Sissy Donna's New Boyfriend

Craigslist is a waste of time, or so they say. Nothing but flakes. But, I understand that mentality. Society plays a mind fucking game with us girls and some guys who secretly admire us. You put up the ad, and then there's a response. It's gonna happen. Suddenly, you feel shame for even thinking about this, and you cancel without saying anything.

I get so tired of the shame that I almost want a national day of sex with the same gender. Get that gay shame out of the way. Make a guy suck cock. Make a woman eat pussy. Learn and understand. On second thought, I would never force anybody. It's wrong. What I want to do is get people to embrace who they are with pride and be accepted.

My name is Donna. It took me many years to come to terms with the fact that I am transgender. I never had a relationship with anybody. I kept my heart guarded. Nobody could hurt me that way, but it's a lonely path. I recently decided to give up on the notion that a woman would ever want me, and I'm looking for a man who I can be friends with.

Desperation had reared it's ugly head and made me want cock, just for cock's sake. So, I put an ad up on Craigslist. I have a long walk to the grocery store and I drag the bag of groceries back home. It has wheels, but it's annoying. I had hopes of meeting a guy for a ride home and giving him a blowjob in gratitude. I could not anticipate what was about to happen.

I put up the ad and left the house. They would know me when they saw me. If they were interested, they'd just approach me. I let them know my name. I was in the local dollar store trying to pick up what I could for the price. It's hard making it on my own, and I barely get by.

I was pleased with myself, because I had found a lot of nice deals. That meant less money spent at the grocery store. I saw him looking at me as I walked down the canned food aisle. He was a couple inches taller than me, maybe 5 foot 10. He wasn't dressed fancy, but nice. At least it wasn't a t-shirt and jeans. He had brown hair and a beard.

I was grabbing some oatmeal when he approached me. You're not gonna miss me in my red dress and sandals, showing off my red toe nails that match my finger nails. I had on red lipstick and did my eyes in a smokey blue. I'm over dressed for shopping, but I get so few opportunities to dress up these days.

He walked up to me with a smile. "Are you Donna?"

Wow. This was the first response to one of my ads. "Yes, I am."

He looked at my cart. "Are you grocery shopping here?"

I nodded. "I kind of have to. I can't afford to get everything next door. I want to eat, so I am lucky to be able to do this."

He looked at me. "Put it back."

"Huh?"

"Put it back and let's go next door, " he repeated.

I shook my head. "I can't have you doing that. You don't even know me. Just let me finish and..."

He took my hand, and I felt goose bumps from his strong, yet tender touch. "Did I ask you for permission? I want to do this for you, and you don't owe me anything."

I felt a tear in my eye, and I tried to stop myself. I didn't want to ruin my makeup. "Well, maybe just a few things, but not too much."

He started putting things back on the shelves. "You let me worry about that."

At the grocery store, I was looking for the cheaper things, and he wouldn't hear of it. "He grabbed some packs of ground beef and threw them into the cart. I don't eat that much, and now I could fix spaghetti with ground beef again. What he put in my cart was nearly triple what I spend on my groceries, and he bought it all for me.

At his car, I hugged him. "Thank you. I don't even know your name, but thank you so much."

He held me in this embrace, not moving in to try to kiss me. "My name is Paul, and you're welcome Donna. Let's get this home."

Paul was a total gentleman. He stood at the door with a bag of groceries. "Do you mind if I come in?"

I smiled. "Don't be silly. Of course you can. Don't mind the mess. I need to clean more than I have been lately."

With the bags in the kitchen, I insisted he have a seat in the living room and turned on the TV. The game was on. "Have a seat. Would you like a drink? I have soda. I think I have a beer left. Maybe something harder?"

"I don't drink much alcohol, but a stiff drink sounds good, if you'll join me."

"Vodka and Coke okay? I'll join you when I put things away."

He smiled at me. "Sounds great."

I had this bottle of Cake Vodka that I've been keeping unopened for a year. Now seemed like the time to open it. I sat on the couch next to him and we enjoyed a drink. "I hope you don't mind me saying this, Donna, but you have a beautiful body."

I blushed. I'm not the most self confident girl out there. I know I'm no Vaniity or Bailey Jay. "I don't know about that, but thank you."

