My Strapon Fantasy

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A girl helps her boyfriend live out his fantasy.
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I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her.

I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted to wear tights but I didn't want anything to get in the way later. Luckily, after some digging I found some hold ups in another draw. I put on a short black skirt and a red top and went to get on with my day.

A little while later, I could hear her coming through the front door. I ran to meet her and immediately assumed my role for the next few hours. You see I'm usually the dominant one in the relationship but today my girlfriend had promised to take over and I'd be totally passive. So here I stood in the hallway, my arms around her neck kissing her with her hands casually falling to my ass.

As I'd grown up, I'd lost interest in crossdressing and much of my old submissive side. In fact, as I already mentioned I'd grown to love being in control during sex but there was one fantasy I couldn't forget. For years I'd wanted to be fucked by a hot girl with strapon, even better if I was dressed as a girl at the same time. This was what Amy had promised me today.

I went to make her a drink and she sat down watching my ass. I brought her the drink and sat sideways on her lap, legs together. She kissed me again, her tongue pushing its way past my lips and I held on to her eagerly kissing her back. She pulled me further up her leg and I could feel a large lump in her crotch. She ran her hand up my thigh, teasing my ass, playing with my thong, running her hand across my now rock hard cock and altogether driving me insane. She pulled off her shirt and pulled my head down. I kissed down her neck to her chest and then moving her bra to the side I took her nipple into my mouth, gently sucking it. I heard her moan and bit down gently. She had one hand on my head, grasping my hair and holding me in place, the other was caressing my ass.

"Open my jeans sweetie," I can hear Amy whisper in my ear "I have a surprise for you."

Without leaving her nipple, I unbutton her jeans and pull out her long, hard plastic cock.

"Wrap your hand around it Sissy, I want to see your painted nails on my cock. The same way you always enjoy looking at mine."

She moves my head and I start sucking her other nipple, whilst she watches me stroke her cock. She was moaning and had pulled my skirt up, running a finger along my thong putting just a little pressure on my ass hole.

"Oh, that's good. Do you like my new cock? I bought it yesterday after I told you how special I planned to make today for you. And best of all, every time you stroke it like th-ah-at, it moves another dildo in me that feels incredible."

"Ok now stand up and take off that skirt, I want to see your ass"

I stood in front of her and unzipped the skirt, it fell to my ankles and I turned round so she could see my ass before I sat next to her. She showed me how to slide my hand under the strapon harness so I could tease her clit and then pulled me so I was half on top of her. We start to kiss and I rubbed her clit, building her up further after stroking her cock. I could feel her hand on my ass, she moved my thong to the side and gently pressed against my ass hole. I gasped as I felt her finger slide in and started slightly thrusting my hips; I never could help myself when she fingers me. We moaned into each others' mouths as we fingered each other and bizarrely, I stroked HER cock. She pushed another finger into me and it sent me to the next level, I rocked my hips on her two fingers just imaging what her cock would feel like. Just as I really started enjoying her fingering me, she pushes me onto the floor.

"Well Sissy, you've been on the other side of this a few times." Amy was looking at me, smiling as I knelt on the floor between her legs. "So I'm sure you know exactly what to do."

I moved between her legs and gave her the kind of blowjob I love her giving me. I stayed fairly far from her so I had to lean forward to take her cock in my mouth. I was on my hands and knees between her legs and I pushed my ass up as high as I could, looking up at Amy with her cock between my lips. I'd lost my shirt so I was just in my purple thong, bra and black hold ups, in our usual roles this sight is enough to make me cum and I loved the thought that maybe she was enjoying it just as much.

I held the base of her cock, stroking it and then lowered my head, taking the cock in my mouth as far as I could before coming back up. Each time I came to the top of her cock, I looked up at her licking the tip of simply pausing with the head in my mouth before continuing. She was moaning at the sight and the way it was moving the dildo inside her.

"You're a natural Sissy..." She stroked my hair. "...but that's not exactly what I'm after"

She knocked my hand away and grabbed her cock at the base, her other hand was on the back of my head gripping my hair and she started to push me down. She was thrusting her hips and forcing her cock down my throat.

"Oh that's incredible Sissy, no wonder you love doing this to me"

I kept gagging so she'd pause to let me breathe before fucking my mouth again. I loved being used this way. I was rocking back and forth from the force of her pulling me onto her cock and my hips were thrusting as I imagined what it would be like when she was actually fucking me.

"Wiggle that ass for me Sissy, show me how much of a slut you are. I'm abusing your mouth and all you can think is how you want me inside you. Well you're nearly in luck Sissy."

She pushed me off her and lay on the floor. She told me to come over to her and get on top of her so she could eat my ass as well as have me suck the strapon. I took the strapon back into my mouth, and slid my hand under the harness to I could tease her clit too. I felt exposed when my thong was moved to the side but then I her tongue touched my ass and I shuddered. It was so so good. I sucked her strapon eagerly, spurred on by her tongue in my ass.

"Does sissy like his ass being eaten?"

