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Here's yet another submission from one of the followers of this blog and All Things CFNM! I actually had this story sitting around on my email address for quite awhile, because I requested the author to try re-formatting it for easier reading. Well, that didn't happen, so I do apologize for it being sort of tough to read. Anyhow, be sure to give your opinion on the content of the story and whether or not it was something you enjoyed!
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A strap on story
I am a male aged 49 and something amazing happened to me the other day, which I would like to share with others.
I have been a secret crossdresser for some 5 years but never gone out, but liked to dress in private and be on webcam etc. By crossdresser I mean I like to wear "kinky clothes such as short mini dresses, short skirts, high heels, sexy lingerie, think you get my meaning.
Anyway some 3 years ago I got married and like many others could not have the courage to tell my partner that I liked to CD, so for the last 2 years I have only been able to "dress" etc at work when everyone else has gone home.
One night at around 5pm everyone else had gone home so out came my box of tricks. I decided that night to wear my shoulder length brown wig, short mini skirt (just covers my bum), white blouse, white socks, tiny thong, and my high heels. I like to take pictures of myself using the self-timer control on the camera and it gives me great pleasure to do this.
Anyway, I was in the main office doing my posing, for example bending over the desk so that my bum was showing, and as usual was getting quite aroused.
I was at the stage where I had removed my skirt and top and was just wearing my bra, thong and high heels, when I heard the front door open.
Now when I am on my own I always made sure that the secondary internal door was locked "just in case" but for some reason I had not done so on this occasion.
The next thing I know is that Joan who works in the administration office walks into the main office where I am standing "helpless". To say she was shocked was an understatement
She cried out "oh my god is that you Rob"? I, feeling very exposed and now frightened stood there and just said "yes" in a very weepish voice.
Joan then said "god Rob this was the last thing I would have expected about you, have you been doing this long"? I then told her all, there was no point in trying to deny things to her
After I had "opened up" to her she said that she had no problems with it at all, everyone to their own and if what I did gave me pleasure and I was not hurting anyone then there was no harm in it.
She then said that I was not to worry, as she would not inform the other staff about this and that it would be our secret.
She then went on to say that, as we are being open with each other, she wanted to get things off her chest as well. She then went on to say that her husband of some 30 years had stopped making love to her a few years ago and that sometimes she gets very frustrated, but as the months had progressed, she had got used to it. Joan is a lady of 55 but looks very much younger and keeps fit by playing tennis two or three times a week.
I felt sorry for Joan and if I was honest I had fantasised about being with her on many occasions.
Anyway I decide to take the bull by the horns and I said" well Joan you know where I am if you want to feel "wanted" anytime". She then said "do you mean it Rob, you actually quite fancy me"? I then said of course I do and as you appear to know everything about me I feel that there should not be anymore secrets between us. She then came up to me and kissed me on my lips and said thank you, it means allot.
We sat and chatted for a while, me still only in my high heels, bra and thong and then she said "well I had better get back off home, but Rob I was wondering if I could ask you something". I replied Joan, ask me anything
She then said that her husband was going away for a the weekend on a golfing trip and that her daughter and son were off to a friends party and staying the night, so that she would be on her own. I saw her gulp a little but she then went on and said "do you think you could come around Friday night? only of course if you wanted too, no pressure. No pressure indeed! I said of course I would come around. She then said "Rob, can I ask that you bring all your girlie things with you, as I would love to see you all dressed up, as seeing you like this has turned me on so much.
I was very pleased to hear her say that and said yes no problem.
A few days later and after each day giving each other winks and nods during the day in the office, it was Friday. I had already told my partner that I was off on a working trip the weekend, so was now free to see "Joan"
Joan had left the office at 3pm like she always did and at 5 it was my time to leave as well. I first phoned Joan to ensure that everything was still ok and she said yes and could not wait to see me.
I arrived at the house and was greeted by Joan at the door. We kissed and I was led into the front room where tea and biscuits were provided.
We just sat and chatted about everything for ages and ages, it just felt so casual and friendly and before we knew it, it was already 8 o'clock
She then asked if I wanted to "freshen up" in the bathroom and I said that would be lovely. She provided clean towels for me and showed me to the shower room and left me there. Before she left she asked that when I came back downstairs could I be dressed as "Roberta" (my girlie name)
I said of course I would and she said great, as I have a little surprise for you when you come back down.
