I have been wondering a lot lately about what being taken with a strap on for the first time would be like.  I wonder what position i would be in, and if i would be bound in anyway.  I also am very curious about the sensations both physical and mental that would be experienced.

I am asking the members here who are willing to share their experience the first time they were stretched by a Strap On.

I also humbly ask any Mistress willing to share Her experience taking a sub for the first time.

Thank you all in advance for the input.

subkerin,  thanks for the response.  i will have to male a mental note to make sure there is good footing when i get lucky enough to be in that position :)

My Mistress dugitally explored my virgin pussy hole, first, then used a speculum to further stretch it for the strap on i was to receive.

 As for the position, Mistress had me on my back, with a posture restraint that held my legs up and went around the back of my head. my hands were locked to my legs on the loops provided by the posture device.

This kept me exposed and vulnerable for what She was about to do. I was left there for a short while, but it felt like an eternity.

When She penetrated me, i was in heaven. It was every thing and more that i had fantasised about. She fucked me good and hard and it is how i was allowed to release then eat my own mess. This had all occured towards the end of the session, as a reward for serving Her, as well as to make me her property by breaking me in..

i have also been tied and on all fours, wearing lingerie, for Mistress, before She makes me soak my knickers in pre cum, before reomoving them, stuffing my mouth with them and then taking Her pussy arse with a larger strap on than before. It hurts, but only for an instant, as i am not used to the size, and am expecting the "norm" but i find myself pushing back wanting more, like the slaveslut i am.

ss408

my first time; MISTRESS had used a series of butt plugs from small to medium inside of me throughout the session. When it came time for MISTRESS to take my boy-pussy, it was with a small strap-on 6"x 1"(diameter). i was on my back, with my hands and feet secured to the wall. MISTRESS gently slipped the strap-on inside ofmethen began to pump mefirst slow then eventually SHE was slamming into me. Now, however; MISTRESSES simply lube me,get the head in and then drive the entire shaft home. {Oh by the way, the strap-ons now are a bit Larger}. Saddle up COWGIRL.

Whilst bending over a punishment bench is the fantasy of many, the way that makes it most comfortable for Mistress and far less strain on he back and thighs, is to have me on my back on the punishment couch. My arms are strapped beside me and a broad leather body strap is placed round my chest so I cannot move an inch – with ankle straps fitted, my legs are hoisted in the air and pulled apart, exposing me for her attention.

The first thing I have to endure is watching her getting into her strap on; she usually puts a soft cloth between the leather base of the strap-on and her pubic area… I have been too shy to ask if this is really just for comfort, or to absorb some her dampness, as I know she does certainly get very aroused and flushed in her face and  she cums when it is a really good session..

When she is ready she lubes up with KY, using latex gloves to smear it all over the strap-on, then she squirts a good amount over my hole and with one finger just traces the line that leads from my balls down across my hole and on… She does seem to linger as she crosses my tightly closed pussy hole.. but she never allows it to enter or ‘investigate’ my readiness.

Then she peels off her gloves and clasping her own hands behind her head, she moves forward between my legs and just rests herself, with the tip of the strap-on pressing against my tightly closed hole. She waits and exerts gentle pressure and to begin with nothing happens, but then I suddenly ‘give’ and it slips in just a tiny bit. She stops with it ½’’ in and looks to see my face.. she is looking for the look of fear, as I know what is going to happen.. she lowers her hands, places then round my thighs and then in one movement she thrusts the entire length inside me in one continuous act. She leaves it deep inside for some seconds and then withdraws almost all of it, before plunging it back in again up to the hilt.

Once she is content, she then sets about giving me a proper seeing to, and if she is feeling generous, and her exertions have made her excited enough to cum, she grasps me firmly and allows me to make a white sticky mess all over her hands…

She is the perfect Mistress….

i can't speak for anyone else but i Love it. my first time a finger (s) was used first to lube and open me up untill i could relax a little. then the good stuffing.

the feeling at first was a bit uncomfortable but once i relaxed and opened up/bore down like a BM. then it was like a thousand small cums. instead of a one time big ejaculation as in conventional intercourse for me i ejaculate with every push and pull of the strap on in me. hundreds of small cums that can leave an even bigger ejac mess than normal.

the best though was one time when i had almost a whole hand inside me and She grabbed and stroked my prostate with Her fingers. whew... talk about manipulation.

i'd rather be f33KED THAN F##K.

If She wants to do You. GO FOR IT...

On the day of my deflowering i should have realized something was up.As i delivered  Mistress L's morning coffee L demanded that i put my largest butt plug in and put on my large leather harness.Of course i quickly obeyed, then finished preparing her breakfast. Before she left for work L came to me and put 6 locks on my harness. She laughed as she left saying that would keep everything in place until she got home.L called during the day, gave me more chores,and demanded that i put our bondage horse out in the middle of our play room,have my hood on,and the blindfold and penis gag in place and be on the horse at 6pm. When L arrived home i was waiting, She quickly did up all the bondage straps securing me. Then she told me it was time to escallate our femdom lifestyle. She removed the penis gag, and shoved her new strap-on in my mouth. then she explained that is why she was late as she went shopping for her toy. She removed it from my mouth and re-inserted the penis gag. L said i guess you realise why your butt plug stayed in all day slut, as she moved around behind me. L removed the plug and applied more lube then slowly entered and fucked me until she had an orgasm.