"God yes, it feels incredible"

She laughed and pushed her tongue further into me, fucking me with it. She hadn't touched my cock this whole time but I was so on edge from everything that it didn't matter. I was desperate for her to rub my cock just a little, I really wanted to cum.

"Please, please play with my cock!" I begged her.

"Hmm Sissy, it should be my cock you're worried about today!"

She had me stay in place and got out from under me. I was now on my hands and knees on the floor my head resting on the sofa with Amy behind me. SLAP! SLAP! She spanked my ass hard once on each cheek.

"Understood?"

"Yes Amy"

She knelt behind be and continued to lick my ass, the tongue circling around teasing me before she pushed it in. Regardless of what had been said before, she reached up and rubbed my crotch with her open hand. I loved it when did that, her hand just cupping my balls and rubbing my cock. It always feels great when I'm in panties but with her tongue inside me it felt amazing.

"Are you ready Sissy?" She was kneeling up now but still rubbing me through my thong.

"Yes yes please Amy."

"What do you want?"

"Please fuck me, please fuck me hard with your strapon Amy."

"I always knew you were a slut"

She was on one knee to give her extra leverage and holding my thong to the side she grabbed some lube from the side and put it on my ass and all over her cock. She then placed the tip against me and with one hand holding her cock and the other holding my hip she pushed it inside. She'd fucked me with things before so it went in easily but the fact it was a strapon made everything feel so much better than normal. She had both hands holding my hips and once her cock was all the way in she really started fucking me. I was moaning and pushing my ass back onto her cock, I loved it and she was really getting into. She grabbed the back of my head with one hand, pulling my hair.

"How does it feel getting fucked by your own girlfriend?"

"Amazing!"

"Haha, I knew you'd love it but I didn't think I'd be getting so much out of it."

She moaned and slammed her cock into me, moving her hand from my head to play reach into my bra and play with my nipples.

"God it feels so good to be on this end of things, keeping pushing that ass back Sissy, you look so cute"

I lowered my head to the floor and pushed my ass right up and back against her as she fucked me hard. I was in heaven; it felt so good to be being fucked by her. She'd pull my hair, slap my ass and pinch my nipples and I'd just moan and move my hips faster. I could hear her breathing change as if she was just about to cum and then her cock left me.

She went to sit on the sofa and just looked at me stroking her cock with her legs wide until I got up and walked to her. I sat straddling her and kissed her, feeling her strapon pressing up against my ass.

"Look at me Sissy, look at me whilst you put my cock back in you"

Looking my girlfriend in the eye, I held onto her cock and placed it against my ass. She had her hand down the harness playing with her clit as she watched me slowly sit on her cock. She moved both hands on to my ass once I had her strapon all the way inside me and took my nipple in her mouth. I bounced up and down on her plastic cock, she thrust it into me and sucked my nipples continually. Her breathing grew faster and faster as she fucked me. It was so hot watching her building up to cum from fucking me. I moved up and down on her faster, realising that I was going crazy from all the fun. She smiled and looked at me.

"Do you want to cum?"

"Yes please!"

"You're going to cum in your panties with your girlfriend fucking you?"

"Oh God yes Amy"

She laughed again and fucked me hard. Her cock was moving in and out of me rapidly and she used one hand to rub my cock through my panties. I could barely breathe from the intense feelings I needed to cum and knew it wouldn't be long. She wasn't far off either; I could tell she would cum any minute. When she was ready, she bit down on my nipple and slammed her cock into me. I erupted, all the build up made me cum more than I ever had before, my stomach, my panties and her chest were covered in it. She saw me cumming on her cock and moaning and that and the dildo inside her made her cum hard too. I collapsed onto her and we lay panting and exhausted covered in cum.

"Thank you" I said and kissed her.

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24 Comments
AnonymousAnonymousabout 2 months ago

Really wish that was me getting fucked by her!

Doc333Doc333almost 4 years ago
great story

this is a great story would love for my wife to do this to me

AnonymousAnonymousalmost 6 years ago
I like the concept.

I am so eager for a big strapon fuck.

AnonymousAnonymousabout 6 years ago
Almost my story

I was introduced to getting buttfucked by my second wife [how did she know] I guess it just shows.I had been bi since the age of 10 or 11 and sucked off most of the boys in the neighborhood.I went from cruising to bath houses to gay bars as a young man crossdressing became second nature but always in secret.She lured me in with great blow jobs and copious amounts of blow next thing you know I'm down on my knees skirt, nylons,and hot red lipstick sucking her cock begging to get buttfucked.You see I never knew what a whore I could be, she did.She talked about turning me out which really turned me on but didn't seem viable, not that I wouldn't do it.She passed 20 years ago this Nov. I loved her very much.Ive had craigs list hook ups once when a guy showed up in drag I asked if he minded if I wore a teddy once a whore always a whore.

DianeRedfernDianeRedfernover 8 years ago
Felt every push and loved every second of it

I love this story and I felt it. The second person technique you use is one of the best I've read. In fact, it seems you know a lot about technique. You and amy can visit me any time.

Hugs & Kisses, xoxoxo, Di!

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