Having Sex With A Shemale
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Having Sex With A Shemale
What to expect when having sex with a transsexual girl for the first time
Again, I think this depends on the person. For example, when bottoming, I personally dig positions like cowgirl where I can look in my lover’s eyes as we make love. When topping, I love doggie style because it gets me in the right mindset to fuck the living shit out of someone.
By SimplySxy Editorial Team February 25, 2020
By Dr Michael Justice January 6, 2020
By Taylor Lianne Chandler October 24, 2017
Sex is one of the most connective experiences we can have as human beings. By my nature I’m a very sexual human being – so it permeates a lot of how I interact with the world around me. To me sex isn’t just limited by acts of penetration… there’s a whole world of ways to get your rocks off, and I like to explore every way possible particularly when we get into the kink scene. I’ve a personal motto, “Try everything twice. I may have just been in a bad mood the first time.” It’s led me to a lot of sexual experiences that I really enjoyed that I might not have ever tried if I was more timid.
Primarily I enjoy sexual encounters best with people I care about, but I also don’t particularly respond well to labels being assigned to those relationships. I’m an ethical slut… while I have sexual relations with multiple partners whom I am close to, it’s important for me to be open and honest with everyone as to what’s going on. If I was born earlier, I’d definitely have fit in amongst the free-loving 60s. The sexual roles I play with my partners (top/ bottom) changes from person to person based on what our connection with each other is like.
I also dig my sex being safe, sane and consensual. As great as sex is, there are some risks involved given diseases. That means both giving and receiving respect from partners, including being up to date with STD testing. It means making sure we learn and respect each others sexual boundaries. Sex is an act of trust and trust needs to develop from open and honest communications – about likes, desires and even fears. You can have sex without that level of trust, but in my experience that type of sex isn’t nearly as fulfilling.
Just chill. Don’t rush into anything. Start with the simple stuff… Touching one another. Caressing. Kissing. Foreplay is all about relaxing — about pulling yourself into the moment, Did you know that some of the most erogenous zones on the body have nothing to do with genitals? When I’m with a new lover the first time, I like to explore as much of their body as I can before we move into fucking. It helps me learn who they are and how best I can give them pleasure.
If you focus on these small interactions with your partner, the sexual tension builds until it’s natural to orgasm. It’s very similar to an idea which actors profess, “be in the moment.” The best sex involves losing yourself in the immediate acts of lovemaking rather than focusing on anything else. Let’s face it — when it’s good, time stops. There’s no thought other than the pleasure you and your partner are having. I find organically getting there through foreplay is the best way to relax during my first time with someone.
That all depends on the transsexual woman. Is she a top or a bottom with you? How comfortable is she with her own body? One thing that’s key to understanding transsexuals is that because we were born in a body that’s inconsistent with who we are, we experience some level of dysphoria from it. This varies from person to person. Personally I’m okay with the fact I still have male genitals. While I would have preferred to have been born with a vagina, I’m okay with both lovers and myself pleasuring my cock – it doesn’t trigger emotional discomfort for me to use my cock during sex. But there are other transwomen who can’t bear to see their cock let alone to have it touched or used during sex.
If you want to have a great sexual experience with a transwoman, you’ll need to have communication with her. How comfortable is she with her body? Does she want to penetrate or be penetrated? Like any other sexual encounter, you and your partner will need to negotiate what’s enjoyable for both of you. Once you are past that, it’s just like any other sexual encounter.
There’s a whole world of kink out there. Google it – lol. Some of my personal favorites include electroplay and ropeplay. Fifty Shades of Grey barely touches the surface of what’s possible. For folks wanting to explore BDSM, I suggest starting with a book called “The Loving Dominant” – it’s not a perfect book by any means, but it does cover both the physical and emotional aspects of dominant/ submissive play and is a great introduction to those concepts.
TS porn star Wendy Summers was the 2013 RISE Shemale Performer of the Year and a three-time Transgender Erotica Award winner. Wendy has appeared in the DVD releases I Kill it TS Vol 1, Shemale Strokers 50; Bang My Tranny Ass 10; and 5th Annual Tranny Award Winners and has appeared on websites like Shemale Strokers, Shemale Yum, Shemale Pornstar & Wendy Williams XXX. Read the rest of her profile below and the links to her website www.WendySummers.com !
Images courtesy of Wendy Summers
Have an amazing experience or tips you like to share on SimplySxy? Drop us an email at editorial@SimplySxy.com !
Funny, geeky and a little bit freaky, TS porn star Wendy Summers has been captivating fans worldwide with her unique personality and style. She was the 2013 RISE Shemale Performer of the Year and a three-time Transgender Erotica Award winner. Wendy has appeared in the DVD releases I Kill it TS Vol 1, Shemale Strokers 50; Bang My Tranny Ass 10; and 5th Annual Tranny Award Winners and has appeared on websites like Shemale Strokers, Shemale Yum, Shemale Pornstar & Wendy Williams XXX.
