First Strapon Experience

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First Strapon Experience


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Properly preparing for your first time strap on experience is important. You’ve decided that you want to try having your Mistress use a strap on with you or more appropriately on you. You’ve thought about it, talked with her about it and now you are fairly certain that you are ready to experience being fucked by your Mistress with a strap on.
The only problem is, that no matter how much you want it, you aren’t sure how to prepare for it. There are so many ideas and worries running through your head that you aren’t even truly able to enjoy the sweet anticipation of being taken by your beautiful Mistress.
You need some tips on how to prepare for your first strap-on session and that’s what I’m here to give you. A few pointers about your first strap on experience and ways to make it the most pleasurable for you and for your Mistress.
This means a few days to a week before your first time strap on session start getting yourself ready. Your Mistress will supply you with, or instruct you to get a variety of sizes of butt plugs or dildos. None of these will be especially large, not compared to her strap-on anyway, but they will feel big to you.
Though I know if you have already been thinking about this, that you know you like it because you’ve tried various butt plugs and things. So, this should be simple for you. Use lots of lube and take your time. Wear each one and feel it stretching you out. Then move on to the larger size. This is important unless you want it to hurt even more than it inevitably will.
You’ll also need to do some other preparations physically, like don’t eat any solid food for about 2 days before and set up an internal flush so that you are all cleaned up and out for your Mistress. No one wants a problem with that and of course you’ll need to shave all that hair from between the cheeks and around the balls.
Your Mistress will need to see and reach all your parts and we don’t want any mess. This will help you to enjoy yourself as well. And of course bring lots of lube, lots and lots of lube.
This is when you relax and think about it. Allow yourself to remember why you wanted to do this in the first place. Being fucked with a strap-on is what you want, it turns you on and gets you hard. You truly want to have this happen and it was your idea. Your Mistress may have mentioned it, but you got obsessed. You started wanting it more than you wanted anything, needing it and aching for it.
You are here preparing for your first session because of your own choices. You don’t have someone coercing you to do it, your Mistress didn’t coerce you, she simply suggested and maybe even let you look at or touch her strap on, but you are the one who decided this is what you want.
You should spend time thinking about and imagining the moment. You love the thought of being fucked by your Mistress, so watch videos, lay back and imagine it happening. While you are trying out those butt plugs and doing all the physical preparations keep your mind focused on what you are preparing for.
They say that anticipation is sweet and naughty and you’ll ache even more for it when you have to wait. See this as a waiting time for you, where all you can do is anticipate how amazing it will feel when you are being taken by your Mistress.
Finally you want to get your emotions in order and start preparing for how you are going to react emotionally to being fucked. Will you worry that you’re gay now? Will it make you cry or scream?
You know you are worrying about these things and really all you need to know is that just like anything else you love in a fetish you are simply turned on my being used by your Mistress with her strap on. It doesn’t have to mean anything more or less than that. It means only that you are turned on and want to try it.
This is what you’ve been waiting for remember. The sweet anticipation of getting what you’ve been waiting for from your Mistress. You won’t regret it. After all this isn’t the first time for her and you know how good it’s going to feel and while you worry about becoming addicted to it, as you’ve heard can happen…I can promise you there are worse addictions to have. So relax and enjoy it!
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Toys & Masturbation First Strap-on Experience
This hetero male learns how it feels to be a woman.
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I'm not young and inexperienced, by any means. In my early, sexual-awakening days, I had more opportunities than a lot of guys I knew in the area of sex, both alone, and with willing females. I'm not bragging, but I lost my virginity at 15, and there were several girls who met me as virgins and left me knowing how a man satisfies a woman.
One day, I met a girl and settled down. We raised two great kids, sent them off to college & marriage, and discovered anew the rewards of an empty house. Just me, her and the dog & cats.
It was only about a year ago that I began to get urges for anal stimulation while making love. My wife, not used to this, was hesitant to touch me "down there", but eventually helped me discover fulfillment by inserting a finger or two when I'd request it.
A couple of weeks ago, I made a big and scary decision that I'm not getting any younger (I'm not OLD yet, either), and if I wanted to experiment, well now was the time. I visited a shop that had sexual toys of all kinds. On the wall was a box that seemed to reach out to me. It was a "Beginner's Kit", consisting of a strap-on lifelike dildo attached to a wide elastic harness.