This very much got me going I can tell you, just thinking about what the surprise would be; I lathered myself up and had the biggest erection I have had for a long time, as I washed.
After coming out of the shower, I was drying myself with the towel and thought I heard the front door open and the sound of some talking. I never gave it another thought, as it was perhaps Joan opening the door to a delivery boy or something.
After drying myself, I shaved, but decided not to shave downstairs as I quite liked my "bush" down there.
I applied some make up etc and put on my brown shoulder length wig, then my bra (with suitable fillers), tiny thong. I decided this time not to put on stockings and suspender belt on and but to wear my very very short black mini dress and finally my high-heeled shoes.
I felt so sexy and took one last look in the mirror before leaving the bathroom. As I did I shouted down to Joan "are you ready for me Joan" and she shouted back with a giggling sounding voice "yes of course I am"
I went down the stairs and opened the door to her front room and walked in. As I walked in my mouth dropped to the floor and my heart fluttered so much I thought I was going to faint.
You see in the room it was not just Joan there, there were 5 other ladies present as well, which I could not understand and my initial thoughts were that Joan had double crossed me and wanted to teach me a lesson for being such a pervert – I could not have been further from the truth.
As I walked in she promptly came up to me and said "don’t worry Rob, nothings the matter its fine really, we are all here to enjoy ourselves – hopefully.
She then led me into the front room and said why don't I stand in the middle of the room so that we can all see you.
Sitting on the sofa were 3 ladies who Joan introduced me too, who were Chrissy (aged 48), Tracy (aged 44) and Carol (52). They each smiled and said hello. Sitting on each of the two armchairs were another two ladies one being Ann who was 42 and the other being Kathy (aged 49)
There all looked so friendly and had lovely smiles and they appeared all to be giggling too for some reason.
Joan then said that they all had been friends for a long long time and did have girlie nights quite often, which sometimes did include Ann Summer parties where they each got to try the various toys etc out with each other.
She then explained to me that after her seeing me the other night, she could not contain her excitement about it and so phoned them individually throughout the next day. She said that they all, without exception, found it such a turn on and said that they would love to have the chance to see me for themselves as well and she thought that this would be an ideal opportunity. Joan did say that she was a little bit afraid that I would take it the wrong way and be scared off. I said to Joan that I was not scared at all and in fact I was honoured that they all wanted to see me as Roberta.
Joan then asked me to sit down, which I did on the spare chair available. Joan then looked at the others and then to me and said that there was something else that they wanted to ask, but again they were a bit wary of my response. Well I said ask away as I am honest as well and if you don’t ask in this life you never get.
Joan then said that for ages and ages during their girlie nights they had always said how good would it be to see a man dressed up as a woman and then to perform for them.
For them to be in total control and for him to do as they please, with finally getting the chance to wear and use their strapon's on him until each of them had had their fill.
Joan then went on to say that they had all in the past brought a strapon during these Ann Summer parties but each of them despite wanting to use them so much, had never had the courage to ask their partners if they could use them on them. So Joan said that she thought maybe she had found such a person to act out their fantasy at last. I just sat there taking it all in. I was shocked a little and started shaking not with trepidation but with excitement. Joan noticed that I was shaking a little and looked a bit worried that perhaps she had got the wrong impression after all.
She then said "Rob, I do understand that this is probably a shock to you and with five of us here that you were only expecting to be with me tonight". So please do not feel bad if this is not want you want and we would not be offended if you went and left, there would be no hard feelings ok"
I sat there still dumfounded, then Joan said "ok Rob, we understand if you want to leave, go back to the bedroom and get dressed and we will not say anymore about it ok and please don't feel bad, its ok really".
With that I decided that my mind was made up and got up from the chair and started walking to the front room door. I put my hand on the door handle and turned around to see all five ladies looking at me with sorrowful and worried eyes. I heard them gasp for breath as they saw my hand on the door handle and then Joan let out a squeal as she saw me push the door shut, turned around and smiled at them all. I smiled at them and said "take me as you want, I am here for your pleasure to do as you want with me".