"Oh listen to you, girl. Just shut up and take the compliment. What I was getting at was I wonder if you have anything sexy you'd like to wear for me. Not that you don't look hot in that dress."

My body felt a tingle at his words. "Well, let me see what I can slip into."

"You do that, " he replied as he held up his empty glass. "And, I'll take another drink if you have it."

"Oh my God. What do I wear, " I asked myself? I had never modeled any of my more than two dozen nighties for a man before. Most of them aren't all that sexy, but I have a few for this occasion.

I slipped out of my clothes and my red bra and panties. I grabbed a red thong and a red nightie. It was satin with just a bit of lace and it was short. My ass would not be hidden by the nightie.

I applied some strawberry body spray and touched up my red lipstick. My makeup was holding up nicely. In front of the mirror, I touched up my hair a bit, took a deep breath and exhaled slowly. "Here goes nothing, " I muttered to myself.

I felt his eyes on me as I walked into the living room and grabbed our glasses to refresh our drinks. "Damn, baby. You do have a nice body. Nice ass too."

I just giggled as I brought the drinks and took my seat next to him. He took a drink and put his arm around me, rubbing his hand on my body and underneath my nightie. He squeezed one of may small, but growing breasts. "Such smooth skin and a nice little handful here."

"Mm, thank you baby, " I heard myself say.

"I hope you don't think bad of me for asking, but as you can see my pants are a little tight..."

I looked at the bulge in his pants and I could only imagine how big his cock might be. "Of course, sweetie. Let me help you with that."

When I got his pants and underwear off, I was shocked at how big his cock was. It was at least eight inches long, not that I had a ruler. This was a different moment than I'd ever been in before. It was the first time I had ever been with a man in such an intimate setting.

I dove down mouth first onto his massive cock. It was a hairy cock, but I think a man with a hairy cock is sexy. Sissies are smooth, men are hairy. As I sucked, he rubbed his hands gently on my back and reached over to squeeze my ass. It made me suck him even harder. I had never been handled this way before.

"God, you have a nice ass, " he said as I deep throated his cock. "Don't stop what you're doing, baby."

When I could taste his cum, I slowed down. I wanted him to cum hard and drink it all down. "You are a sexy girl, Donna. You know that?"

I teased his cock head with my tongue and continued my slow, sensual blowjob. "You're gonna make me cum baby, " he proclaimed as I felt a finger of his pushing against my tight hole.

"Well, maybe you need to cum then sweetie, " I replied as continued sucking his massive cock and gently playing with his balls. "Feed me, baby."

I felt a finger enter my sissy pussy and push in as I tightened around it. "I bet it would be amazing to fuck you, Donna."

I could feel a wetness in the front of my panties. I was dribbling from the excitement, even though I wasn't hard. His finger fucking me only added to the sensation. I could taste his manly juices and decided I needed them down my throat.

Knowing I could easily make it happen, I worked that most sensitive area of his cock with my tongue as I sucked, and he shot a tidal wave of his baby juice into my mouth. I have in the past just swallowed immediately, but I kept it in my mouth and swished it around as much as I could without letting a drop escape. I wanted to savor his taste. That was not an easy task with how much he came.

After a couple moments, I realized he was still finger fucking me as I cleaned the last drops from his cock. "That was amazing Donna. I suppose you'll be wanting me to go now."

Impulsively, I moved up and kissed him. "Does this answer your question, baby?"

He probed my mouth with his tongue. I was bring kissed by a man for the first time as he held me in his arms. I felt secure and happy where I was for the first time in I don't remember how long. I knew what was to come next, and I wanted it. I was gonna let him have my pussy.

Paul continued to be a gentleman. I refilled our drinks again and we watched the game and talked. I was having a good time with him. We laughed a lot. We found that we had a lot in common. When the game ended, he revealed his desires. "What do you say we take our game into overtime, beautiful?"

I kissed him. "I thought you'd never ask."

I took his hand and led him to the bedroom where I sat on the bed as he stood in front of me. I didn't have to suck his massive cock very long. It was already hard. "Baby, why don't you get on your hands and knees at the edge here and let daddy take over."

