rest of the time I’m only about two and a half inches long). I pushed the tip in past the opening pulled back out. I finger fucked him like that a few minutes and had him begging for more. I slowly worked more lube inside then gave him my finger to suck clean.
“This will hurt, some, at first, but the pain goes away,” I warned. “Try to relax.”
Mr. Smith clenched tight as I tried to push into him. I slowly pushed the head into his tight pucker and was rewarded by his yelp and the head popping in!
“Ow, ow, ow, ow!” he cried out. “That hurts!!”
Damn! This felt pretty good to ME!!
“I didn’t cry when you fucked me! And you have a bigger dick!”
He whimpered the whole time I fucked him, and I wasn’t even fucking him hard! I rode his ass, grinding against him for several minutes before I emptied my load into him.
I lay on my back, cock still hard. He licked his lips as he looked at it then started sucking again. He forgot about his sore ass as he sucked me. I would have been content to let him suck me the rest of the evening, but my cock had a taste of his ass and wanted more!
I didn’t bother lubing him as I mounted him doggy style. I grabbed his hips and pulled his fat ass back onto my cock. I thrust hard and deep (for me, anyway) causing him to grunt when my balls slapped his butt. I slapped a cheek every now and then as I rode him to another orgasm.
I sat on the edge of the bed and had him kneel in front of me. He started sucking and licking again. He would have to suck me quite a while, now, to make me come. He really seemed to enjoy sucking my cock.
When I finally filled his mouth with my cream, I pulled his head down to my crotch, forcing him to swallow.
“Do you like my tasty cream?” I purred.
He nodded his head yes as he continued sucking. I pushed him away and raised my legs over my head. I applied a little lube to my asshole and pointed from his cock back to my winking asshole.
“My turn,” I growled. “Fuck me good!”
He crawled on top of me and slid right in. He grunted as he rapidly thrust into me. I’ve been fucked better, but this was still nice. A cock sliding in and out of my chute is a very pleasing sensation! I never seem to be able to get enough cock! That may be why I’m so slutty!
He surprised me and fucked me hard for a good half hour. He was pounding my ass for all it was worth! I was relaxed and enjoying the ride. With one last savage thrust, he filled my ass again.
“Lick me clean and I might give you more of my cream,” I purred. “I want to watch you eat my ass! Pretend you’re eating your wife’s pussy!”
Mr. Smith knelt and licked my ass hole like an ice cream cone. He was lapping all his juices that were leaking out of my ass. He circled my pucker with his raspy tongue, the tip darting in and out. Damn! He ate my ass wonderfully!
I slowly stroked my cock while he lapped at my hole. He watched my hand as he licked an probed my anal opening. I teased him with my show. His tortured expression showed me he was ready to lick my cream from my cock.
I’d teased him for nearly an hour, savoring the rimming I received. I arched my back and covered my stomach with a fresh load of cream. I dipped a little on my finger and let him suck it.
“Does that taste good? Would you like some more?” I teased.
He nodded yes as he continued licking my asshole. I dipped my finger into a little and covered my breasts. I smeared some on my lips. I motioned for him to start licking upwards. He licked and sucked all my cream from my stomach and worked his way to my breasts. I gasped in pleasure when his tongue lightly flicked over my nipples as he continued cleaning me.
When he reached my lips, I grabbed his head and kissed him passionately, then pushed him away.
“Same time next week?” I asked as he walked out my door.