Females with Sissies

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MsGary

TG/TS for all men
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Sep 3, 2005
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It is all the rage right now for women to have a sissy best friend. We sissies know fashion and colors (esp shades of Pink) and all the latest femme news.
There is something that women know which is Not mentioned too often. Bois like me know how to touch and kiss and please another person. Some women and older girls like to take advantage of this fact.
Because a Sissy Boi has served cocks in various ways, We know how to please a woman too. I was married to fame for 11 years until she divorced me when she turned 40. When we got engaged she actually arranged a sex date for me with a girl my own age. The girl was a virgin to cock , just as I was a virgin to pussy. I had never fucked a Man yet either by the way.
Her name was helen and she went to a high school that was winning all of their swim meets right up to the state championship. Anyway, that was how I knew her. She was not pretty but she was pretty cute. Bu thte body. so slim but busty. I now estimate 36DD-23-34. A rich girl but It never crossed my mind that she might have a boob job. I had not seen or felt many breasts yet. Anyway, because i had served men before I knew what I Liked and I imitated what I liked , doing it to her, with her. She liked /Loved nearly everything I did. Her nipples were not as sensitive as mine. but she loved how I treated them. she said I was very skilled. She played with my cock too but did not suck it. She also did not comment on how short it is. She did ask why I had boobs. I just told her honestly but not complete truth, that I was more like a girl than a boy.
Helen said she had heard that. But SHE did not think i was THAT girly. I never knew if she was just being kind, since I was trying to get ready to fuck her.
I will tell about the intercourse with Helen later.
Love, Heather
 
Heather I know what you mean I quit few girl friend. An they always want me to go shopping with them because of my taste in clothes.I have also made love to tow of them a couple of times.
 
That is Fantastic. Suets. What a great pic of you. May I ask how old? I will be 21 in 3 months. I have never had sex with a female and it may not happen. But I sure feel like I have had chances. Maybe more times than i realized---I sure am not tuned in to that with females. More like I know what they need as a girl and me as their "girlfriend". I have feminized with hormones alone. as far as anything textra. Di dyou do hormones and exercise also. no surgery? You have perfect perky tits and GREAT legs. You are mor hung than you said before I think.
Love, Mary (my real and legal name for 3 years. CALLED Mary for over 5 years
 
suets said:
Heather I know what you mean I quit few girl friend. An they always want me to go shopping with them because of my taste in clothes.I have also made love to tow of them a couple of times.
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Suets, Thanks so much for response ! I do not think i have seen that revealing a pic of you before. REAL nice. Where is that beach. ? Swimming is my main sport-compete and recreation- I will follow up with this thread later. Esp since I have made some promises. I am 52 now and i believed I joined the site when 41.
Thanks again and love hearing from YOU!
Love, Heather. My first four lovers were just a few years older but then 3 or 4 guys in their 40's ; They were GOOD! yes, 1 whtie and 2 or 3 black.
 
I promised I would tell about my sex date with Helen K. Will follow with that.
 
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I went to a home cooked dinner with Helen's family. They knew of me but wanted to meet me. They lived about 29 miles away. Now it would be 40 but does not matter.
WE had a second date, just the two of us. There was kissing and hugging and massaging each other. i STILL feel bad that I never noticed her. Even if just for her body AND the fact that she liked my slim strong body. She let me touch her however I wanted, but I did not push the priviledge. She appreciated that but did not say anything. she DiD tell me that the only Man who went that far with her was a military man who visited every couple months and HE was much older, like 45. I felt the need to tell her I had been affectionate with men in their 40's.
She also liked my slim strong body! She knew all about me (not just from me telling her).
Then something I had not seen before. She asked to find a rest room and she handed me a toothbrush in the seal and a travel tube of toothpaste. She showed me her fancy electric toothbrush and pointed to the men's room she said "we DID have onions". Of course I thought 'This girl Really cares about hygiene !' Sure made a good impression on me.
The actual sex was on our next (3rd) date.
 