The dildo is 8" long and 1 1/2" in circumference, with a nice gradual curve and protruding veins running up the shaft. Inside the head is a vibrating 'egg' with a wired battery-operated remote control that raises and lowers vibrations.
That night, she was feeling rather frisky after her aerobics class, but wanted to take a nice, warm bath before making love. I decided to join her in the tub. We washed each other well, lingering around all the erogenous places, until we were more than ready to head to the bedroom. She pulled the towel off her still-nubile body, exposing her 32Bs to me, while she switched off the light. Instead of joining her immediately, I turned the light back on and announced, "Honey, while you were gone, I was a bad, bad boy."
"What did you do?” she asked with a quizzical look.
I reached down under the bed and brought out the package. I slowly opened the top of the box in the bag, and pulled out the strap-on, still wrapped in plastic.
"You DIDN'T!” she said with a half-assed smile.
"Yes, I did, and I'm going to need your help with it."
She giggled as I helped her step into the harness, the stiff dildo protruding menacingly from her crotch.
"My God, it's so BIG!” she said hoarsely. "It's the same size as you!"
As I helped her adjust it into position, I brushed my hand under the dong and across her smooth pussy lips. She was getting damp and her eyes were beginning to glaze over.
Knowing that things might get 'messy', I took her towel and spread it on the bed. I warned her that there would probably be some 'stuff' on the rubber cock after we finished. She understood, but it didn't seem to matter to her. I reached into the nightstand and retrieved one of my condoms. I unwrapped the foil and began to apply it over the head of the big dildo. A shiver went up my spine as I slowly unrolled it down the length of the shaft to the triangular base, which was fairly secure over her clit and mons. She was right, it WAS big, and I began to have second thoughts if I could take such a large object into my tight little hole. My wife opened her lingerie drawer and brought out a tube of lubricant. Snapping the lid open, she squeezed a generous amount into the palm of her hand. She applied the lube over the head and down and around the shaft carefully.
"It feels like the real thing, Honey," she said proudly. Then looked for a place to wipe off her hand.
"Better use that on me, Darling. I'm going to need plenty of it if your 'cock' is going to fuck me." I said.
I took the position on my elbows and knees on the bed, the towel under me. I rested my chest on the sheet, fully exposing myself to my lover. She wiped her hand over my puckered hole, gently inserting one, then two fingers up my clenched and waiting hole. As she fucked her fingers in and out, I tried to relax as much as possible. She wiggled her fingers in my ass, loosening me up slowly but surely. She kneeled down on the bed and knee-walked up to me. I looked down between my legs, watching the dangling flesh-colored pole sway from side to side as she approached. At first contact with the fake cock, my asshole clenched. I immediately ordered it to relax, concentrating hard to make it so. My dick was stiff and pulsating, begging for release. I reached down to fondle myself as she lined herself up to my butt and pushed the head against my hole. It felt like it would never fit in me, and I again wondered aloud if this was going to happen. She began to tease my hole, gently poking at it several times, until the head began to enter. She gave a big thrust, and the head popped inside me, taking my anal cherry.
I screamed, "Stop, stop! God, you're going to rip me in two!" The pain and pressure was incredible!
"Should I pull it out?" she asked. Before I could reply, she pulled out, doubling the pain but relieving the immense pressure.
"Arrgghh.." I moaned. "Put it back in, but slowly, Sweetheart!"
She pushed the head of the monster back in me. The pain and pressure was immediate.
"OK, STOP! Don't move! PLEASE, don't move," I begged, whimpering into the mattress, tears welling up in my eyes. I finally experienced what all those virgins felt when I poked them for the first time. No wonder they always told me to stop and wait when I got the head in them!
After a few moments to adjust to the intrusion, I felt ready to take more of the cock.
"OK, push in a little more, but only an inch," I instructed. She slowly moved her hips forward, driving the cock into me.
"How much more is there?” I replied.
"About 6 more inches, Honey! God, you look so sexy with my 'cock' up your ass!” she whispered.
