First penetration feelings?

[Guest Holly Lace]

So I don't know how many women here were virgins when they were married, but I was. Married very young, right out of high school, my first ever sexual experience beyond masturbation was with my husband. We made love on our wedding night and it hurt a little obviously when he penetrated me and broke my cherry. It was very intense, very intimate, and to my mind at the time he was going to be the one and only man ever to do this to me. Now obviously a man can't take my virginity again but in a way that's what happened on our first swing.

 

I'm saying all this because I'm curious the other experiences women may have had, that first time another man was inside you.

 

For me, I was laying on my back on a large soft couch. I'd worn some very nice new lingerie, black and purple, a teddy, one piece with little purple lace frills around the legs and arms and nearly sheer. I'd also shaved and waxed for the first time ever in my entire life so...that was a new thing too. The man I was with was a good friend, and my husband and his wife were on the other end of the couch but I couldn't really see them.

 

My friend was about the same size as my husband in length but he was much thicker. I can remember he was kinda surprised I was bald down there and he loved touching it and licking it, which was an amazing sensation to fee, though I will admit I felt bad later because I'd denied my husband the privilege of having my bald pussy first. He had to settle for sloppy seconds, if you'll forgive the crudeness.

 

When he held my legs up I was shaking I was so nervous. I mean...this was for real, another man was going to be INSIDE ME! Only my husband had ever been inside, had ever felt that kind of pleasure of me but now I was going to share it and I was terrified. I'd been taught, in a way at least, that what I was about to share was sacred and intimate and only for my husband so to give it away to another man, stranger or friend, was just something I could barely wrap my head around.

 

Feeling his penis touch my vagina that first little second made me break out in a sweat, an honest thick sweat. It had me embarrassed. Then feeling him push, and my vagina open for him, part of me thought maybe it couldn't like maybe it would just stay shut like a locked door, my husband the only one with the key but...my labia opened, my pussy stretched for him, my juices were still as slick if not more so and he entered me slowly. He did that deliberately, went slow, almost like he thought he'd hurt me. And like I said he was much thicker so I had to stretch to get him in properly.

 

Being honest it had my stomach churning but also I was shaking with intense pleasure as he entered me. And though he wasn't any longer than my husband it felt like he went deeper. I couldn't believe when he was completely in and his balls were resting against my butt. I was breathing so rapidly you'd think I was having an asthma attack. I was shaking so hard just having this new man in me I couldn't believe it and then...to my utter embarrassment, he pulled out just a little and I came. It was a really intense orgasm too. It made me wet enough and must have excited him enough because he started a slow steady pace.

 

Anyway, that whole night is for another time but, I wanted to get the ladies and I guess the men too, thoughts on this. What was it like? Did you feel bad? Like you were betraying your husband? Was it good for you, bad, indifferent?

[sunbuckus 3,567]

Holly Lace said:

...I wanted to get the ladies and I guess the men too, thoughts on this. What was it like? Did you feel bad? Like you were betraying your husband? Was it good for you, bad, indifferent?

 

If I really think back to how I felt about how marriage = monogamy when we first married, I may have felt similar to how you felt if I hadn't reconciled myself that marriage =/= monogamy several years ago. Mr. Sun and I had a bit of a tumultuous few years in the beginning of our marriage that had me come to the conclusion that monogamy isn't something that comes naturally to humans. Can some humans be monogamous? Of course! But I don't think it's natural--it's a social conditioning.

 

But you asked how it felt during our first full swap and when I was being first penetrated by the other husband. Well...(okay, I had to cheat on this one, I had to re-read what we wrote during our first time at our blog--we both posted our own perspectives on that night)...I don't think I was as "prepped" as I think I could have been. Maybe it was nerves and the uncertainty of whether I was attracted to the other husband since we barely spoke ten sentences to each other before swapping. But I do remember feeling weird to the point of having to pretend that Mr. Playmate was Mr. Sun to calm myself down. The only other times I had had sex was when there was an emotional attachment. Obviously, this was the first time where it was purely sex. I barely knew this other man's name or much about him and here we were fucking.

