I've often wished that I was a woman. I would assume I'd have that ability to expertly put on make-up, so I would get myself all dolled up, put on some sexy yet not slutty clothing, wear my favorite pair of shoes, and go out on the town. I'd shop for more shoes and clothes. Next I would hopefully find a male with several friends. I'd let them hit on me and play a little hard to get to them. Eventually, I'd give in to their advances and let them take me where ever they wanted to go. I would let them strip me and get me ready for one hell of an afternoon/evening/night and try as many different sexual positions as I possibly could. Most of all, I want to have multiple orgasms during the course of the evening/night, as well as being pumped full of their juices.
Once the sex was all over, and it was near time to turn back, I would pray that I could keep everything as it is. During the last couple of minutes as being a woman, I would cry my heart out knowing that I would be turned back to a man.
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JessieCD
Over 90 days ago
Fluid Gender questioning, 53
0 miles · Minnesota
Forum
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While driving her home, she started getting frisky and took my cock out and started playing with it. I decided to escalate the adventure by playing with her pussy until she orgasmed. She then promptly started giving me a blowjob while going 70 down the highway. A hell of an experience, and thank god not a lot of traffic.
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Nothing feels better than to ride that 7" dildo of mine (or course a real man would do as well). I just love sliding up and down on it, and then once fully inside of me, I rock back and forth. Grinding on that marvelous piece of near real cock. I will ride it for nearly an hour before I give in to my own orgasm. If the real deal were present, I'd let him take me and make me feel like a real woman.
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The lady I used to date, we would have all night sessions (7 - 8 hours) of which I would average cumming 4 or 5 times. I think the longest time between orgasms for me was 3 hours or so. But what I thought was better was seeing her go through many more orgasms between mine. It was a shame it didn't work out as we were very compatible in bed, and it was always a fun time.
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There are so many things I envy that a woman is so fortunate to have in their lives.
Top on my list would be the ability to get pregnant, carry, and give birth. I know it isn't always the most glamorous of times, but those times pale in comparison to having the ability to have a precious life grow inside of you. The complete unconditional love that you feel for the baby growing inside of you even though you haven't seen or met the new little bundle of life is something no man could fully understand (been there from a man's point of view). That would be my number one.
Other things I envy are:
That women for the most part can dress-up however they want (Causal, sexy, in men's clothing, etc) without an overwhelming part of the population thinking something is wrong with you or laughing at you.
A woman's form (shape)
The amazing shoes!
The soft fabric choices and variety of clothing. Yes, men have some choices, but for the most part they still are not as soft and comfortable as the fabrics women tend to have.
The emotional connections they make in a relationship. Yes, men make those too, but after comparing mine and my male friends to my female friends, it seems different.
Can be sexy in the sexiest of clothing, or in a sweatshirt.
Experiencing out of this world climaxes. At times, my last female lover would hit a state that she would be shaking all over and be there for almost a minute if not more. She would try to explain what she was feeling, but she could not find words. These were way different than other climaxes she had. I can remember the first time she got there with me, it blew me away how different it was. Don't get me wrong, a man's climax is pretty intense, especially the longer you are on the edge. However, I have never experienced anything close to hers.
Sure, there's more. These are the ones that hit the top of my list.
Top on my list would be the ability to get pregnant, carry, and give birth. I know it isn't always the most glamorous of times, but those times pale in comparison to having the ability to have a precious life grow inside of you. The complete unconditional love that you feel for the baby growing inside of you even though you haven't seen or met the new little bundle of life is something no man could fully understand (been there from a man's point of view). That would be my number one.
Other things I envy are:
That women for the most part can dress-up however they want (Causal, sexy, in men's clothing, etc) without an overwhelming part of the population thinking something is wrong with you or laughing at you.
A woman's form (shape)
The amazing shoes!
The soft fabric choices and variety of clothing. Yes, men have some choices, but for the most part they still are not as soft and comfortable as the fabrics women tend to have.
The emotional connections they make in a relationship. Yes, men make those too, but after comparing mine and my male friends to my female friends, it seems different.
Can be sexy in the sexiest of clothing, or in a sweatshirt.
Experiencing out of this world climaxes. At times, my last female lover would hit a state that she would be shaking all over and be there for almost a minute if not more. She would try to explain what she was feeling, but she could not find words. These were way different than other climaxes she had. I can remember the first time she got there with me, it blew me away how different it was. Don't get me wrong, a man's climax is pretty intense, especially the longer you are on the edge. However, I have never experienced anything close to hers.