"There's no way I can take six more inches of this," I thought. But after a few moments, the pain began to subside, and the pressure began to wane. I purposely clenched my sphincter to gauge if I could stretch to accommodate more. I bore down, as if trying to relieve myself, and found it, too, helped with the pain. I thought I could take more.
"OK, go ahead and give me the rest of that ass-killer," I groaned.
She pushed in slowly, until I thought the head of the monster was coming up my throat. I pushed back toward her, my ass gobbling up inch after awful inch. It seemed to take forever before I finally felt the base against my ass cheeks. My asshole felt bruised and strained, the muscles in my sphincter tight and hard.
"Are you ready to fuck me?” she asked. Not waiting for an answer, she began to pull out. I could feel the fake veins as they pulled across my sore hole. It was both painful and delicious. She slowly pulled out until only the head was inside, and then began to slowly push back into me. On the next few strokes, the pain was subsiding and it was actually beginning to feel good having a giant cock in my ass.
She picked up a rhythm and turned the control on the remote. The vibrations were low and it helped to take my mind away from the diminishing pain.
"I'm not used to being the man," she said. "Is my rhythm OK?"
"Ugh, uh, umm," I replied as she fucked in and out of me. "Yeah, a little faster."
She picked up the pace and turned the vibrator up to full. She was beginning to get a good steady rhythm going, pounding into me like a good man should.
She reached around my waist and began to stroke my now half-flaccid dick. It began to harden in her hand as she simultaneously poked my ass as she stroked. Over and over, she fucked in and out. I could feel each time the head of the dildo pushed across my prostrate gland, and my cock would give an involuntary jerk.
She abandoned my dick as she concentrated on screwing my ass. I reached down and began to stroke myself in earnest as she pounded me.
All too soon, I began to feel the beginnings of an approaching orgasm. Trying to delay it as long as possible, I began to think about what was happening to my slutty ass. Instead of delaying the inevitable, I got more turned on thinking about how it looked to have such a large prick fucking my ass.
"Arrg!” I cried as my jism squirted from my cock. A good six or seven contractions later, and my pecker began to soften. My wife slowed her pumping until she stopped with the dildo deep inside me. When I collapsed on the bed, her cock pulled out of me, leaving me with a deep sense of loss, and a confused mindset.
"Did I really enjoy getting my ass fucked?” I wondered. Yes, I decided, I did. I still didn't want a man to fuck me, but strapping a cock on my wife and letting her invade me was better than just good.
I was physically spent and couldn't move for several minutes. My wife collapsed on me, her big still-hard cockhead pushing into my scrotum. We laid there for several minutes, sweat pouring from her chest on my back, my sweat soaking into the towel beneath me.
Finally, I felt her stir and push herself up. I rolled over as she kneeled between my legs. Grabbing some tissues, I began to wipe the scum from the dildo. My asshole felt bruised, sore and used. I rolled the condom off the hard cock and threw it in the trash.
Retreating to the bathroom, I took a couple of wet wipes and began to gingerly wipe myself off. The mess wasn't as bad as I expected, and cleanup was easy and quick.
When we were adequately clean, I turned on the bath again, intending to take a good long hot soak. My poor ass needed some pampering.
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My girlfriend, Sarah, and I were sitting in bed one night when she started to talk about her friend, Cheryl. We both work long hours at the office, and even though we work in the same building, most of our conversations happen in bed. You know, we ask each other about our days, how horrible our bosses were, everyday couple talk. But I never thought we’d talk about strapon dating .
“Cheryl had strap-on sex last weekend with some guy she met online!” she said with bewilderment.
“Oh yeah?” I replied, my eyes glued to Antman playing on the tv. Man, if I could shrink like that, the first place I’m going is Area 51.
Sarah’s body turned towards mine, demanding my attention. “Yeah, she said it was a little weird at first because she never had to thrust like that before, but it’s apparently a really fun experience.”
I knew where she was going with this. Sure, Cheryl had a good time, but my butt is a no-go zone. What straight guy would allow their ass to get penetrated by a giant dildo?
“Are you sure the guy was straight?” I asked.
“Of course, he was straight. Strap-on sex doesn’t mean you’re gay,” she replied offensively.
I took a deep breath, “is this something you want to try?” I paused in silence, waiting for her answer.
“Well,” she said nervously, “I am really
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