I did as requested and presented to him. This is such a vulnerable position for a girl to be in. My sissy hole was exposed, and he surprised me by licking it and sticking his tongue inside me. I loved it, and I pushed my tush back in his face as I moaned. "I see somebody wants daddy's cock inside of her, " he said.

"I want you inside me, " I replied. "Fill me up, baby. But, be gentle."

His cock pushed against my hole and I wondered how much it might hurt. "You've never been fucked before, have you?"

"Only with toys , " I replied as I looked back at him.

He smiled and pushed in. "This is no toy, darling. Just relax. I'm gonna make you feel real good."

As the first few inches slid in, it hurt. It wasn't a pain I wasn't used to with my toys, but he showed such concern as I moaned. "Are you okay, Donna? Let me know."

"Mm, I'm fine. Keep going, baby."

"God you are so tight, " he said as he pushed in a few inches more.

"You'll just have to stretch me, " I said through the tolerable pain.

"Fuck, Donna, I forgot the condom, " he said as he stopped pushing.

I pushed back against him. "Just fuck me, Paul. I trust you."

He pushed in further. I don't know if he got all the way inside of me, but I know how full I felt. I looked back at him and was met by him leaning in for a kiss. Being penetrated by a man as he kisses you. Is there anything better? My whole life was leading up to this moment.

He began slowly thrusting in and out as I got more comfortable and the pain gave way to pleasure. There's that moment when you start feeling a distinct pleasure that you can't get from touching your clitty. I have always loved that moment with my toys, but it was even better with a real man.

I didn't just sit there taking his cock. I pushed back and met his thrusts. I wanted him to know how much I was loving this. I was more that just a place for him to put his cock. I wasn't just giving pleasure with my pussy, I was receiving it as well. His thrusts became quicker and deeper, and I loved it. I was being fucked like a real woman. Fucked like the woman I have become. I no longer had any doubts who I was.

"Baby, lay on the bed, " I told him as he pulled out "I want to ride you for a while."

He lay on the bed and I mounted him, taking his cock in much easier this time. I lay down on him and kissed him passionately as he ran his arms around my back in a nice embrace. The two of us had become one in that moment, and his cock was hitting me in a nice spot as my clittly dribbled.

I began riding him up and down as my half hard clitty bounced up and down. There was always something so sexy about watching the t-girl porn stars in the videos as they bounced up and down. For that moment, I felt like a porn star. More than that, I felt like a slut. I had him all the way inside me, and I grinded my ass against him, squeezing him gently inside me.

"Fuck, Donna. Are you sure you've never done this before?"

I smiled and shook my head. "Never. You are the first."

"A guy could get used to this, '" he replied as he pulled me down in another embrace.

Soon, I was on my back with my legs in the air. He had me pinned and was balls deep inside of me. This has always my favorite position to cum with my toys, and I felt that moment approaching. It was immanent, and I resisted the temptation to touch myself. He seemed quite skilled at what he was doing.

"Are you sure you want me to cum inside you Donna, " he asked?

The lyrics from a Rihanna song came to mind just then. "Cum into me, Daddy."

He increased his pace and I started cumming in a slow and steady manner. I could barely keep my eyes open I was in such an orgasmic state. Soon, he thrust in deep and tensed up and unloaded his sperm deep inside me. The feeling was indescribable, but I loved it.

He looked over at the clock and then kissed me. "Shit, I feel like such a jerk, Donna. I gotta get going."

I frowned "Oh. Gotta get back to the wife?" I was mad at myself for letting a married man fuck me, but that wasn't it at all.

"No. I'm single, but I gotta get up for work, " he replied with another kiss before getting up and getting dressed.

I lay on the bed for a moment before getting up and putting on my nightie, panties and a pink robe. "Oh, okay."

I walked with him to his car. "I would like to see you again, Donna, if you want to see me."

"How about Wednesday night for dinner? I'll make spaghetti."

He kissed me and got into his car. "That sounds great. I'll see you then."

His cum was leaking out of me as I watched him drive away. The neighbors may have seen this, but I didn't give a damn. For once in my life, I was truly happy. I never thought a Craigslist ad would go this well. Now I have a boyfriend, and we're already talking about moving in together. I like the idea, but I'm going slow for now.


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