 

I didn't feel like I was betraying Mr. Sun though because I've done that in the past and this was nothing like that. Mr. Sun not only knew, but encouraged me to fuck this other man. He was right there for me to hold his hand (and I did) when we swapped. I could see and hear his pleasure and he could do the same for me. We went to the party together. We explored the party together. We swapped in the same room, on the same bed, together. We left the party together. We were both on the same page. There was no lying. No dishonesty. No sneaking home with a pussy full of sperm. No forgotten condom wrapper on the dresser. I didn't feel sick to my stomach or develop an eye tick from all of the hiding.

 

It was awesome in that we were able to experience this one event together that most couples would never be able to. As Mr. Sun stated, "What happened...was right out of a porno." How many people can claim that? It excited us for weeks afterwards. We couldn't stop grinning at this secret of what we had done that weekend where ever we went. Most of all, it helped to rebuild up some of the trust in Mr. Sun that I had lost a few years before. So, yes, it still remains to be the best swinging experience we've had just because it was our first time and how it positively affected our relationship.

[GoldCoCouple 4,065]

Screw the question, please finish writing the rest of your story! Smokin'.

[afterwork 89]

Long story how it happened, but when he entered me he was built entirely different than the only othe cock (my hubby of then seven years) that I had in me. I was overcome by the excitement of this new cock and the whole concept of swinging which up to then I had only read about in the Penthouse Forum magazines (circa 1972). I don't know where my screams of passion came from as he pounded deep in me, nor did I know I could come more than once before he did, but it was a whole different loss of virginity that overwhelmed me.

 

It was nice hearing my husband satisfying the other wife as well in the living room. The next level of virginity loss came when we did the full swap laying next to each other. Years later with a different couple, I discovered my loss of my bi- virginity as we ladies kept going after the guys had both came in our pussies. Only regret is that we waited too many years to start swinging.

[GuyInMD79 1,500]

Holly Lace, thank you for this post. As someone fairly new to the site, you've really "made a splash" with this post! Your post has an interesting mix of emotional and physical impressions.

 

You asked for guys to comment as well, so I though I'd chime in. When the Mrs. and I had our first swinger sex experience, we had been married and monogamous for 20 years. Also, I had not used a condom in many years! We were invited to come to the home of an experienced lifestyle couple, after having had a great dinner with them previously. We knew that this was a no-shit play date, and we were very nervous the whole evening. To our great fortune, this couple knew just when to go slow, and when to take charge a little- and they took charge once they understood that we did want to play, despite our nerves, but were just unsure how to move things in that direction.

 

So, the emotional... The four of us were all together on the same bed. Our nerves were reduced once we got going (we were much more familiar with the actual fucking than we were with the part about seducing a couple!), but we were still not completely relaxed. We still didn't really know how we would feel, seeing and hearing our spouse having sex with someone else. As it happened, the Mrs. and the other guy were moving quickly, and I got to be first to see my spouse getting fucked by somebody else. There was no jealousy, actually, and I was pleasantly surprised to find that I had no bad feelings at all. Just a big turn-on seeing and hearing her pleasure, of course, and also something unexpected- I felt genuinely happy for her, and also very proud of her for being so bold and adventurous! Bolstered by those good feelings, I felt that I could now concentrate more on pleasing and being pleased with the other woman.

 

As for the physical... As I said, this was the first time I had used a condom in probably 15 years! Because of that, and perhaps a little performance anxiety, I was not as hard as I would have liked. When I entered the woman, it felt good- no question about that! But the woman's pussy was very different from my wife's, and extremely tight. So tight, in fact, that, combined with the other issues, I had a little trouble maintaining an erection. She and I had had a good time when I'd gone down on her before we got to the fucking, and I was surely excited now that I had my cock inside her. She felt so different and exciting, and I could see that this was one of the great things about swinging! Alas, though, I was unable to cum with her that night, despite how turned on I was. So that night wasn't a complete success, but all four of us had a great time anyway. And I've since vindicated myself with this woman, and we've played several more times- to very pleasurable completion!

 

So to sum up, we did not feel bad, or like we were betraying each other at all when we had that first penetration by and with our swinging friends. We felt like we were taking a daring adventure together, and sharing the experience made it all the better!

[Sophy 569]

We started as a soft swap couple only, so we had enough time to discuss our experiences and prepare our transition to full swap.

For us the development of the entire situation was smooth and very satisfactory.

