Ladyboys Moving to Thailand and my first Ladyboy
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From Boy To ManChapter 4 free porn video
After Sunday Divisions, I remained in my best uniform and was up ready to fall in five minutes before Liberty Men was piped. I saw Jock and Peter, but the only PO Boy I saw was the one reporting the boys were ready for inspection. It was a formality that an Officer of the Watch inspects the boys before leaving the establishment, or 'Going ashore' as it is called in the Navy. The one privilege of a PO and Leading Boy was that they weren't inspected and allowed to continue out the gate first.
As we made for the small side gate the PO Boy who reported the Liberty Men, grabbed me by the arm. "Are you Frank Bourne?"
"Yea, that's me."
"I'm Sam Stubbs, Jock's friend. I believe you have something lined up for us."
"See that big black car? That is waiting for us. This lady likes a gang bang and she has several friends who do so also, but there will only be two at any one time, so you should be able to bang two women today. Feel up to it?"
"Hell how did you latch on to this set-up. Of course I'm with you 100%." He said smiling.
We waited on Jock and Peter, and then we walked with a fast step towards the waiting car. This time the journey didn't seem to take as long as the first time and once more I was standing at Eleanor's front door. Eleanor was dressed in a housecoat, wearing slip on slippers, her hair was brushed out and hung down her back as far as her waist.
"Well I see you brought your friends as I asked. Nice to meet you lads, come into the lounge were we will get to know one another."
As we followed her in, the lads were smiling and giving the thumbs up sign and it was obvious they thought this was the greatest.
"You can put your things against the wall there. I think you should just strip down to your underpants. See I will do the same," Eleanor said dropping her housecoat and standing before us in a similar knickers and bra as last week but of a different colour, this week it was red, last week white.
Jock's eyes nearly popped out of his head, as he looked Eleanor up and down. She too was giving my friends the once over and she settled on Sam. "I see I have made an impression on all of you," gazing at the large lumps appearing on our groins. Come let's make our selves comfortable, while we wait on my friend Jessica."
Like last week we sat on the sheepskin rug and I could see the lust on all the lads' eyes. I was just as bad, for Eleanor had a lovely full body and I'm sure they were eager to sink their cocks into her.
The door opened and in stepped a woman all of us knew, it was the Captain's young wife and she just shed her housecoat when she locked the door. All she had been wearing was a smile under her housecoat.
"Do I get to choose or are whores not allowed to do that," she said in her upper-class voice.
"I think the first time we'll let you have that privilege Jessica," Eleanor replied.
"Then I'll have the big lad. Now come on son don't be shy take your underpants off and let Jessica see what you have."
I did as she asked and so did all the others. I saw that all of them were well-endowed, so these women won't be disappointed with little cocks today.
"Oh my, you are a big lad and Jessica is going to enjoy this. Please lie down I like to be on top." She said.
Getting astride me she just lowered herself down and she was another like Eleanor. I am sure she had to put a lubricating Jelly in, for she slipped down so easy. There sitting on my cock was the Captain's wife, the woman who was always present at Divisions on a Sunday and every boy would have liked to get between her legs. She was in her twenties, auburn shoulder-length hair, I would guess a thirty-six inch bust and thirty-eight inch hips with a twenty-four inch waist. She looked like a film star, with her long shapely legs. Why was she here, she could have chosen any number of men who would have loved to go with her, yet here she was sitting on my hips with my cock buried in her pussy.
"You like Jessica? I suppose you are Frank whom Eleanor was telling me about."
"Very much so, you are a beautiful woman and I love the way you are working my cock," I said that for she was rolling her hips in circles and sending fantastic feelings all over my body. Also she had soft buttocks which moulded on my thighs.
She leant forward and started moving her hips back and forth and smiling at my reactions. I reached up and drew her closer and pressed my lips on to hers. It was then she cried out and then I looked up and saw Jock behind her holding his cock in his hand and advancing on her rear. As he shoved his cock into her rectum I felt him between the thin membrane separating the two holes and then the movement of his cock fucking her. Jessica started moving back and forth in time with him, she was being fucked in two holes at the same time and she appeared to like it.
Jock shot his bolt and then withdrew and Jessica let out a sigh. "Oh you boys sure know how to treat your whores."
She then continued fucking me, kissing my lips and all over my face until we both climaxed almost simultaneously. She just lay on top of me pressing her lovely breasts on to mine. I had my arms around her as though comforting her.
All I heard from the other side of the square was the sound of flesh striking flesh and a slurping sound, but I was happy lying with this woman encasing my cock. It must have been fifteen minutes before we detached and sat up.
"Eleanor, you have picked the right ones here."
"I know, the two I had just suited me fine, but it is Frank you have to thank for bringing them together."
"Oh I will, don't you worry about that Eleanor."
Just hearing two naked women talking the way they did made me hard again. I pulled Jessica towards me again and got her on her hands and knees and slid my cock into the lovely slippery pussy I had only recently abandoned.