Sure, there's more. These are the ones that hit the top of my list.
Yummmm! Active Ink Slinger
Very. Very. VERY carefully. Lots of shaving cream or shaving butter, a nice sharp blade, take your time, and pull you cock out and/or get it hard so the skin is as smooth as possible. Nothing worse than having the blade nick you because it got caught in loose skin, it can bleed a lot.
For those nice danglies, same advice as above, but squeeze just above the balls and make themstick out so the skin is stretched.
An absolute must is don't rush it!
For those nice danglies, same advice as above, but squeeze just above the balls and make themstick out so the skin is stretched.
An absolute must is don't rush it!
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As Jessie, no doubt about it. I recently purchased a dildo and have been practicing on it. The more I practice, the more I would love to feel a real man get hard in my mouth. I'd love to feel the velvety soft head enter my mouth and the contour of his shaft as it slid past my lips. I'd play with it, lick, suck, try to deep throat it, and keep him on edge as long as I could. To feel the sudden hardening and release of his hot creamy load onto my tongue would give me the feeling of power and satisfaction that I made my man cum. It would make me a very happy gurl.
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Unfortunately, she broke the trust between her and her boyfriend by being with you and him finding out. It is best for your safety to let it go and not approach her boyfriend on the matter. As she is responsible for her own actions, she is the only one that should attempt to salvage her relationship with her now ex-boyfriend.
Based on what you wrote, it seems to me that you have more than a "severe case of mutual infatuation" with this woman as you seem to genuinely care about her well being more than just the infatuation you experienced. If that is true, you are also in a hard position and will need to do some serious reflection on how to handle it. Either way you go, someone will likely get hurt. It is up to you, but my opinion is that you should come clean with your girlfriend of ten years (my two cents, other's may not share that opinion). Especially since she invested ten years in a relationship with you.
Whay ever route you go, I wish you well.
Based on what you wrote, it seems to me that you have more than a "severe case of mutual infatuation" with this woman as you seem to genuinely care about her well being more than just the infatuation you experienced. If that is true, you are also in a hard position and will need to do some serious reflection on how to handle it. Either way you go, someone will likely get hurt. It is up to you, but my opinion is that you should come clean with your girlfriend of ten years (my two cents, other's may not share that opinion). Especially since she invested ten years in a relationship with you.
Whay ever route you go, I wish you well.
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As a bi-curious closet crossdresser, I have seriously struggled how and when to let friends and family know that I really enjoy wearing women's clothing, have thoughts of being with a guy, and my desire when I dress up to be a woman. My family are very accepting of homosexuals as my uncle is open with the family. However for some reason they think that a male that likes to wear women's clothes is weird and a male that wants to be a woman has issues. Needless to say, I'd love to let them know so they don't get a shock if they found out accidentally, yet I am terrified of the responses I would get from my friends and family.
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It is amazing how once I took the plunge and ordered some heels and a Halloween costume, that I am totally hooked on women's apparel. Lately, I have found myself browsing women's clothing and shoe sites to find that next sexy dress or shoes for me to purchase. I just recently bought a hot little leopard print dress and some silicone breasts to help accentuate my figure. I can't wait until I have a moment to wear them. When I am my alter ego Jessie, I get really hot and bothered. I will spend hours pretending I am that lucky girl riding a handsome strong man. Even though I have had comments about my girlish figure, I am not lucky enough to have more feminine facial features to become fully passable. 
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One time I started laughing because for some reason we were not in synch with each other's moves like we usually were. My wife at the time dead panned stared at me and asked "What's so funny?" I laughed a little more as I was explaining how we just couldn't synch up. She rolled over and said that there is nothing funny about sex, and went to bed.
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For me, the 10 - 20 seconds prior to orgasm, I feel a building pressure as my nerves continue getting stimulated from pleasing my woman. The last 5 seconds or so, I feel my cock swelling and becoming harder and harder. I let the pressure build and then I hold it as long as I can. Upon release, I feel a wave of absolute pleasure that washes over my entire body. For each release, a slightly smaller wave of pleasure washes over me until a final release occurs. What really amplifies my feelings during orgasm is when I see the pleasure and release on my lover's face and body. Knowing I pleasured her to her own orgasm really makes the entire experience.
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