Joan immediately came up to me, kissed me hard on the lips and turned to the others and said "we have found him at last, can you believe it girls"
The others came up to me and all kissed me hard one by one, it was amazing.
Joan then said that she would be in charge for the evening, which we all agreed on.
She then said "right Roberta, please stand in the middle of the room for us will you and do a twirl for us" I did as I was told. She then asked for me to come up to each one of them so that they could feel my curves etc and get a closer look at what I had to offer. I went up to Ann first and stood before her, my mini dress just covering my bum. I felt her hands run up each of my legs and I started to tremble a little. She then let her hands run over my buttocks, squeezing as she caressed them. She said how good I felt and gave me a little wink as she said that she could see that I was somewhat aroused as well. I then went to Tracy who did the same but did let her hand wonder over my crouch, which made me squirm a little. Then it was Carol's turn, then Chrissy and finally Joan
Joan, did as the others but then asked me to turn around which I did and then I felt my mini dress slide up over my buttocks and I heard Joan say "well girls what do you think of this ass then" and gave my buttocks a little slap. The others all said how lovely it was and that they could not wait to see what it could take for them.
Joan then pulled the dress down back and said that she wanted me to dance for them. She went to the music player and put on some dance club music, which I danced to, flaunting myself to the music and on occasions lifting the dress again over my bum and wiggling it about for them.
After the music had finished Joan then said that she wanted me to remove the my dress, so that all I was wearing would be my high heeled shoes, tiny thong and bra. I did as I was told and then stood before them. I could feel my erection trying to get out from the tiny thong, but to no avail, but on the other hand it felt bloody good as well.
Joan then said that they were now going to go out of the room for a few mins, but for me to make myself at home sit down and relax until they came back.
I saw them leave the room one after the other, still giggling away to each other and I sat down and tried to relax, without success, I so wanted to cum already!
After what seemed like ages, I heard footsteps coming down the stairs. Joan was the first to enter the room, then the others followed. The sight I saw will live with me for the rest of my days, it made me even more hornier, but also made me gulp a little as well
All the ladies were now wearing their individual strapons. All the ladies were now topless and had their boobs showing, some large, some smaller but all very very likeable that’s for sure. They were all wearing high-heeled shoes as well but nothing else besides the strapons.
Joan asked them to line up in front of me and then said to me "Well Rob, do you think you can handle these, please say if you don’t think you can we would all understand" I looked at each one of them.
I looked into their eyes and I could see that they were all turned on so much. I turned to Joan and just said "do as you want with me" They all nearly collapsed with excitement and both Ann and Tracy even let out a little squeal and said that they had just cum already.
Joan by far had the largest dildo, around 10" but the others ranged from 6" – 8" and I knew I was in for a pounding, but at that stage I could not have cared, I was just in a sexual frenzy now.
Joan then said for me to come up to her and kneel before her, which I did. She then offered her dildo to my mouth and said for me to suck it nicely for her. I eagerly did as I was told, running my tongue over the very long shaft and then taking the head in my mouth. I could feel Joan pushing forward, which at first made me gag a little, but I soon got used to the sensation and took more and more with each thrust forward.
The other ladies were waiting patiently and then Joan withdrew and Ann was the next to place her dildo at my mouth and again I sucked very hard. Ann got a little carried away and thrust very forcibly which made the dildo push my cheeks out. Tracy, Carol and then Chrissy all followed and after my mouth was somewhat sore from all the deep thrusting that had taken place.
Joan then asked if I liked that, which I replied somewhat sheeperly that I did. She then said that all the ladies were so turned on now and that they all had very wet pussies.
Joan, with Ann, Tracy and Carol left the room, which just left Chrissy and me. Chrissy began to chat and said that this scenario had been her ultimate fantasy and having someone as sexy as me was a bonus, which made me feel "special". I could see that her nipples were so hard so I asked if I could suck them. She said of course and bent down a little to enable my mouth to enclose around the nipple. Wow it was hard and as I was sucking I did reach under and felt her pussy, which I must say, was absolutely soaking.
Then there was a bang against the front room door and I looked round and saw Joan, Ann, Tracy and Carol bringing in a solid looking table which was about 3' high off the ground.
