Baring my soul here

Richard,
All good advice, thanks so much! And thanks for the encouragement.

Update: I’ve visited the SB a second time. I’m learning more about her. She’s a little uncomfortable talking with me about the delayed ejaculations. She loves having sex and is very playful. She definitely loves her orgasms and doesn’t have much trouble having them. She loves the penetrative sex and my thrusting drives her crazy but she’s not one for paying compliments. She tells me it feels so good and to not stop. I keep hoping she’ll pay me a compliment on my dick but I don’t think she’s going to do that.

This time was very similar to last time. I started caressing her while she laid on her back. Then I gave her nipples a lot of attention, just like I did with her before. Then I applied some lube and started manual stimulation on her clit. This time my erection happened while I was playing with her clit. I was so happy to see that (of course I had taken Cialis 7 hours before but still a quicker erection than last time). That’s progress! I had positioned myself better this time and didn’t get tired. When she asked for penetrative this time I was ready with my finger. I stroked her G spot and kept stimulating her clit like last time. She had two orgasms just like last time. The first one took about 5 minutes but second one probably took over 10. After the second one I went to a slow motion with both hands. She said it still felt really good. I did that for a few more minutes and then told her I was going to put on a condom. I reached over to the bed stand and grabbed a condom. She immediately started giving me oral. She has a very rough tongue which makes the sensations intense, not really in a good way but not too bad either (I’m uncircumcised). I put the condom on and said I wanted front entry on side of the bed, just like last time. I started going through my thrusts, just like last time, and she started going crazy, just like last time. I don’t think she’s faking it. My thrusting seems to get her close to orgasm. It took about 20 minutes but I had learned how to pace myself and be efficient in my positioning. She couldn’t quite get there and she was kind of in her own little world and not being coherent so I was just trying different things. The one that worked was to stop holding her legs up, lean forward with my forearms on the bed, put my pelvic weight onto her and start grinding. That pushed her over the edge. I was tired after that and told her I wanted to rest a minute. We lay side by side for a few minutes and talked. I took the condom off and asked for slow oral. She did a combined oral and slow handjob for about 15 minutes. Then we played out a porn video I like where the woman lies back against the headboard and the man straddles her and controls his penis in and out of her mouth. It didn’t get me there like I was hoping it would. Then I asked for a handjob with lube and me laying on my back. I asked her to do it slow. I had to play with my nipples but in about 5 minutes I ejaculated! This was quicker than last time and I didn’t have to masturbate myself. More progress! (but I wish I didn’t have to play with my nipples; not very masculine). I did have to close my eyes and keep them closed until I was spurting.

This time she had 3 orgasms compared to 4 last time. Her 4th the last time was when she masturbated while watching me masturbate. This time I also gave her the third orgasm without her having to go cowgirl and the hard grind. Overall this was a better session and not as physically strenuous on me.

My thoughts? I don’t think she will be a long term sex partner for me, but I also think she just might be the perfect partner for me at this moment. I’m having to step up to be with this woman, and I’m so happy to see I have the body and techniques to answer the call. If I didn’t have I really think this woman would’ve chewed me up and spit me out by now. But I can hang with her, and I think that speaks well towards my lovemaking future. She told me that the most orgasms she has ever had is 5. The first time I was with her she had 4. I think that’s pretty good on my part but she doesn’t pay compliments. I’m guessing she just doesn’t really think about it. She’s not a deep thinker either. She’s just a great girl to have fun with, and I appreciate her for that. And when she’s had her orgasms she will perform whatever act I want for as long as I want, so she’s not selfish at all. I’m grateful to have found her and for all that my experiences with her are teaching me.

How long do you think you’ll be staying in that SD/SB arrangement? While you’re getting some really interesting experience there, it’s not how most relationships work.

I also think you shouldn’t expect compliments or comments on penis size. You’re well above average (1.5x) and people here know well that most women don’t say anything about it. It’s almost as if they don’t care unless you’re too small/big.