Her solo website, www.WendySummers.com launched in February on the Grooby Network. Of her website, Rabbit Reviews remarks: "She's a genuinely creative and playful person adding to the sexiness... her personality makes this site worth checking out." Review Shemales raves: "[Wendy Summers] is a unique and refreshing transsexual and I think many will relate to her off beat personality!" Her Wendysummers.com features solo and hardcore pornography as well as fetish photography which allows her offbeat personality shine. Whether a geeky cosplay, an intimate girlfriend experience style scene, or a kinky bondage scene, Wendy brings a uncommon and delightful spin to the world of Transsexual porn.
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Have you ever had sex with shemales?
Former Retired at Architectural Designer · Author has 1.8K answers and 3.6M answer views · May 26 ·
Has anyone been tricked into having sex with a shemale? How was the experience?
I'm a guy. If I have sex with a transgender man, am I gay?
What is it like to have a shemale cum in your ass?
What does it feel like to have sex with a transgender woman? How is it different than having sexual intercourse with other women?
If a heterosexual man wants to have sex with a trans woman, is there something wrong with him?
Has anyone been tricked into having sex with a shemale? How was the experience?
I'm a guy. If I have sex with a transgender man, am I gay?
What is it like to have a shemale cum in your ass?
What does it feel like to have sex with a transgender woman? How is it different than having sexual intercourse with other women?
If a heterosexual man wants to have sex with a trans woman, is there something wrong with him?
My husband has admitted having sex with a trans woman who still had her penis before we met. I’m so shocked, but OK with it, but I'm confused as to what it means about his true sexuality. What should I do?
How many straight men have had sex with trans people?
Do women suck penis better or shemales/ladyboys?
I want to be a shemale and want my wife to have sex with me as a lesbian couple. How do I persuade her?
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Has anyone been tricked into having sex with a shemale? How was the experience?
I'm a guy. If I have sex with a transgender man, am I gay?
What is it like to have a shemale cum in your ass?
What does it feel like to have sex with a transgender woman? How is it different than having sexual intercourse with other women?
If a heterosexual man wants to have sex with a trans woman, is there something wrong with him?
My husband has admitted having sex with a trans woman who still had her penis before we met. I’m so shocked, but OK with it, but I'm confused as to what it means about his true sexuality. What should I do?
How many straight men have had sex with trans people?
Do women suck penis better or shemales/ladyboys?
I want to be a shemale and want my wife to have sex with me as a lesbian couple. How do I persuade her?
How can I find a shemale for a threesome?
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Well not intercorse but my wife surprised me on my birthday with one of her girlfriends that is a transgender black and OMG seriously she has the absolutely biggest penis I've ever seen in my life honest to God, she was still soft and it was hanging there and it was at least 10 inches seriously she said she was so excited when Kelly my wife asked her to come over for a surprise birthday present for her hubby, but I was completely amazed by her size, I couldn't help but keep thinking how big is she fully erect, so my wife goes into the kitchen to get drinks and I said to this absolutely perfect
Well not intercorse but my wife surprised me on my birthday with one of her girlfriends that is a transgender black and OMG seriously she has the absolutely biggest penis I've ever seen in my life honest to God, she was still soft and it was hanging there and it was at least 10 inches seriously she said she was so excited when Kelly my wife asked her to come over for a surprise birthday present for her hubby, but I was completely amazed by her size, I couldn't help but keep thinking how big is she fully erect, so my wife goes into the kitchen to get drinks and I said to this absolutely perfect in every way girlfriend I'm not even touching myself and I'm fully erect just sitting there next to her, so she looks me directly into my eyes and says I have never been experienced such a wonderful gentleman as yourself Tommy I am very flattered by your respect and I have noticed that you haven't taken your eyes off my dick may I ask you why? Omg sweetheart are you serious look at that incredibly beautiful and extremely big penis of yours, what about it sweetie, and she takes my hand and starts rubbing her penis with it, you know what baby it's very hard to get it fully erect being as big as it is I haven't had anyone able to get it fully erect without me playing with it, Holy fuck sweetheart no way seriously, I consider myself the ultimate pro at pleasuring a penis, she said yes that's what Kelly told me to well I have a deal to offer you if you are interested?Omg yes I'm interested, and Kelly comes walking in and says well did he take your offer, I said yes I did, so you are in on this with her aren't you? No sweetheart I don't know what the deal is just that she was going to ask you something, OK here's the deal, I've known Kelly for a couple of years now and I've never told her that I've been wanted to have her as my lover and best girlfriend, omg sweetheart that's the most heart warming compliment I've ever had and she sat on her lap and started deep tongue kissing her and I could see that mammoth cock starting to get aroused so I reached between my wife's butt cheeks and grabbed her cock and reached into the table and got out the baby oil and poured a bunch on her now semi soft penis and started rubbing it between Kelly's butt cheeks and it was getting bigger and bigger and bigger Holy fuck I'm thinking my wife is now using her pussy lips as a stroking toy and she's sliding back and forth and I got behind her and started caressing her breasts so I could watch my wife enjoying this beauty and she said oh wow that feels so incredible and I didn't let her finish and said sweetheart I would love to see you take her for the ride of your life and suddenly she pushes up and she reached between her legs and positioned it to be inserted but it wouldn't fit in