 

I do remember the cold feeling of the penetration, he was wearing a condom and some lubricant he put on top, plus I have orgasmed seconds ago from oral so I was wet and hot. I think I even said something like: "oh my God is cold" or something like that, he was a regular-size guy so in a couple of seconds we archived full penetration.

[Shore2Please 610]

It put a smile on my face when I saw this question posed. I wanted to answer last night but instead slept or didn't sleep reliving that first time.

 

I was not a virgin when I married, I also wasn't with that many that I can't remember my firsts of all my sexual life. The first time I was "felt up", the first time I was touched down there, the first time touching a guy, The first time making a guy cum, by hand. I remember the first time I blew a guy. I think most of us remember that. I of course remember my FIRST time. Can almost see that in my head now. Wasn't great but I "loved" him. Wondered if the pain would go away. We had sex many times, don't remember it ever being great but I am sure at the time it was. Only had a few sexual partners before meeting my husband. My first time with my husband I remember well, just like I remember my other first times. I remember it being a great night. Looking back I wasn't thinking he was the one I would marry. I am happy I did though. We have a great marriage. Our sex life has been great together and we have experimented privately over the years. He is a great man, a great husband, a great father and a great sex partner. I never though I would have sex with anyone but him. That changed on a cruise. I have written about it before in other threads. The question is how was the first time being with that new man.

 

When we decided to swap partners for the night I was excited. My memory might have changed a little due to drinking that night, but I was excited. My new partner was a gentleman in a good way. We had been naked on a beach that day so him undressing me was strange but I thought he already saw me. He then seduced me, not rushing into anything. My first penetration by him was his hand. I melted. His second was with his mouth. The next was me taking him in my mouth. My first penis in all these years. Shape, scent and taste was different than y husband. I enjoyed making him moan and I enjoyed the different way he was doing things to me. When he did finally penetrate me I was ready. I don't remember thinking this was wrong. I was ready for it. I will not say it was better than anything I did before, but it was different

[findinganswers 369]

I will answer from a guy's point of view. Maybe our situation is different, we had our first experience with friends who were very experienced. I admit to the nervousness. On the hand we were with best friends who tried to take the edge off. Did I want to fuck my wife's best friend? You betcha. Everything was done with a laugh and a joke in a good way. Took the edge off for me. After some mutual oral play, she got on top of me. So the first penetration was really her taking me in. For us, we didn't use condoms. I did have some thoughts on that. We know we are clean, they are active, so we did take a chance. I had asked if they were sure and her answer was just have fun. I know after I was in, she joked about me liking it. She just sat on me with short rocking. Then a few more and stopped. I did worry about finishing before starting. Don't laugh, I was picturing her in a bathing suit on the beach in my mind, rather than naked and fucking. Damn, this was our friend. I tried to cum and when I knew I was going to I wanted to pull out. I didn't. How did I feel? Like I wanted to fuck her again.

[oc1234 435]

I am answering from a male's perspective too. Like findinganswers, our first time was with our best friends. We had known them for 6 years. With no warning, the male of the couple went from massaging my wife to having intercourse with her. My wife and I had never even discussed that possibility, although I have to admit I had wanted to fuck my friend's wife for years. I was massaging my friend's wife at the time, and she whispered for me to look at her and my wife going at it across the room on the carpeted floor. I immediately started massaging those parts of her body that I had been avoiding, which led to us having intercourse. My main thought at the time was the fear that she would change her mind and stop before I came. She didn't but it still caused me to come earlier than I really wanted to.

[willyoats 324]

Our first experience, after about 25 years married, was with a couple who ran a (now defunct) swing club in Florida. Some of you may remember Bob and Nancy in Zephyr Hills. They invited us on a Thursday night to be initiated into the lifestyle before attending the weekend party. After a couple of hours of chat, we split up to have our first experience. I was playing with Nancy for a while and she with me. I gave her an orgasm with tongue, fingers and vibrator. Then it was time for that first penetration into someone other than my wife. I remember very little of the physical sensation, other than that it felt good, rather like every time I went into my wife. Nancy was soft, warm and welcoming, so physically it was not really unique. What I remember was the emotional sensation: here I am with another woman, a fantasy that I had dreamed of and anticipated for a couple of years. The overwhelming sense of satisfaction at being able to overcome the anxiety and ENJOY the experience was the "take-away".