MDC,
Thanks for the suggestions. Since I’ve only had sex 8 times, and since I am having unreliable erections and delayed ejaculations, my plan is to have weekly sex with a SB until I’ve resolved those issues, i.e. until I have reliable erections without the aid of Cialis and until I can ejaculate each time I’m with a woman. Then I’m going to seek out a romantic partner. That’s the plan…

I honestly thought women would pay their lovers compliments. I’m surprised to be finding out that’s not the case. I guess my ego is fragile because of my lack of experience but starting to realize I need to get over that.

Hey @WorthyQuest, I have some observations on Cialis that might be useful. I’ve taken it 11 times now, 20mg pill, and while my erections are solid as ever, I am finding that there is a bit of a delay in getting to orgasm/ejaculation. Its not that the stimulation I get feels reduced, or that there is a numbing effect like I’ve read some men say Cialis feels like to them. I think normally my erection changes in degrees of hardness during intercourse. In some positions I’m a little less rigid, like in doggie style, where my cock kind of has to “bend” a little while thrusting. I think that these slight natural variations make the stimulation feel different to my penis and the sensations are very intense when inside my wife. But on Cialis, my cock stays exactly the same hardness the whole time, and while it feels amazing, I notice that the sensations are not as intense on my penis. I figured this out during sex with my wife last night. I was “getting there” for my orgasm but it was like I could just keep thrusting nonstop and I had to really pump hard at the end to cum.

I know you have issues with delayed ejaculations and although Cialis is working for your erections, it might be helping delay your orgasm and ejaculation. I’m learning on Cialis as I use it and noticing how it feels more and more each week.

Thanks PM,
I’ve read in several articles that Viagra delays ejaculation, but I hadn’t read that Cialis does the same thing. If true that’s bad news for someone like me that needs Cialis for an erection but also has anxiety induced delayed ejaculations.

I’m making progress on the ejaculations, though. Not the direct path to normal I was looking for but I’m getting quicker each time IF I close my eyes and play with my nipples. I’m not doing any masturbation by myself. All my ejaculations are in the presence of a woman. I’m hoping this will train my body to be ready to ejaculate whenever I’m having sex with a woman. Hopefully soon I will be able to keep my eyes open and not play with my nipples. in my case it’s all anxiety induced (unreliable erections and delayed ejaculations) and not physical ED.

Update: I’ve had two more sessions with the SB. I’ve made progress. The progress is slow, steady, and I guess basically linear. It would probably make sense to a psychiatrist but it’s a mystery to me. I think it’s safe to say my issues (anxiety induced unreliable erections and delayed ejaculations) are subsiding a little bit with each session. I still have not been able to climax inside a woman but I definitely feel the arousal increasing and getting me closer with each visit. I’m fairly certain it will happen soon. Also, I still must close my eyes and play with my nipples to ejaculate. This is frustrating and embarrassing to me. I apologize to the SB each time before I do it. The good news is that I’m getting very close now without doing that, and when I do it it’s only a minute or less before I ejaculate. One of my strategies was to never masturbate. All my ejaculations now are when I’m with a woman. I’m getting my body accustomed to the thought that “if I’m with a woman it’s ejaculation time”. I’m a big fan of Cialis now. Once I figured out that I personally need 6 hours for it to work it’s magic it has been 100% reliable for me. The only side effects have been a mild headache and some face flushing. I’m contemplating a prescription for the daily 5 mg regimen.

I like this SB. She’s a kind woman who understands my sexual goals and has become a partner in this. And she’s a lot of fun too. I know a good SB is hard to find. So many of them are very young and daffy. But, a good one is worth searching for.

When I can ejaculate while inside a woman, and when I can ejaculate in the presence of a woman without having to close my eyes and play with my nipples, I think I will be ready to seek out a romantic partner. I will hang onto the SB until I know I have found a solid romantic relationship. Then I will have to say goodbye to the SB; I’m a one-woman guy. I’m dropping one requirement I had placed on myself before seeking a romantic relationship, and that was to be able to have reliable erections without using Viagra or Cialis. I now think there is nothing with taking Cialis, and I see it as enhancing my erections and my penis.

Its been months, how is it going?! Still with the same SB? Are you ejaculating the way you want to now; have you started to become a better lover, too?? Hope all is well!

Porn is fucking toxic man. Had issues in my own life with it as well. Very desensitizing indeed.