Back in the late sixties I was visiting a rock club in NYC. A lovely woman came to my table and asked if she could share the table with me because the club was so crowded she couldn’t find a seat. Yes, of course. The music was very loud and made it difficult to have a conversation so I told the lady I was going outside to smoke a joint “Would you care to join me?” She said she would like to so we left the club went outside and I lit a joint and we shared it while talking about the band we had just been listening to. After the joint was finished she asked me if I would like to go to her apartme
Back in the late sixties I was visiting a rock club in NYC. A lovely woman came to my table and asked if she could share the table with me because the club was so crowded she couldn’t find a seat. Yes, of course. The music was very loud and made it difficult to have a conversation so I told the lady I was going outside to smoke a joint “Would you care to join me?” She said she would like to so we left the club went outside and I lit a joint and we shared it while talking about the band we had just been listening to. After the joint was finished she asked me if I would like to go to her apartment for a drink and I accepted. We hailed a cab and on the way to her place she confesses to me she is transsexual. I wasn’t shocked, it was after all NYC but I told her I was straight and she smiled and said “Okay then no problem but just one drink?” “Of course I said, that would be great.” In her apartment we had a couple of drinks and some small talk and I told her I had to leave. She gave me a kiss on the cheek and I left. Thought about that night for many years wondering if I made a mistake by not staying with her.
Fast forward many years later, now married to a beautiful sexy wife. Our sex life was great, no problems, we enjoyed straight sex and oral on each other and I was satisfied. One evening while watching TV my wife is gently stroking my dick she asked if I had a fantasy that I wanted to explore, I said no I’m happy with our sex life but asked if she had her own fantasy, She said yes I do would you like to hear about it and I told her of course I would. “I want to fuck your ass?” I chuckled and said “that’d be a little difficult since you don’t have a dick” She left the room and came back totally naked except for a 10″ real looking cock attached to a strapon she was wearing. She stood in front of me with the dildo close to my face and asked “What do you think, can I fuck you with this?” I was a little short for an answer but I reached out and touched the dildo and said “We can try it but I don’t know, it’s awfully big. We went to the bedroom and I got undressed while she produced a bottle of lube saying “This will help” She fucked me good for about 30 minutes and I shot cum all over our bed without even touching my cock. She still continues to peg me after a couple of years, sometimes asking me to suck her cock.
My thoughts of the lovely trans lady in NYC returned after being fucked in the ass and sucking my wife’s dildo. I started looking at trans porn and came across several websites offering trans escorts but being with and having sex with a trans woman was still only a fantasy until I had to go to Amsterdam on business and I saw an opportunity. After arriving in Amsterdam and getting settled into my hotel room I started to search the internet on my laptop for trans escorts in Amsterdam and found a site that had exactly what I was looking for lots of photo’s and bio’s of some of the most beautiful trans women I have ever seen and I began my search. So hard to decide but after an hour or so I found a woman I liked. From the photo she was slim with long black hair, large breasts, beautiful ass and her ad claimed a “12″ cock loaded with cum for you.” perfect! I messaged her on whatsapp and told her I would like a date and what I needed to do to prepare. She didn’t reply for about an hour and I thought well, maybe she’s busy so I went to the hotel cafe for a coffee. While drinking my coffee I received a message from her telling me to just be clean inside and out and we agreed on 350 euro for one hour if I went to her place and 50 euro more if she were to come to my hotel room. I agreed on her coming to my room and we set a time. I went back to my room, showered and cleaned out my ass, put on a business suit and went to the hotel florist and bought a bunch of red roses to give her when she arrived.
Went back to my room and right on time I got a call from the front desk telling me I had a visitor, now I’m
getting a little nervous but when I heard a knock on my door I answered and there she was, absolutely stunning and my dick knew it. She entered the room and gave me a long passionate kiss. I handed her an envelope with the agreed upon amount and the flowers I had bought her and she smiled and gave me another long kiss. She broke the embrace and stepped back taking off her coat to reveal and amazing body dressed only in a bra and matching panties. She turned around and asked what I thought and I replied “You are absolutely beautiful!” and she reached o
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