They placed the table in the middle of the room and at first I did not know why they had brought such an object in.
Then Joan said to me "ok Rob, can you climb up onto the table for us". I did as I was told and was just about to stand up on the table when Joan said "No Rob, please don’t stand up, will you please go onto your knees for us and pose in the doggie position". The penny then dropped and I knew then what I was in for. I went into the doggie position on the table. Joan asked me to shuffle back a little so that my feet dangled over the edge.
My cock by now was very hard and I could feel the pre cum oozing from it. Ann looked at my eyes and then at my cock and she said "look girls his thong is wet, I do believe he has pre cum".
They all then looked and Joan even reached over and gave my thong a gently caress, which made my situation even worse!!
Joan then said "Right ladies, this is the moment I think we have all waited for, lets see what Rob can take eh. Are you ready Rob you don’t want to back out?" The words could not come out of my mouth, but I just nodded.
Again Joan took control and said "ok ladies we will be doing this one at a time, to start with" This startled me, what did she mean one at a time TO START WITH?
Joan then asked Chrissy and Carol to go around the front on the table. Joan then asked for them to grab one of my hands each and to take a firm grip so that I couldn't move them. This they did and when they did I could instantly feel that they were indeed strong ladies.
Joan then went behind me and then I felt her hands reach under the sides of my thong and then felt the thong slowly being pulled down over my bum. She asked me to spread my legs a little for her, which I did and then she asked me to lift each foot up off the table, for the left one then the right one, so as to remove the thong fully. I felt VERY exposed now and could even feel the slight wind coming from the open window, breezing up my anal hole.
I then saw Joan again and she had a tube of lubrication in her hand now and then poured some of the slippery liquid into her hands and over her fingers.
Again she then stood behind me and I heard her say "ladies, we must always ensure that Rob is well lubricated as if he does "dry out" the experience can be painful"
I then felt the cold liquid being rubbed over my buttocks, over my hole and even under between my legs, balls and cock. There appeared to be loads of the stuff and then I felt a finger slide inside, then two then three. Joan said, "that’s a good boy Rob, come on expose yourself for us, just a little bit more. Arghh that’s it" .Well ladies I do believe I subject is now ready"
Ann I think we will start with you is that ok. I looked up and saw Ann with such a big grin on her face.
Joan moved to the right hand side of the table and I saw Tracy move to the left-hand side. I then felt both of them lean down on each side of my bum cheeks, so that I was not able to move at all. What with my hands being held down and now my side / bum as well.
Ann, whose dildo was about 6", placed the tip at my anal hole. I felt it at my entrance and braced myself for what was to come.
Although Ann had said she had never done this before, she started off so slowly and ensured that I was as comfortable as possible.
I felt the didlo slide in by about 2" then I felt it slide back out. Joan said, "that’s it Ann take it slowly at first, but perhaps go a little deeper with your next few thrusts"
I felt Ann push forward again. My hands gripped the hands holding me down and I took a gulp. I felt warmness inside my anal hole and a little bit of pain, but nothing horrible.
Ann started to thrust deeper and deeper now and stated to go a little faster. I could feel both Joan and Tracy holding my bum still and ensuring that the dildo was entering at the right angle.
Then all of a sudden Ann said, "oh my god, the dildo has gone all the way in, is this right" Joan said yes that I had now become fully open. Joan then said that she was now free to start slamming into me
Ann then stated to pump me faster and faster. I could feel the table start to shake a little, but I was stuck fast. My bum was now taking a serious pounding but by god it felt so good, I even felt myself trying to push backwards with each of Ann's forward thrusts.
After what seemed only a short while, Joan said to Ann that she should now let Carol have a go. I felt Carol lose her grip on my hand, but was replaced almost immediately by Ann's.
There was no starting slowly with Carol, who's dildo measured slightly bigger at 7" I felt it go in straight away and she thrust forward into my gaping hole. She made noises as if she herself was cumming.
Then she pulled out and Chrissy took over, then Tracy, whose dildo did stretch me, as it was some 8".
Then it was Joan's turn, the lady who I slightly feared most. I looked up and saw her walking around the table, the dong looked massive, as it was being 10" or more.
