Summarized texting conversation between Pete and Autumn (with Pete’s permission).
Sunday
Pete: Hi Autumn I’ll be in the area on Friday this week. Is there any chance we could meet? I really enjoyed our conversations.
Autumn: 3pm would work perfect for me. Would this work for you?
Pete: Yes! A couple of questions that I have. I wanted to try one of your famous strap on sessions. Should I bring my own gear? Is 2 hours enough?
Autumn: Absolutely. I ask everyone to bring their own toys for sanitary purposes. Make sure to get your own toy and harness. I can make suggestions if you wish.
Pete: I would really appreciate suggestions. This is all new to me.
Autumn: Have you ever tried a toy before? If so, what was the size?
Pete: I’ve tried a vibrating butt plug which was around 3cm wide and 7cm in length.
Autumn: There are two suggestions I like to make for first timers. This one here is great for someone who may feel a bit nervous psychologically, especially for the first time. The dildo is quite small (approximately the length and width of finger) and it is a very easy transition.
If you’re feeling a bit adventurous, I’d suggest this one here. It’s only about 2 inches at the top and gradually gets slightly wider. But I like this one because it’s not as scary as it looks (only 6 inches in length) and it has an amazing vibrating bullet that we can insert inside of it to vibrate the whole dildo.
Pete: thank you for the suggestions. I will pick one of these up. I’m also interested in role-playing. Is this something that we can do?
Autumn: what are you thinking?
Pete: I’ve never shared this fantasy with anyone, but I’ve always had a cuckolding fantasy. I was thinking a scenario with a therapist who I confess to, and who gently humiliates me about it.
Autumn: let’s try it!
Thursday
Pete: Hi Autumn. I was thinking I will skip the pegging session. I read your blog about your recommendation and we will stick with your magic fingers.
Autumn: That sounds perfect!
Friday
Pete: Hi Autumn. I’ve changed my mind again and I actually might pass by the sex shop and find a strap on set.
Autumn: Great. See you soon.
Pete arrives at his appointment time.
Pete (text)
Pete: Hi Autumn, I’ve arrived.
Autumn: Great! You can buzz me at ******. The direction to access my unit is ******* and my unit number is *****.
Pete walks down the hall carrying his black bag, trembling with excitement and uncertainty of what to expect and what will transpire this time.
Autumn greets Pete at the door with a hug, gently taking the bag off his hands. Autumn invites Pete to sit on the couch with her.
Now Autumn and Pete were face-to-face for Autumn to extract more information from Pete.
Autumn: So Pete. You mentioned a role-playing fantasy. Role-play is in typically something that I do, but I tend to do light role-play as it feels more natural than taking on a completely role of who I am.
Pete: I agree. I wasn’t hoping to have a complete role change. What I was hoping for was to find ways to share my fantasy and explore a little more as to what I like. I’ve been finding myself watching more cuckolding porn recently with humiliation. This is a big step for me as I have never shared this with anyone else. I actually only slept four hours the night before because of this confession. I wasn’t sure how this would be received.
Autumn: There is no judgment on my end, I want to assure you. This is very exciting for me and I would love to be the person to guide you through the psychological processes around what you like, what you don’t like and what you might be open to. Now when you say humiliation, what do you mean by that?
Pete: I fantasize about an ex-girlfriend or an ex-lover having sex, or playing with, a man who has a bigger dick than I do while I watch. I fantasize about her instructing me to help her or just having her watch and tell me that he is more of a man than I am.
Autumn: And what about blackmail? Is this something that you fantasize about?
Pete: I know that blackmail is one of the branches of humiliation, but this is not something that turns me on. I had a scenario with an ex-girlfriend where she kept looking at other men. Part of me was bothered by it, but then there was another part of me that was intrigued. I just wanted to know whether she wanted other men and there was something that was a little exciting about this, even though it also made me feel a little jealous at the same time.