For our third date , I actually went to her house again. I felt like such a nerd (which I am) getting dropped off by my grandparents. Hellen's parents and her little brother were there too but getting ready to go out to this saturday nite dinner. We all sat in the living room talking. Mainly they talked about Helen , kind of bragging on her. She had scored some ungodly number on her SAT's. She would be one of the few 17 yr olds starting at West point. I did not even know. She was finishing her senior year. The talk among me and my 11th grade classmates was not about college.
I though about helen's fitness and how smart she was. An academy made sense. I was getting hot for her.
I do nt know how often a boy is chosen by her parents to be her first lover. And SHE was "chosen" by my grandparents for ME. They all left at the same time and Helen's mom called back "have fun you two.!" I admit I watched to see two cars head out the drive and down the main road. She tapped the place on the love seat next to her for me to join her. She took off my glasses and put them on a table. She had already taken off hers. WE kissed and I wondered why I had not done this more with girls.
I was glad I knew how she liked to be touched. We had been massaging each other for over a year but we did not count that as dates. She also put my hand on her breasts. "You are so slim!" she said thank you. She knew she was awful skinny to have boobs that big. I noticed how sheer and sexy the material of her dress was. She also was braless. She hardly ever did that except maybe after a shower under a robe. And I had seen her in her brown bikini.
WE headed for Her bedroom as she told me the "rules" for this night, the main thing was that I was to wear a condom. Helen had gone on the pill nearly a year before ( i believed her when she said she did THAT for me). She was nude as soon as she entered her room. WAS wearing ONLY her dress and 3 inch heels. Ihad just started undressing. She said "no hurry" But "what are you waiting for" -teasing me.
She laid on her side on the bed watching me. When fully nude I joined her on the bed. I was hard just form being with her. I laid on my side next to her and we kiss again. She did not touch me below my waist , Yet!
 
I actually dreamt about Helen K. last night. In her own bed I touched he thigh. She moaned a little. She put my hand on her big breast. I sucked the other one. As I flicked my tongue across her nippl, she moved Louder. As I said, Helen knew ALL about me. sh employed with MY little A cup tit and kissed them and sucked each nipple briefly. I moved my hand up her thigh and del that shot wetness. I reached for the lube and Helen stopped me. "I do not need that"; not with You"! She slid her leg under me and pulled me on top of her. My short thin penis lined right up with her love hole. She was tight in there but at the same time did not take much force to enter her. Along with the condom requirement she also told me about the one finger rule.
I felt so comfy with her. More so than with my fiancé`. She told me anything I asked her and also as things came up she explained. I was on her pumping in and out for 5 or 6 minutes and she rolled me over. She held me down and ground on my little sick cowgirl. This was just as thrilling. She even told me she was a cowBoy, not a cowgirl! "I have always thought I was supposed to be a BOY. !" I said 'me too' "oh you have always thought you were supposed to be a boy. ?" he he. She knew I felt like I was (should have been a girl).
I relaxed and let her do ALL the work now. Less than ten minutes later she drew the cum out of me. I could feel it filling the condom. A couple moments later she rolled off and took off the rubber. She squeezed some of the remaining jjism out of my penis and tasted it. she said mmm. Helen said she had no idea if she would like to eat cum but that mine was ok. Kind of erotic to finally do it. One thing was the t she did to want to go off to West Point a virgin.
We lay next to each other relaxing and talking about other things besides sex and college and the Army. I di snot even know if i might get into college next year but I thought about doing the Army thing where you could do boot camp between your junior and senior year.
Love, Heather.
 
suets said:
Heather I know what you mean I quit few girl friend. An they always want me to go shopping with them because of my taste in clothes.I have also made love to tow of them a couple of times.
Click to expand...

Suets, May I ask how long since you could get erect? It is bigger than you implied before! I am just worried about mine. I have never fucked anybody , yet. A couple more years and I will probably not be able too. They say it is all in my head. Maybe true because I have been fully trained and bitched.
luv, Mary
 
I just cannot wait to get to Cuba dn see all of the things Americans had been missing. Of course I wan to get to the islands where the whit eBOIS are having Black MEN's babies
there must be a lot of medical help involved. So exciting though. Of course So Many bois competing for attention of a few dozen black men must complicate things. I was following that story closely when it was pretty active. and I cannot wait to hear more from Trinidady or Ms Gary.
Love, Mary. HOPING for Cuba visit THIS fall or winter.
 
18mDresdF4prom said:
Suets, May I ask how long since you could get erect? It is bigger than you implied before! I am just worried about mine. I have never fucked anybody , yet. A couple more years and I will probably not be able too. They say it is all in my head. Maybe true because I have been fully trained and bitched.
luv, Mary
Click to expand...
If you are asking all the older sissies on here (Sue not really 'older' just more years than Mary). Anyway, 18 years now since I was getting hard regularly.
Takes a lot of sistimulation Now. Best way for me to get aroused in that way is to be with TWO men. you know, 2 mouths 4 hands 2 cocks
Less and less hard ons since age 34. WAs divorced at 28 so….
Love Heather
 
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