Joan came up to me and placed the dong at my mouth and said "ok Rob, this is the monster one, you are now going to be stretched the most you have ever been".
The others all shouted, "yeah, lets see if he can take that eh"?
Joan rubbed plenty and I mean plenty of lube over the dong and also into and around my bum
Then I felt it at my entrance, god it felt so big. Joan pushed forward and as she did she said, "girls please ensure that you hold him down as he may try to struggle out of this, but this has now gone too far and even if he doesn't want it, he is now bloody well going to get it"
With that I felt all the ladies grip grow tighter around me
Joan eased the dildo in, little by little. I squealed in pain as it felt so big, but my squeals fell on deaf ears as I felt it go further in.
Joan did reach under and started to masturbate my cock but then I felt the dildo go in deeper and all of a sudden the pain drifted away and excitement started to build up inside me.
I found myself saying, "deeper Joan, deeper", the girls were all smiling and encouraged Joan to thrust deeper. I felt my hole expand and was now being pounded so much by this giant dong.
I could hear Joan saying oh my god girls its going in further and further, oh my god oh my god" I heard her cry out and I knew then that she had just cum herself. Then there was another push and I then heard Joan say "oh ladies, it's gone all the way in, can you believe this, he has actually taken the whole thing"
I must admit I did feel "full" and was starting to shake now with all the pounding I had been given.
Joan then offered the others to have another go and they did one after the other and more forcibly this time as well, but it felt so good
After a good hour or so of this Joan then said "ok girls, shall we see what we can do next with him"
They all replied oh yes.
Joan then said for me to get off the table, which I did.
She then got Chrissy who had the smallest dildo at 6" to relax on the sofa with her legs over the edge but her feet flat on the ground. In this position her dildo was sticking in the upright position.
Joan then told me to sit astride Chrissy, facing her and ride her dildo in this position. I did as I was ordered and began riding the dildo.
After a while I then felt Joan and Carol's hands on me and pushed me forward so that I was virtually face to face with Chrissy, our lips almost kissing.
I still had the dildo inside me, but then I heard Joan say to Ann, ok Ann see if he can take it
I then felt another dildo trying to gain access to my hole and then realised what was happening.
They wanted to see two dildos in one hole and boy were they going to get it as well
The pain was excruciating at first, but then I felt the two dongs side by side inside me, riding me for all their worth.
I was shaking so much and felt as if I was gong to faint, but the others kept me upright and straight
After some time they both eased out and everyone shouted with excitement, it had lived up to all their expectations and more.
Joan agreed with them and said that it had been great but perhaps they should give Rob a reward for being so good – they all agreed.
They then all removed their dildos and asked me to lay on the floor. I did as I was told and then one by one they sat astride my face and ordered me to give their pussies a good licking. God, each one tasted absolutely fantastic and I am proud to say that I made each girl cum and I was able to taste their juices.
Finally it was over, but Joan said that there was just one last thing.
She got me to sit on the sofa again in the relaxing position, with my feet flat on the floor
Joan said to me that another one of her own fantasies was to masturbate a man but to then make sure that when he cum's he shoots into a small vessel so as to collect the cum. Then she says that her fantasy is to then tell the man to drink it all up for her.
I was somewhat shocked about this fantasy but was in no mood to say no as I was desperate to cum. The other ladies all said that they had not thought about this before but after Joan had said, they were very much looking forward to seeing it done.
Joan looked into my eyes and asked me is that ok then? I just nodded; well what could I say I was lyaing there with an erect cock, which was needing a seeing too.
The others sat around me whilst Joan knelt on the floor between my legs. She had brought with her from the kitchen a small plastic cup.
She looked up at me and asked if I was ready, for which I replied yes.
She started by ticking the underside of my balls, teasing them as she did. My cock sprang up even more and I thought I was going to cum straight away.
She then said to me that she was just going to rub the top a little with the foreskin still over the head
I saw her thumb and index finger wrap around my cock and gently felt the rubbing sensation over the head and saw her hands moving up and down but making sure that the foreskin remained over the head – god it felt good.
She looked up and said that my cock felt good in her hands and that she could feel it twitching now and again
She then caressed my full balls, cupping them in the palm of her hand and then gently squeezing them.