Autumn: I noticed that you keep talking about your ex-girlfriends being part of the fantasy. Why is this?
Pete: In my married life, I am the dominant one. My wife is more submissive and I prefer for it to stay that way. Our sex life works very well because of this. But then the other part of me wants to experience the cuckolding fantasy, and become the submissive, and I don’t want her to be a part of it.
Autumn: That is totally fair. We all have different relationships with different people in our lives and sometimes one person can’t fulfill all of our needs. Would you think that I could fulfill that role and fantasy of the ex-girlfriend who cuckolds you? Would this be sufficient?
Pete: That’s a great question. It is something I will have to think about.
Autumn: Great. Take all the time that you need to figure that out. Now get on my massage table. It’s my turn to take charge.
Autumn directs Pete to lay face down on the massage table while she massages him. After some time, she takes the strap on out of the bag (similar to the first option that she suggested) and puts it on.
Pete: You look so hot wearing that.
Autumn instructs Pete to suck on it to get it ready.
Autumn: You must earn this pegging like a good boy.
Autumn flips Pete over onto his back and puts his legs behind his head. She slowly inserts the dildo into his ass while teasing and playing with his cock.
Autumn starts to talk to Pete while she’s fucking him.
I’m going to get a man with a bigger dick to come in my space and massage him in front of you. I’m going to make you sit over there on the white chair and you will not be allowed to play with yourself. I will make sure that I have a butt plug inserted inside of you while you watch so all you can do is feel the internal stimulation from the butt plug I’ve inserted. You have no choice, but to enjoy every little tingle of internal pleasure. I will have your hands tied up to make sure that you are a good submissive boy. After I flip him over, I want you to help me get his cock hard. I’ll instruct you to stroke him or suck his cock - depending on what I see fit. And you can’t say no. You will have to sit there and watch as I play with his cock. I will make sure that his cock is much bigger than yours so you know what a real man looks like. You will be at my beck and call for me when I need you to get men’s cocks hard for me and you will have to do everything I tell you.
Pete: Yes Mistress Autumn.
And with that, Pete blew his load with an orgasm more intense than ever felt before.
Final Message
Pete was nervous about trying pegging. I had a conversation with somebody yesterday about trying pegging with a new partner. First of all, there is no sensation in the dildo, but this doesn’t mean that I can’t be gentle. It’s about taking it slow as the giver and being calm and relaxed as the receiver. There has to be trust built-up, and a sense of comfort from knowing what to expect and how gentle your partner is.
Pete and Autumn ended up having a role-playing session, but it wasn’t in the traditional sense of taking on a totally different personality. Autumn still played the therapist, but this was part of who she is. She asked all the pertinent questions to get a better sense of his boundaries of what he liked, what he didn’t like, and what he may be open to. It was important to distinguish the difference between an ex-girlfriend and his current relationship with his wife, and how this all ties into his fantasy. It was also imperative to normalize this because the truth of the matter is that not everyone will fit into this role that we desire in our sexual interactions. And some people will.
For Pete, this was a big step for him to share this fantasy. Upon this reflection, I also wonder if there was a fear of being misunderstood by a person in his current relationship (with judgement) or him not truly understanding his own boundaries. What I mean by this is if he shared this with his ex-girlfriend (girlfriend at the time), would he have still enjoyed this fantasy or would jealousy have taken over (as this was one the emotions he felt at the time of watching his ex girlfriend look at other men). I wonder if the idea of it being someone who is not his wife makes it more erotic, taking the focus off jealousy and honing in on the physicality and sexual components of the experience.
For example, for many swinging couples it is not about being in a relationship with the other person (people). It’s all about the physical and sexual components. This is what makes it easier to enjoy the experience and to ensure things get less complicated with emotions. Boundaries are important in any sexual encounter. It’s important to understand what yours are for yourself so that we don’t cause harm and instead focus on the fun of it all, as it should be.
❤️
Incredibly hot!