Venturing Down Anal Lane


Any tips for doing anal for the first time?

Samantha, 33, WA


Dear Samantha,

RELAX. RELAX. RELAX! I cannot stress this enough. There seems to be a lot of anxiety and fear among anal virgins when the subject of butt sex comes up, but there really doesn’t need to be. Ultimately, what will make or break your first anal experience, is really YOU (provided your partner isn’t a jerk).

In my early 20’s, I tried anal sex with a man I loved very much and who was a really great, patient, gentle guy. We went through all the steps. I used an enema. We bought ample lube. We built up our expectations of our ‘first night of anal’ so exponentially that when it came time to do the deed – he couldn’t stay hard for very long. And during those times that he had a full-blown erection, it hurt too much for me to want to continue. Needless to say, it was a giant debacle.

Fast forward to my late 20’s. I was seeing a guy that I was insanely attracted too. Every little thing about him made me want to rip his clothes off. Late one night, after one of our dates, I took him home and we started having sex. It was incredibly hot and before I knew it, I had positioned his penis against my ass and within seconds we were having full blown anal. It was hot, passionate, and there was NO pain.

Now, before you start wondering whether it was SIZE that was an issue, I’ll tell you. It wasn’t. Both men were roughly the same size. The difference was that my second experience was much more relaxed. There was no expectation. No anticipation. It was just heat of the moment, passion.

However, anal sex isn’t always so easy for people and there are absolutely tools to help relax you before you delve into the wonder that is butt sex! You might want to consider buying a butt plug. Start small and work your way up. Butt plugs help you get used to the sensation of having something in your ass. They also help your butt muscles relax to the idea of being penetrated. NS Novelties has some incredible butt plugs in both body-safe TPE or Borosilicate glass. Find a shape and style that works for you! However, sometimes if you start too small, you can run into problems of the plug getting sucked UP your butt, so I am issuing a word of caution to you – if you are going to buy a small butt plug, make sure there is a finger hold (NS Novelties’ Jolie’s have this).

Also, don’t build up anal into a gigantic event. Let it happen naturally. If you like having a drink or two, or getting stoned, it might help take a bit of the edge off. Anal is a wonderful thing to experience with a person you trust. I highly recommend it and I hope some of this advice works for your venture down anal lane! Let me know!

Jacky St. James

Want to ask Jacky a question about love, sex, relationships, porn or the adult industry? Click here to submit your questions!


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Jacky StJameshttp://missjackystjames.com
Jacky St. James hails from the East Coast, graduating with a BA in Drama and Anthropology and is a multiple award winning adult writer and director for New Sensations. She is known for a wide-range of films from romantic comedies to edgier all-sex releases with her most acclaimed titles being: Torn, The Friend Zone, Power and Control, Love is a Dangerous Game, The Submission of Emma Marx, and Dear Abby. Torn, her most successful film to date, went on to receive Best Actor, Best Actress, Best Couples’ Release, and Best Screenplay award wins during the 2012 award season. During her career in adult, Jacky has been an advocate of couple's-oriented pornography and has been a guest speaker at UC - Santa Barbara, UCLA, AEE, XBIZ 360 and has been featured in several popular mainstream publications including Jezebel, Slate, and the Examiner. Jacky shares pictures, clips, and stories about her successes and debacles as a woman working within the adult industry on her website: missjackystjames.com From? An east coast, white-bred, conservative town Age? 36 Fav. Food? Sushi or Pizza! Although I will eat just about anything. Fav. Alcoholic Drink? I am not a drinker, but when I do drink, it's usually Chocolate wine! Fav. Book? Bright Shiny Morning by James Frey. I also am a fan of We Need to Talk about Kevin, The Count of Monte Cristo, and the Complete Works of Shakespeare Fav. Movie? It's a toss up between Miracle (about the 1980 US Hockey team defeating the Soviets) or Shawshank Redemption (which was cinematic perfection). One Fun Fact? I have a severe allergy to cooking. I'm working through it.
Venturing Down Anal Lane

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