"Oh this is really something, twice and under half an hour," Jessica said wriggling her bottom hard on to me once more. Sam seeing Jessica in this position knelt in front of her and placed his cock in her mouth, which she started sucking. Sam was there to fuck her face and he started pumping his cock into her mouth, faster and faster, making her choke a couple of times. I kept up my steady pumping and after Sam withdrew spluttering his sperm all over her face and neck. A good few minutes later I spent inside her also.
This time instead of letting my stay in her pussy she rose. "I must go and wash this off my face." She sounded angry as she said it.
"I could do with a wash also I'll come with you."
"Thank you I appreciate that," she answered smiling, even though Sam's spunk was running down her face.
I grabbed Eleanor's housecoat and followed Jessica to the bathroom. She turned on the shower and we both got in under the running water. "Disgusting boy, I hate having sperm spurted on my face. I'm also not too partial to sucking just any man's cock either. Now you Frank are a different kettle of fish, I was willing to take part in these Sunday romps, but I would rather spend my energy satisfying you. What do you say we have a little tryst just between ourselves?"
"You know I can only get leave on a Sunday afternoon."
"My husband plays golf every Wednesday and Saturday afternoons and then dines in the mess and seldom home before ten. You know you can access my home straight from behind the administration block. I'll make sure you get permission to be in that vicinity, then I won't have to come here and have that disgusting stuff sprayed on my face. You know if you like variety I can get a few friends to visit during these times." She said with her arms around my neck staring up at me.
"You have it all worked out, you devious woman."
"I somehow knew you were just right for me. I've always wanted to see what a large cock would feel like and I love it and want more and more, say you will do as I ask, please."
"How could I refuse such a beautiful woman?"
"You mean sexy woman," she said now dropping her hand and gently moving it along my semi hard penis.
"Keep doing that and I will have to put it back into that lovely warm pussy of yours again."
"That is all I get these days is promises," she said laughing.
I've never been hard so many times in such a short time. I may not have been the hardest I've ever been, but hard enough to enter her expanded pussy. I lifted her up and she wrapped her legs around my waist and I guided my cock back into her now washed out pussy. This time she lowered herself slowly down with her wedged in the corner, she was trapped.
"Oh Frank, I want you to stay where you are. I have never felt so comfortable with a man before as I am with you. You are bringing all my lustful thoughts to the fore. You must come and see me on Wednesday afternoon, come about two. I will clear it, don't worry, just let me feel you inside me that is all I ask." She said hugging me and kissing me at the same time.
This woman was far more active and demanding than Susan ever was, but being a young man I couldn't get enough of her. Jessica was what all young lads dream of, getting your end away at the drop of a hat. We ended on the floor as I plunged deeper and deeper into her slippery pussy, but I just couldn't shoot my fat. We stopped and then continued to wash each other. I loved the way her breasts moulded in my hands and the softness of her buttocks when I slid my hands down her back.
"You know more of my body than my husband does. He has never been in a shower with me as you are now; he is a straight-laced man. The sex act, I think he feels it is dirty and the quicker he gets it over the better, no wonder I felt frustrated. But you have calmed me Frank, so I have to thank you for that. Now I am not returning downstairs say my goodbyes will you, and I'll be seeing you on Wednesday," with that she kissed me and left the shower.
I dried myself and went back down, and in the middle of the rug was the three of them all fucking Eleanor. By this time she must have been topped up in every hole in her body with spunk. Peter was underneath with his cock buried in her pussy and Jock was rove up her arse, while Sam was fucking her in the head. I think Jock loved fucking arse better than pussy. Peter was like me, he preferred pussy and he was the biggest of the three of them. If Jessica manages to get a few of her friends I think I would only take Peter with me now I have seen the rest of them and the way they treat a woman. The only thing it looks as if Eleanor is lapping it up.
There was no need for an extension and by now everyone was knackered. The four of them went up to the bathroom and Eleanor was the one who came down first.
"Well was that what you wanted, you seemed to enjoy yourself," I said to her when she came into the room.
"That was just what I wanted, but I think I'm going to be a bit sore in the morning. I see you and Jessica got on champion, it's a wonder for she is a fussy woman. If you want to get on in the Navy she is the one who can help you as well as being a good fuck. You do as she asks and you will have no more problems. Will I be seeing you next week?"
"Do you want me to come?"
"Oh yes and bring your friends too,"
When the lads got back down I had dressed and Eleanor had put her underwear back on as well. They just looked at us and started dressing. After a coffee we were driven back to the Establishment, but there were three happy mates of mine now. All agreed to come again next week.
On Tuesday I was called into the Divisional Office and told that I was to be the Captain's messenger. This was a position which was done by a PO Boy and who accompanied the Captain on his Saturday rounds and Sunday Divisions. Most importantly it allowed me to access the laneway to his house, just as Jessica had said she would arrange. Now there was only one PO Boy more senior to me, but that was Peter anyway and he was beholding to me anyway.