Joan looked at me and I saw her licking her lips which made me feel dam good I can tell you. She then said to me "Rob, I am now going to pull the foreskin right down over the head and as far as it will go down your shaft ok" I nodded to her and then she said "Rob, as you feel me pushing down, would you raise your bum off the sofa and push upwards for me. This will help the foreskin slide over the head and then down the shaft"
Again I nodded; I was in "heaven". Joan then said "right Rob on the count of 3 I will push down and you to push up ok" 1 2 and 3.with that I pushed upwards and felt the foreskin slide over the head and down the shaft, it felt tight but god it was amazing. I could feel Joan's hand pushing down. The other let out a small gasp as they saw my exposed cock head all glistening with pre cum etc.
Joan kept hold of the shaft at the base and again she said she could feel the cock twitching.
I then felt Joan's hand go upward again and looked down and saw the head again covered by the foreskin. She then again started to rub the tip of my cock through the foreskin, with the others eagerly looking on
Joan said to the others "I think Rob is nearly ready for us girls" and I said god yes I am
Joan again looked at me and said "ok Rob I am now going to pull the foreskin back down and then I am going to masturbate you quite quickly. You will feel my hands rubbing up and down your shaft and just cum for us when you are ready ok"
My inner feelings were now all over the place, the tension within my balls and cock was straining so much now. I then began to feel Joan start to pump my cock and in no time at all I felt the foreskin again slide over the head. I felt Joan masturbating me now using her right hand, but could also now feel her cupping my balls in her left hand and she started to squeeze them and pull them downward, which made my cock even more erect.
I began to buck upwards which each of her downward pulls on my cock and I felt saliva start to build up in my mouth and knew I would not last much longer
Joan's hand started to rub faster now and it felt so good looking around me and seeing 5 pairs of ladies eyes looking at me. Joan said to me "nearly ready Rob?" an I said yes yes yes and then looked down and saw her pull my cock in the horizontal position and then place the plastic cup in front of the head.
She kept masturbating me and I could feel the arousal getting even more intense. Joan gave me some encouragement (which I didn't need really) but said "cum for us Rob, we want to see your cum spurt out" Her hands were so expert at this masturbating lark and I then said "oh god Joan, I'm going to cum, I'm going to cum" Joan said "yes baby that’s it cum for us now" With that she pulled down so hard on my shaft and with that I felt the first spurt of cum shoot out from the head. The ladies all said oh yes Rob, oh wow" as I kept spurting my cum into the plastic cup, wave after wave of fantastic sensation was going through my whole body. I heard Joan say, "oh my god there is loads girls"
My body arched upwards as I spurted more until I felt relived and that my balls were finally empty
Joan kept masturbating my cock ensuring that every little drop was out from my cock
I opened my eyes after the sensation had died down and looked up to the girls who all had great big smiles on their faces.
Joan looked at me and then said "that was so lovely Rob and now will you drink your own cum for us please"
She placed the cup by my lips and raised the cup upwards so that my cum slowly dripped out of the cup and into my mouth. I had never tasted my own cum before but I must say it tasted ok, which I was surprised about. Joan made sure that every last drop was out of the cup and then said that that was absolutely amazing, and all the others said the same as well.
We all got up and had a group hug whilst standing in the middle of the room. EVERYONE and I mean everyone said how enjoyable this experience had been. All those pent up fantasies had now come true once and for all and it lived up to the anticipation and MORE so.
I walked out of the room and have to say that my bum did feel somewhat sore but the memories of what just had happened overtook any pain I was feeling..I FELT BLOODY GOOD I can tell you.
I came down the stairs all dressed and walked into the room and saw the ladies had all got dressed as well and looking at us all you would not think how kinky and naughty we had all been just a few mins ago
One by one the ladies came up to me and gave me a hug and a French kiss and saying thank you for an amazing experience. All I said to them was that if they felt amazed then I was twice as much pleased as they were.
With that I said my goodbyes and walked out of the door to my awaiting car. I looked back and saw Joan standing at the door and as I was getting into my car she shouted, "let us know when we can do this again ok" I looked at her, smiled and said, "no problem will do"
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Posted by ATCFNM at 6:21 PM