 

Meanwhile, my wife was with Bob, who showed her a new positions that was very pleasing. We used it many times in the following years.

 

Interestingly , all the time I was with Nancy, I never thought about my wife being screwed by another man I hardly knew.

 

We stayed for the weekend party and had a really good time with new partners. That was the beginning of the best era of our sex lives.

[Eddiem 139]

I asked my wife about this our first time having a new person (friend) join in. She said it was strange at first as she never thought of that person that way but as his cock teased her pussy she said it felt strange but her pussy was pulling his cock in... and in the end as he was thrusting he pulled out and she put it back in to let him finish in her. She said it was strange having another man cum in her and she did visualise his cum filled with sperm in her. Very erotic.

[Numex 2,409]

The first time for my wife after we married was with an ex, then another ex, with my encouragement. So for both of us, it was exciting but without anxiety. A good way to start.

[couplers 4,615]

It felt like something that I deserved. It was a feeling of empowerment that I was fucking them on my terms. Even more so because they both knew about the other and still wanted me anyway. At my request, they met. They were monogamous with me even though I didn't ask, probably because I gave them both as much sex and love as they could handle. In time we began relationships with other women because I wanted it. It also freed me from my stifling religious upbringing.

[JessicaJamison 861]

I was honestly a little mad at my husband my first time, he had asked me to try being a "Hotwife" and I was hurt by that.  I was intent on not doing it until I ran into a guy that I had been crushing on hard since I had known him, and then that tiny voice in my head said you can do it, he gave you a hall pass.  The flirting came naturally and before I knew it we were making out and stripping out of our clothes and he was inside of me.  The sensations were over whelming and I had a couple of intense orgasms which quieted the voices of doubt or guilt.  When I was done I felt good.  When I got home and realized I needed to tell my husband what I did, the butterflies were enough to make me sick.  But he had said he want ed it so I did it, he was over the top excited and begged me to keep going.  I had sex with that man all sex with that man all summer long, and it was great..

[Half MT 218]

On 3/3/2016 at 7:13 PM, Guest Holly Lace said:

So I don't know how many women here were virgins when they were married, but I was.

I was a virgin bride too. Pain, blood, we got it done. I was afraid of the pain but waited my whole life for the moment. No orgasm from me, I still loved it. 

 

On 3/30/2016 at 9:13 AM, Shore2Please said:

The first time I was "felt up", the first time I was touched down there, the first time touching a guy, The first time making a guy cum, by hand. I remember the first time I blew a guy. I think most of us remember that. I of course remember my FIRST time. Can almost see that in my head now. Wasn't great but I "loved" him. Wondered if the pain would go away.

Perfectly said. Remember all those firsts too. 

 

On 3/30/2016 at 9:13 AM, Shore2Please said:

My first penetration by him was his hand. I melted. His second was with his mouth. The next was me taking him in my mouth. My first penis in all these years. Shape, scent and taste was different than y husband.

Pretty sure that was the same here with my husband watching and the wife and him busy. What I remember was they had accents, not from the USA. He also was different in penis was the first I ever saw uncircumcised. My husband insisted that I go first.  He later said he wanted to make sure I didn’t back out if he did it and I would be mad at him. 
Before doing anything I told them I squirted, I said I peed sometimes, they corrected me. The last thing he did before penetration was some very good oral and then he lifted my legs onto his shoulders and in he went. Pretty sure I closed my eyes, it was different only because he was different. I concentrated not to pee/squirt, maybe that took my mind off of what we did. Timmy said I moaned and looked like I orgasmed, I didn't think I did but I enjoyed. I eventually did and I eventually squirted. I eventually also did other firsts with them. Too bad we’ll never see them again. 

[couplers 4,615]

On 11/20/2020 at 3:06 PM, JessicaJamison said:

The sensations were over whelming and I had a couple of intense orgasms which quieted the voices of doubt or guilt.

Funny how that works. 

 

On 11/20/2020 at 3:06 PM, JessicaJamison said:

When I got home and realized I needed to tell my husband what I did, ... he was over the top excited and begged me to keep going. 

Funny how that works too.

 

Sex, and life in general is much better without the religious and social constraints and guilt.