Using my new position I approached the Captain's house rather apprehensively that Wednesday afternoon. Standing at the front door was Jessica dressed in a housecoat and I knew what that meant, she was naked underneath. She held out both hands palms facing downwards.
"I was worried you would get cold feet, knowing what you boys think of coming to this house. It's all the safer for us, as I know no-one will disturb us. All the stewards and cooks are off until this evening, so let us go to my bedroom."
The door was hardly closed when she had her arms around my neck showering kisses on me and pressing her body against my hardening cock, for she had put on extra perfume and she reeked of it. Jessica helped me undress and almost tore my clothing off and pulled me down on top of her on her bed. Once more I was between the legs of the most perfect woman I knew and I felt her guide my cock up into her already profusely secreting pussy.
The feeling I got was that I was home where I belonged, for Jessica was a very soft woman, but somehow managed to work her vagina in such a way the sensation went right through my body. This time we fucked slow and easy as I held her buttocks to gain more depth.
"Use a pillow under my hips Frank and squeeze my breasts, I love the way you done it on Sunday."
For the life of me I couldn't remember how I felt her breasts but I think it may have been Jock when he was rove up her arse and leant beneath her and held them. I did as she asked though and massaged her two more than a handful orbs with the hard nipples as I sank my cock into her depths. Slow and easy was the way I liked it and I wasn't partial to sinking my cock in her shit hole. I liked the one Mother Nature provided and that suited me just fine.
Fifteen minutes I lasted and must have been one of the longest fucks I ever had before shooting my load into her. This time like the first we lay entwined after our climax. Her eyes shone and she kissed me with little kisses and smiled.
"I feel I'm floating on a cloud, I also like the way you treat Jessica after your finished, by just leaving it in."
"I honestly like to feel a woman wrapped around my cock, it is the best feeling in this world."
"Any aged woman is that what you mean?" She asked.
"Yes, any woman, but especially you. Somehow you feel just right for me Jessica and I feel comfortable with you."
"Just comfortable?"
"I have been thinking about this for the last few days, and looking forward to doing what we are just now, lying close to each other."
"I know what you mean; I feel the same way too. Would you do anything for me?"
"What do you want me to do?" I asked wondering what it was.
"Give an old lady what you have given me today and on Sunday?"
"If you want me to do that then I will, who is the old lady?"
"Never mind who she is, I told her all about you and she too wants to feel a big cock slide in her pussy. You know I never experienced a big cock until you slipped that monster of yours into me. I though you would tear me apart, it gave me the greatest pleasure I ever had. So there I have exposed myself to you."
"So when do you want me to see this lady?"
"Here on Saturday, but after I have felt this monster inside me, it's now like a drug to me, I just can't get enough."
Once more we coupled and then I had to leave because we could hear the kitchen staff below and one thing we didn't want was to be caught out.
Saturday afternoon I was greeted the same as I had been on Wednesday and it was almost a copy of Wednesday. Today though afterwards, I lay on my back with Jessica in the crook of my arm. Just gazing up at the ceiling, was I doing wrong I thought, or am I suffering from some mental disorder, like teleiophilia or even gerontophilia since I was attracted to women older than myself. I was brought out of my thoughts by Jessica's voice.
"Frank, what I am to tell you I have never told any man before, you must believe me. I love you Frank, I don't know what I'm to do when you leave here." She said then started crying.
It was strange her saying that, even though we hadn't met that long I really liked Jessica, more than any of the others I'd fucked.
"I honestly like you very much Jessica and I really will miss you. I wish there was some way we could be together. I would even settle for short periods."
"I had a funny feeling you had a soft spot in your heart for me. I am finished with my old ways and you are the only man for me."
"Plus your husband."
"Frank, our marriage is one of convenience; he has his room I have mine. Yes I let him relieve his animal lust from time to time when he can't find a willing partner. There are many officers' wives who curry his favours on behalf of their husbands that his visits to my room are very few and far between. Now, even he will be barred. Please go and see the lady in the room next to this she will be wetting herself in anticipation. I will see you next Wednesday here. Of course I'll be seeing you on the parade ground at Divisions, but that isn't holding you close. Now go before I make a fool of myself."
I collected my clothes and tucked them under my arm. Why should I get dressed the woman next door knew what I was coming for and I would have to get undressed again. The house was centrally heated and the cold February weather was kept out. When I opened the door an elderly woman rose to her feet, she too was dressed in a housecoat. She looked nervous as I closed and locked the door behind me.
This woman was in her late sixties or early seventies, and just the sight of this small old woman made me feel sorry for her. Why was a woman this age wanting shafting, but then again a pussy was a pussy and as long as I had it up a woman I was happy. I placed my clothes on a chair and walked over to her. Taking her face in my hand I kissed her fully on the mouth. I knew she never expected this as she drew back a bit, but then she put her arms around me drawing me towards her.
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